Nomenclatura

PRINCIPALES GRUPOS FUNCIONALES EN ORDEN DE PRIORIDAD

Cuando un compuesto tiene dos o ms grupos funcionales, su nombre base tendr la
terminacin del grupo con mayor prioridad y el otro grupo ser un sustituyente.
Grupo funcional

Frmula
O

cidos carboxlicos

Orden de Prioridad

steres

O
O

Halogenuros de cido

carboxi-

Anhdrido -oico
-ico
-ato de
alquilo

alcoxi-carbonil-

halogenuro de
-ilo

halogeno-alcanoil-

-amida

carbamoil-

-nitrilo

cianoformil-

Amidas

NH2

R-C=N
O
H

-al

(carbaldehido)

Cetonas
R

Alcoholes
Mercaptanos
Aminas

O
O

cido -oico
-ico

OH
O

R
O

Anhidridos de cido

Nitrilos
Aldehidos

Sufijo

Cuando el grupo
es un sustituyente
se nombra como:

R-OH
R-SH
R-NH2

-ona

oxo-

-ol
-tiol
-amina

hidroximercaptoamino-

-ilo

halogeno-alcanoil-

O
Amidas
PRINCIPALES GRUPOS FUNCIONALES
EN ORDEN DE
PRIORIDAD
-amida
carbamoilNH2

...con-nuacin
Nitrilos

-nitrilo
cianoR-C=N
Cuando
un compuesto tiene dos Oo ms grupos funcionales, su nombre
base tendr la
Aldehidos
formilterminacin del grupo con mayor prioridad y el -al
otro grupo ser un sustituyente.
(carbaldehido)
H
R
Cetonas
Grupo funcional

Frmula

Orden de Prioridad

Alcoholes
cidos
carboxlicos
Mercaptanos
Aminas
Anhidridos
de cido
teres
Sulfuros
Alquenos
steres
Alquinos
Halogenuros
Nitro
Halogenuros de cido
Alcanos

O
R-OH
R-SH
OH
RR-NH
2
O
O
R-O-R
R-S-R
R
O
R
R-CH=CH-R
O
R-C=C-R
R
O
R R-X
R-NO
O 2
R-H
R

-ona

Sufijo

-ol
-tiol
-ico
-amina
ter
-ico
sulfuro
-eno
-ato de
-ino
alquilo
halogenuro de
-ano
-ilo

Cuando el grupo
es un sustituyente
oxose nombra como:
hidroximercaptocarboxiaminoalcoxialquiltioalquenilalquinilalcoxi-carbonilhalgenonitroalquilhalogeno-alcanoil-

Para nombrar a los cidos carboxlicos

y a los anhidridos es necesario anteponer la palabra
O
Amidas
cido y anhidrido respectivamente, seguido del
nombre de la cadenacarbamoilhidrocarbonada con
-amida
NH2
R
el sufijo -ico.
Nitrilos
-nitrilo
cianoR-C=N
O
Aldehidos
formil-

C6Hsuch
e are
five constitutional
isomers
with molecular
formula
now and
14 . We
tinually
revised by the
commission
since then.
Names
as are
isobutane
C
name
three
of
them
(hexane,
isohexane,
and
neohexane),
but
we
cannot
name
neopentanenonsystematic namesare called common names and are shown in red
CH
CH2new
CH2names
CH
CH3C
er two
without
defining
names
structural
now,
ignore
the under2CHare
2CHshown
3units. CH
3CHCH
2CH
2CH
in this
text. The
systematic
or3for
IUPAC
in(For
blue.
Before
we3 can
name:
Nomenclatura
Alcanos
written
blue.)
standinhow
acommon
systematic
name for anhexane
alkane is constructed, we
must
learn how to name C
CH
3
hexane

systematic name:

alkyl substituents.

CH
2CHCH
2CH
33
CH33CH
CHCH
2CH
2CH

CH3CH2CH2CH2CH2CH3

2.1

name:
name:

isohexane
2-methylpentane
CH3

neo
2,2-dim

CH3CH
CH3CCH
CHCH
33
2CH

Nomenclature
of Alkyl Substituents
hexane

CH3CH
CH3
CHCH
3
3 3
3-methylpentane
2,3-dimethylbutane
3-me3lpentano
isohexane
neohexane
Removing a hydrogen from an alkane
results in an alkyl2,3-dime3lbutano
substituent
(or an alkyl
group). Alkyl substituents are named2-methylpentane
by replacing the ane 2,2-dimethylbutane
ending of the alkane with
yl. The letter
RCHCH
is usedCH
to indicateCH
anyCH
alkylCHCH
group.
CH CH
Hexano
hexane

CH3

CH3 CH3CH2

CH
CH2CH
CH33CH
3 2

agrupo
methyl
group
an
ethyle3lo
group2,3-dimethylbutane
a grupo
propylpropilo
group
m3-methylpentane
e3lo
grupo

R
any
alkyl
group
grupo
alquilo

CH3CH2CH2CH2
agrupo
butylbgroup
u3lo

Table 2.2

methyl
me3lo

Names of Some Alkyl Groups

sec-butyl
sec-bu3l

CH3

CH3CH2CH

CH3
Section
2.1 Nomenclature of Alk
CH CCH
neopentyl
neo-pen3l
3

ethyl
e3lo

CH3two of
CH3
CH3CH
C7H 16 . We can name only
There
are2 nine alkanes with molecular formula
(heptane
and isoheptane) without defining
new structural
units. Notice
that
neo- A2compound
hexyl
CH3CH
CH2
propyl themCH
CH3
propilo
hex3l
can
2CH2CH2CH
3CH2CH2
heptane cannot be used as a name because three different heptanes have a carbon that name, but a nam
CH3CHCH2CH2CHcompound.
isohexyl
isopropil
CH3CHto four other carbons
isopropyl
tert-butyl
tert-bu3l
iso-hex3l
2
3C
is bonded
and aCHname
must specify only
one compound.
CH3
CH3
CH3CH2CH2CH2CH2CH2CH3
CH3CHCH2CH2CH2CH3
pen3l
pentyl heptane
CH3CH2CH2CH2CH2
CH2
CHcommon
3CH2CH2name:
CH3
systematic name:
heptane
CH
isopentyl
CHCH
CH
iso-pen3l
CH
CHCH
3
2
2
3
2
isoheptane
CH3

bu3l
butyl
isobu3l
isobutyl

2-methylhexane

CH3

CH3

CH3CH2CHCH2CH2CH3
CH3

3-methylhexane

3-me3lhexano
CH3

CH3CCH2CH2CH3
CH3

2,2-dimethylpentane

2,2-dime3lpentano

CH3CH

CHCH2CH3

CH3 CH3

2,3-dimethylpentane

3,2-dime3lpentano

CH3CHCH2CHCH3
CH3

CH3

2,4-dimethylpentane

2,4-dime3lpentano

CH3
CH3CH2CCH2CH3
CH3

3,3-dimethylpentane

3,3-dime3lpentano
CH3 CH3

CH3CH2CHCH2CH3
CH2CH3

3-ethylpentane

3-e3lpentano

a butylhave
groupa hydrogenanremoved
isobutyl group
a sec-butyl
group
a tert-butyl
group
groups
from a primary
carbon.
A sec-butyl
group has
a hydrogen removed from a secondary carbon (sec-, often abbreviated s-, stands for secondary),
anda astraight-chain
tert-butyl group
hasgroup
a hydrogen
removed
fromn
a tertiary
carbon (tert-,
A name of
alkyl
often has
the prefix
(for normal),
to
sometimes
t-, stands
forantertiary).
A tertiary
is adoes
carbon
emphasize
thatabbreviated
its carbon atoms
are in
unbranched
chain. Ifcarbon
the name
not that
haveis
bonded
to three
carbons.
Notice that
thethe
isobutyl
group
theunbranched
only group chain.
with an
a prefix
such
as nother
or iso,
it is assumed
that
carbons
are inisan
iso structural unit.

CH 3CH 2CH 2carbono

CH 2Br primario
carbono primario

CH
3CH 2sCH
2CH 2F
carbono
ecundario

carbono terciario

a primary carbon
a primary carbon
a secondary carbon a tertiary carbon CH3
butyl bromide
pentyl fluoride
CH3CH2CH2CH2 or
CH3CHCH2
CH3CH
CH3C
or2CH
n-butyl bromide
n-pentyl fluoride

CH3

CH3

u3lo
agrupo
butyl bgroup

angrupo
isobutyl
group
isobu3lo

agrupo
sec-butyl
group
sec-bu3lo

CH3

a grupo
tert-butyl
group
tert-bu3lo

Like the carbons, the hydrogens in a molecule are also referred to as primary, secondary, and tertiary. Primary hydrogens are attached to primary carbons, secondary
A name of a straight-chain alkyl group often has the prefix n (for normal), to
hydrogens to secondary carbons, and tertiary hydrogens to tertiary carbons.
emphasize that its carbon atoms are in an unbranched chain. If the name does not have
a prefix
such as n or iso, it is assumed
that the carbons are in an
unbranched chain.
hidrgeno primario
hidrgeno terciario
hidrgeno secundario
primary hydrogens

CH3CH2CH2CH
CH
2OH
3CH 2CH 2CH 2Br
butyl bromide
or
n-butyl bromide

tertiary hydrogen

secondary hydrogens

CH3CHCHCH
2OH
3CH 2CH 2CH 2F CH3CH2CHOH
CH3

pentyl fluoride
or
n-pentyl fluoride

CH3

Like the carbons, the hydrogens in a molecule are also referred to as primary, secondary, and tertiary. Primary hydrogens are attached to primary carbons, secondary

A
ca
tw
bo

CH2

2
2
The systematic
name
of 2an alkane is2 obtained
the following rules:
H2C using CH
2
CH
H2C CH2
H
C
CH
H
C
CH
2
2
2 the number
2
2
1. Determine
of carbons
in the longest
continuous carbon chain. T
cyclopropane
cyclobutane
cyclohexane
chain is called thecyclopentane
parent hydrocarbon.
The name that indicates the number
carbons in the parent hydrocarbon becomes the alkanes last name. For exa
Cycloalkanes
are almost always
writtenhydrocarbon
as skeletal structures.
Skeletalwould
structures
Nomenclatura
Alcanos
ple, a parent
with eight carbons
be called octane. T
show the carboncarbon bonds
as
lines,
but
do
not
show
the
carbons
or
the
hydrogens
longest continuous chain is not always a straight chain; sometimes you have
bonded to carbons. Atoms other
carbon
and hydrogens
to chain.
atoms other
turn than
a corner
to obtain
the longest bonded
continuous
than carbon are shown. Each vertex in a skeletal structure represents a carbon. It is un1- Se designa la cadena de carbonos
8
7
6
5
4 3
2
1
8
7
6
5
4
derstood
to CH
the
appropriate
number
of hydrogens
to CH
giveCHCH
ms
larga. that each carbon is bondedCH
CH
CH
CHCH
CH
CH
CH
CH
CH
3
2
2
2
2
2
3
3
2
2
2
2CH3
the
carbon
four
bonds.
2- Se numera la cadena de tal
CH3
CH2CH2CH3
manera que el sus-tuyente le
3
2
1
4-methyloctane
4-me3loctano
4-ethyloctane
corresponda la numeracin ms
three different alkanes with an 4-e3loctano
eight-carbon
parent
hydrocarbon
baja.
3 - S e n o mcyclopropane
b ra e l c o m p u e cyclobutane
sto
cyclopentane4 3 cyclohexane
2
1
indicando el nmero donde se
CH3CH2CH2CHCH2CH2CH3
Acyclic
also dbe
encuentra
el smolecules
us-tuyente can
seguido
e represented by skeletal structures. In a skeletal strucCH2CH2CH2CH3
ture
of ande
acyclic
molecule,
lines. Again,
la
nombre
la cadena
principal the carbon chains are represented
5
6 by
7 zigzag
8
4- Si hay dos o ms sus-tuyentes, se
each vertex represents a carbon, and carbons are assumed
to be present where a line
4-propyloctane
4-propiloctano
nombran
en ends.
orden alfab-co
begins or
2. The name of any alkyl substituent that hangs off the parent hydrocarbon is ci
before the name of the parent hydrocarbon, together with a number to design
the carbon to which the alkyl substituent is attached. The chain is numbered
3
1
5
3 the direction
1
that gives the substituent as low a number as possible. The s
2
stituents name and the name of the parent hydrocarbon are joined in one wo
6
4
4
2
and there is a hyphen between the number and the substituents name.

butane
butano

2-methylhexane
2-me3lhexano

3-methyl-4-propylheptane
3-me3l-4-propilheptano
1

CH3CHCH2CH2CH3

6-ethyl-2,3-dimethylnonane
6-e3l-2,3-dime3lnonano
5

CH3CH2CH2CHCH2CH3

The rules for naming cycloalkanes resemble the rules for naming acyclic alkanes:
CH3

CH2CH3

1. In the case of a cycloalkane with an attached

alkyl substituent, the 3-ethylhexane
ring is the par2-methylpentane

3
3
numbers indicating
the locations
of theNotice
identical
together,
separated
by commas.
that substituents
there must beare
as listed
many numbers
in a name as
CH
CH
CHCH
CHCH
CH
CH
CH
C
CCH
CH
separated by commas.
Notice
that
there
must
be as
3
2
2
3 many numbers
3
2
2in a name2as 3
there are
substituents.
there are substituents.
CH
CH
CH CH

rs are separated by a

2,4-dimethylhexane

CH3CH2CHCH2CHCH3

CH3 3CH3

CH3 3,3,4,4-tetramethylheptane
CH3
CH3CH2CH2C

CCH2CH3

The2CHCH
prefixes
di, tri,
tetra,CH
sec,
and
tert
ignored
in alphabetizing
substituent
CH3CH
2CHCH
3 CH
3CH
2CH
2C areCCH
2CH3CH
CH
CH
3

groups, but the2,4-dimethylhexane

prefixes iso, neo, and cyclo
are not ignored.
3,3,4,4-tetramethylheptane
CH3

CH3
CH3 CH3
2,4-dimethylhexane
3,3,4,4-tetramethylheptane
d tert are ignored in
CH3
3 and tert are ignored in alphabetizing substituent
2,4-dime3lhexano
3,3,4,4-tetrame3lheptano
The prefixesCH
di,2CH
tri,3tetra,CH
sec,
groups,
prefixes
iso, neo,2CH
and2CH
cyclo
are CH
not3ignored.
CH3but
CH
CCH
CH2CH
2the
2CH
2CHCHCH
2CHCH2CH2CHCH3
Theinprefixes di, tri,
tetra,
sec,
and
tert
are ignored
in 3alphabetizing
substituent
are not ignored
and tert are ignored
groups,in but the prefixes iso, neo,
and
CH2CH
CHCH
CHCH3 CH3
2CH
3 not ignored.
33 cyclo
3are
3,3,6-triethyl-7-methyldecane

o are not ignored in

CH2CH3 CH3CH
CH23CCH2CH2CHCHCH2CH2CH3

CH3CH2CH
CH3 2CH2CHCH3
2CHCH
CH
3
5-isopropyl-2-methyloctane

CH2CH
CH3CH
CH2CH3 CH CH CH CHCH CH CHCH
CHCH3
CH3CH2CCH2CH2CHCHCH
2
2
3
3
2
2
2
2
3
3,3,6-triethyl-7-methyldecane
3,3,6-trie3l-7-me3ldecano
4. CH
WhenCH
both
directions lead to the same lowest
number forCH
one
3 of the substituents,
CH
CH
CHCH
2

the direction is chosen

3,3,6-triethyl-7-methyldecane

5-isopropyl-2-methyloctane
that gives the lowest5-isopropil-2-me3loctano
possible
number to one of the reCH3
maining substituents.
Los prejos di, tri, t4.etra,
When both directions lead to the same
lowest number for one of the substituents,
5-isopropyl-2-methyloctane
sec, y tert NO son the direction is chosen
CH3 that gives the lowest possible
CH3number
CH2CH
to 3one of the reconsiderados
en directions
el orden
maining
4. When both
leadsubstituents.
to the
lowest number for
the substituents,
CHsame
CH3one
CH2of
CHCHCH
3CCH2CHCH3
2CHCH2CH3
alfab3co.
E
n
c
ambio
l
os
the direction is chosen that gives CH
the lowest possible number to
of the
reCHone
CH
3 CH
3
2CH3
CH
CH
3
3
3
prejos
iso, neo,
y ciclo SI
maining
substituents.

2,2,4-trimethylpentane

6-ethyl-3,4-dimethyloctane

CH3CCH2CHCH3
CH36-e3l-3,4-dime3loctano
CH2CHCHCH2CHCH2CH3
2,2,4-trime3lpentano
not
not
CH
CH
CH
3
2
3
2,4,4-trimethylpentane
3-ethyl-5,6-dimethyloctane
CHno
CH3 no
3 CH3
because 2 < 4
because 4 < 5
3-e3l-5,6-dime3loctano
2,2,4-trimethylpentane
6-ethyl-3,4-dimethyloctane
2,4,4-trime3lpentano
CH3CCH2CHCH
CH3CH2CHCHCH
3
2CHCH2CH3

son considerados en el
CH3
orden alfab3co
5.

not
2,4,4-trimethylpentane
If CH
the3 same
CH3 substituent numbers
CHare
3
because 2 < 4

cited receives the

2,2,4-trimethylpentane

not
3-ethyl-5,6-dimethyloctane
obtained in both directions,
because 4 < 5

lower6-ethyl-3,4-dimethyloctane
number.

the first group

The common names of alkyl halides consist of the name of the alkyl group, folsecondary alkyl halide
tertiary alkyl halide
lowed by theaname
of the halogenwith athe
ine ending of the halogen name replaced by ide (i.e., fluoride, chloride, bromide, iodide).

primary alkyl halide

common names of alkyl halides consist of the name of the alkyl group, folCH3CHof
CH3CHI
3Cl
2F the halogen
Nomenclatura
hCH
alogenados
by the
name of thecompuestos
halogenwith
the ine ending
name remethyl
chloride iodide).
common name:
ethyl fluoride
by ide (i.e., fluoride,
chloride,
bromide,
CH3
systematic name:

chloromethane

CH3Cl

on name:
tic name:

CH3CH2F

fluoroethane

CH3CHI

CH3CH2CHBr
CH3

isopropyl iodide
sec-butyl bromide
CH
CH
CHBr
2-iodopropane
2-bromobutane
3
2

methyl
ethyl fluoride
CH3
CH3
Cloruro chloride
de me3lo
Fluoruro
de E3lo
In
the
IUPAC
system,
alkyl
halides
are
named
as
substituted
alkanes.
The
substituent
chloromethane
fluoroethane
clorometano
Fluoroetano
isopropyl
iodide
sec-butyl
bromide
Bromuro bromo,
de sec-bu3lo
de isopropilo
prefix names for the halogens end withYoduro
o (i.e.,
fluoro, chloro,
iodo).
2-iodopropane
2-bromobutane
2-bromobutano
2-
y
odopropano
Therefore, alkyl halides are often called haloalkanes.

CH3
CH3named as substituted alkanes.
UPAC system, alkyl halides are
The substituent
ames for the halogensCH
end
with o (i.e., fluoro, chloro,
CH3CCH2bromo,
CH2CH2CHiodo).
3CH2CHCH2CH2CHCH3
2Cl
ore, alkyl halides are often called haloalkanes.
CH3

Br

2-bromo-5-methylheptane
2-bromo-5-me3lheptano
CH3

CH3

CH3CH2CHCH2CH2CHCH3
Br
2-bromo-5-methylheptane

1-chloro-5,5-dimethylhexane

1-cloro-5,5-dime3lhexano

CH3CCH2CH2CH2CH2Cl
I

CH3

2-e3l-1-yodociclopentano
1-ethyl-2-iodocyclopentane

PROBLEM 10

CH

1-chloro-5,5-dimethylhexane

CH2CH3

Br

Cl
CH3

Br4-bromo-2-chloro-1-methylcyclohexane
1-bromo-3-cloro-4-me3lciclohexano
Cl

methyl f

same compound.)

PROBLEM 6
Ejercicios:
theesystematic
for eachcompuestos
of the following compounds:
1. Give
Indique
l nombre de name
los siguientes
CH3

CH3

a.
a) CH3CH2CHCH2CCH3

f. CH3CH2CH2CHCH2CH2CH3
d)
CH3CHCH2CH3

CH3

CH3 CH2CH2CH3
b.
b) CH 3CH 2C(CH 3)3

g. CH3C
e)

CHCH2CH3

CH2CH2CH3

c) CH 3CH 2C(CH 2CH 3)2CH 2CH 2CH 3

c.

f)
h. CH3CH2CH2CH2CHCH2CH2CH3
CH(CH3)2

CH3
d. CH3CHCH2CH2CHCH3
CH2CH3

b. CH3CH2CHCH2CHCH2CH3

d. CH 3CH 2CH 2CH 2OCH 3

PROBLEM
9de los siguientes compuestos
2. Indique
el nombre
Give the systematic name for each of the following compounds:

a)
a.

c
e. CH3CHCH2CH2CH3
)

CH2CH3
CH3

b)
b.

d)
f.

CH2CH3

CH2CH3

CH2CHCH3
CH3
c. H3C
H3C
d.

g.
CH2CH3
h. CH3CH2CHCH3

rections, the
correct
name
is the4-pentoxy-1-butene
name that contains the lowest substituent num1
3
5
7
ber. For example, 2,5-dimethyl-4-octene
is a 4-octene
the longest
CH3CH2CHCHCH
CHwhether
2CH
2
7
6
5 4 3
2
1
3. continuous
If a chain has
more
than one substituent,
substituents
are cited
in alphabetical
chain
is numbered
from 5-bromo-4-chloro-1-heptene
left tothe
right
or from right
to left.
If you num3,6-dimethyl-3-octene
order,
using
same the
rules
for alphabetizing
that you learned
Section
(The
ber
from
left the
to right,
substituents
are at positions
4 and 7,inbut
if you2.2.
number
Nomenclatura Alquenos
prefixes
sec,
andare
tertatare
ignored2group
inand
alphabetizing,
but
neo,diand numcyclo
rightdi,
totri,
left,
they
positions
5.
Of is
those
fouriso,
substituent
4. Iffrom
the same
number
for
the
alkene
functional
suffix
obtained
in
both
rections,
correct
nameso
isthe
thecompound
namenumber
that contains
theassigned
lowest substituent
num- and not
are not
The
appropriate
then
to each substituent.
bers,
2 the
isignored.)
the
lowest,
is is
named
2,5-dimethyl-4-octene
ber.
For example, 2,5-dimethyl-4-octene is a 4-octene whether the longest
4,7-dimethyl-4-octene.
Br Cl
4
6
8
continuous chain1 is2numbered
3
5 from7 left to right or from right to left. If you numCHto
CHCH2CHCH
CCHnumber
3CH
2CHthe
2C substituents
3 positions
3CHCH
2CH3
ber from left
right,
are at
4CH
and
7, but
if
you
CH3CH2CHCHCH
CH
CH
2
2
7 5. Of
6 those
5 4 four
3 substituent
2
1
from right to left, they CH
are at positions
2
and
numCH
Br
CH
3
3
3
3,6-dime3l-3-octeno
3,6-dimethyl-3-octene
5-bromo-4-chloro-1-heptene
bers, 2 is the lowest,
so the compound is named
2,5-dimethyl-4-octene
and not
5-bromo-4-cloro-1-heteno
2,5-dimethyl-4-octene
2-bromo-4-methyl-3-hexene
4,7-dimethyl-4-octene. not
not

4. If the same number

for the alkene functional group
suffix is obtained in both di4,7-dimethyl-4-octene
5-bromo-3-methyl-3-hexene
CH3CH
C CHCH
CHCH
CH3CHCHtheCCH
2because
2CH
rections,
the2CH
correct
name
lowest
num2 <2is
4 the 3name that contains
because
2 <3substituent
3
ber. For example,
is aBr 4-octene
CH32,5-dimethyl-4-octene
CH3
CH3 whether the longest
5. In
cyclic alkenes,
is not
needed
to
denote
the position
of the
function2,5-dimethyl-4-octene
continuous
chain ais number
numbered
from
left to2-bromo-4-methyl-3-hexene
right
or from
right to left.
If you
numnot
2,5-dime3l-4-octeno
albergroup,
because
the the
ringsubstituents
is always numbered
so not
that
the7,double
bondnumber
is befrom left
to
right,
are
at
positions
4 and
but if you
2-bromo-4-me3l-3-hexeno
4,7-dimethyl-4-octene
5-bromo-3-methyl-3-hexene
tween
carbons
1 and
2.
from right
to because
left,
they
at positions 2 and 5.because
Of those
2 < are
4
2 < 3four substituent numbers, 2 is the
lowest, so the compound
is named 2,5-dimethyl-4-octene
and not
CH3
2
5 CH3
5. In4,7-dimethyl-4-octene.
cyclic alkenes,3 a CH
number
is not needed
to denote the position of the function1
2CH3
1
al group, because the ring is always
numbered
so that the double bond is be4
2
CH3CH
CHCH2CHCH3 CH
CH3CHCH CCH
2CH2C
33
tween carbons
CH2CH
3
2CH
5 14 and 2.
3

3-ethylcyclopentene
4-ethyl-3-methylcyclohexene
CH3 4,5-dimethylcyclohexene
CH
Br4-e3l-3-me3lciclohexeno
CH3 CH3
3-e3lciclopenteno
4,5-dime3lciclohexeno
2
5 3 CH3
1
CH
CH
3
2
3
2,5-dimethyl-4-octene
2-bromo-4-methyl-3-hexene
1
4
2
In cyclohexenes, the
not double bond is between C-1 and
not C-2, regardless of
CH
CH
3
2CH3
4 4,7-dimethyl-4-octene
5-bromo-3-methyl-3-hexene
whether5 you
move around the3 ring clockwise
or counterclockwise.
Therefore,

PROBLEM 4

Ejercicios:
Draw the structure for each of the following compounds:
1. Ea.
scriba
la estructura de:
3,3-dimethylcyclopentene

c. ethyl vinyl ether

d. allyl alcohol

b. 6-bromo-2,3-dimethyl-2-hexene
a) 3,3-dime-lciclopenteno
b) 6-bromo-2,3-dime-l-2-hexeno
PROBLEM 5
2. Indique el nombre de los siguientes compuestos
Give the systematic name for each of the following compounds:
a. CH3CHCH

CHCH3

d. BrCH2CH2CH

CH3

CCH3
CH2CH3

CH3
b. CH3CH2C

CCHCH3

e. CH3

CH3

CH3 Cl
c. Br

f. CH3CH

CHOCH2CH2CH2CH3

Draw the structures and give the common and systematic names for the seven alkynes
molecular formula C6H 12 .

PROBLEM 4

3. Indique el nombre de los siguientes compuestos

Give the systematic name for each of the following compounds:

a. BrCH2CH2C
b. CH3CH2CHC
Br

c. CH3OCH2C

CCH3
CCH2CHCH3

d. CH3CH2CHC

Cl

CCH2CH3
CH

CH2CH2CH3

PROBLEM 5

Which would you expect to be more stable, an internal alkyne or a terminal alkyne? W

6.2

Physical Properties of
Unsaturated Hydrocarbons

All hydrocarbons have similar physical properties. In other words, alkene

alkynes have physical properties similar to those of alkanes (Section 2.9). All a

a symmetrical ether

33
CH
an unsymmetrical ether
CH
3
CH3CHCH
CHCH2OCCH
OCCH

CHOCH
OCHCH
CH
CH3CH
CH2OCH
OCH2CH
CH3
CH
CH
3
2
3
33
2 2 33
3
2
2
3
ethyl
methyl
ether
diethyl
ether
yl ether
ethyl methyl
diethyl
ether
Theether
common name
an ether
of the names
two
alkyl substitue
CH
CH
3 of the
3
often of
called
ethyl consists
ether
CH
CH
3
3
often called
ethylby
ether
alphabetical order),
followed
the word tert-butyl
ether. The
smallest
isobutyl
etherethers are alm
Nomenclatura (in
teres
tert-butyl isobutyl ether
CH3 by their common names.
alwaysCH
named

ix

ta

CH3CHCH2CH2O
CH3CHOCHCH2CH3
CH3
CH
CH3CHOCHCH
CH
3CHCH2CH2O
2
3
R-O-R CH3 CH3OCH2CH3
CH3CHCH2OCCH3
CH3CH2CH
OCH
3 2CH3
CH
CH
3
3 isopropyl
cyclohexyl
isopentyl ether
sec-butyl
ether
ethyl methyl
ether
diethyl
ether
e3l
m
e3l

ter
CH3
cyclohexyl
isopentyl ether CH3
sec-butyl
isopropyl
ether
often die3l
calledethyl
ter ether
Grupo funcional
tert-butyl isobutyl ether
tert-bu3l
isobu3l
ter
The
IUPAC system names anCH
ether as an alkane with an RO substituent.
The subter
3

The IUPAC
systembynames
an ether
as an
alkane
an RO
substituent.
The substituents
are named
replacing
the yl
ending
in with
the name
of the
alkyl substituent
CH2alkyl
O
CH3CHOCHCH
stituents
are named by replacing
the yl
name
of 2the
substituent
3CHCH
2CH3ending in theCH
with oxy.
l ether
with coxy.
teres
omo sus3tuyentes
CH3
CH3

neglect the prefix

e symmetricalCH O
3
ake this oversight a
methoxy
CHmetoxi
3O

methoxy

CH
CH3
CH3CH2O
CH3CHO
CH3CH2CHO
CH3CO
The
IUPAC
system
names
an
ether
as
an
alkane
with
an
RO
substituent.
The su
CH3ethoxy
CH
CH3CHO
CH3CH2CHO
CH
2O
3CO
etoxi
CH3 the yl endingCH
CHalkyl
stituents
are named by replacing
in 3the name of the
substitu
3
ethoxy
isopropoxy
sec-butoxy
tert-butoxy
CH3
CH3
CH3
with oxy.
isopropoxi
sec-butoxi
tert-butoxi
sec-butyl isopropyl ether

isopropoxy

cyclohexyl isopentyl ether3

sec-butoxy

tert-butoxy

CH3CHCH2CH3
CH3CH2CHCH2CH2OCH2CH3
CH3CHCH
CH3
CH3CH2CHCH
2CH2OCH2CH3
CH
CH3OOCH32 CH
CH
O
CH
CHO
CH3CH2CHO
3
3
2
3
2-methoxybutane
1-ethoxy-3-methylpentane
methoxy
ethoxy
OCH3
CH
3
CH
CH3
3
2-methoxybutane
2-metoxibutano

1-ethoxy-3-methylpentane
isopropoxy
sec-butoxy
1-etoxi-3-me3lpentano

CH3CHOCH2CH2CH2CH2OCHCH3
CHCHCH
CH3
CH3CH2CHCH2CH2OCH2CH3
CH3CH
CHOCH
CH3 3
2 2 2CH
2CH2OCHCH
CH3 3

CH3

CH3CO
CH3

tert-butoxy

2-ethylpentan-1-ol
3-butoxypropan-1-ol
Alcohols are compounds
in which
of3 an
OH a hydrogenCH
OHalkane has been replac
4,4-dimethyl-2-pentanol
OH3-bromo-1-propanol
group. Alcohols are4-chloro-2-butanol
classified as primary,
secondary, or tertiary, depe
whether the OH group is bonded to a primary, secondary, or tertiary carbon
4. If way
theAsame
number
the
functional
group
obtained
both directions,
The for
longest
continuous
chainsuffix isThe
longestincontinuous
chain
Nomenclatura
lcoholes
alkyl
halides
are
classified.
has six carbons, but the longest
has four carbons, but the longest

group
ctional
sible

he
e

up
ets

oup
onal
le

hols

butan-2-ol

the chain is numbered in the direction that gives a substituent the lowest possible
chain
continuous
chain containing
number. Notice continuous
that a number
is containing
not neededthe
to designate
the position
of a func-the
R
R
OH functional group has five
OH functional group has three
tional group suffix
in
a
cyclic
compound,
because
it
is
assumed
to
be
at
the
carbons so the compound is
carbons, so the compound is
1-position.
OH
named
a pentanol.
named
a propanol. R C OH
R asCH
OH
R
CH as
2

R-OH

R
CH3
Grupo
3. fIfuncional
there
is a functional
group
suffix and a asubstituent,
the
functionalagroup
suffix
a alcohol
primary
alcohol
secondary
alcohol
tertiary
CH3CHCHCH
CH
primario
alcohol
talcohol
erciario
alcohol
2CH
3
3CH2CH2CHCH2CHCH
3 secundario
alcohol
gets the lowest possible number.
Cl OH

OH

CH3

OHof the alkyl group

The common name of an alcohol consists of the name
2-chloro-3-pentanol
2-methyl-4-heptanol
CH3
3-methylcyclohexanol
the
OH not
group is attached,
followed
by
the
word
alcohol.
not
not
1
2
3
4-chloro-3-pentanol
HOCH2CH2CH2Br

4
3
2 1
6-methyl-4-heptanol
ClCH2CH2CHCH3

5 4 3
2 1
5-methylcyclohexanol
CH2CCH2CHCH3

OH
CH3 OH
5. If there
is
more
than
one
substituent,
the
substituents
are
cited
in alphabetical
3-bromo-1-propanol
4-cloro-2-butanol
4,4-dime3l-2-pentanol
CH3CH2OH
CH
CH3CHOH
3-bromo-1-propanol
4-chloro-2-butanol
4,4-dimethyl-2-pentanol
3CH2CH2OH
order.
ethyl alcohol

CH3

CH3CCH2

propyl alcohol

CH3
CH3
4. If the sameCH
number
for the functional group
obtained
in bothCH
directions,
CH3 isisopropyl
CH2suffix
HO alcohol
neopentyl alco
3
2CH3
the chain is numbered in the direction that gives a substituent the lowest possible
CH3CHCHNotice
CHCH
2CHCH2that
3
number.
a number
notthe
needed
designate
the position
of a func-In an alc
H3is
C is
OH to of
The functional
group
center
reactivity
in a CH
molecule.
3
tional
compound, because 3,4-dimethylcyclopentanol
it is assumed to be at the
Br group suffix
OH in a cyclic
2-ethyl-5-methylcyclohexanol
2-e3l-5-me3lciclohexanol
3,4-dime3lciclopentanol
OH
is
the
functional
group.
The
IUPAC
system
uses a suffix to denote cert
6-bromo-4-ethyl-2-heptanol
1-position.
6-bromo-4-e3l-2-heptanol

tional groups. The systematic name of an alcohol, for example, is obtained b

ing
the ethat
at the
end of
name of
the parent
with the suffix
Remember
the name
of athe
substituent
is stated
before hydrocarbon
the name CH
of the
3 par-

CH3

CH3

1,4-diisopropoxybutane

Section
2.7 2.7
N
Section

Ejercicios:
PROBLEM 13
12
PROBLEM
PROBLEM 13

a. Give the systematic (IUPAC) name for each of the following ethers:
Draw
the structures
of a homologous
seriesseries
of alcohols
that have
fromfrom
one to
Draw
the structures
of a homologous
of alcohols
that have
onesixtocarbons,
six carbons,
and a)
then
give
each
of3them
a common
namename
and
systematic
name.
1.andCH
CH
CHCH2CH2CH3
then
give
each
of them
a common
systematic
3OCH
2CH
f)3. aand
3aCH
2CH2CH2name.
OCH3

PROBLEM
14 14
PROBLEM

CHof
OCH
CH
CH 2whether
CH 2whether
CH 3eacheach
2.Give
4. CHname,
3CH
3 compounds
3CH 2name,
2OCH
Giveb)
each
the2of
following
a systematic
and
indicate
is a is a
each
the2CH
following
compounds
ag)systematic
and2indicate
primary,
secondary,
or tertiary
alcohol:
primary,
secondary,
or tertiary
alcohol:

c)a.3CH
a. CH
CH23CH
CH22CH
CH22CH
CH22OH
CH 2OH
b.

hd. CH
CH3CHCH
d. 3CHCH
2CHCH
2CH32CH3
2CHCH
)
CH3 CHOH
OH
3

d
)b.

CH3 CH3

CH3CHCH
e. 3CHCH
i)e. CH
2CHCH
2CHCH
2CH32CH3
2CHCH
2CHCH

CH3 CHOH
OHCH3 CH3
3

HO HO
CH3 CH3

e
CH32CCH
CH22Cl
CH2Cl
c. CH
CH22CH
)c.3CCH
OH OH

j)f.

f.

Cl Cl

CH23CH2
CH3CH

OH OH

PROBLEM
PROBLEM
15 15
the structures
the tertiary
alcohols
molecular
formula
H 14
O, give
and give
WriteWrite
the structures
of allofthealltertiary
alcohols
with with
molecular
formula
C6HC
and
146O,

mented
shark, for
dish in3 Iceland,
1
1 example,
2
3
4 a traditional
5
6
2
1 smells exactly like tr
CH3CH2CHylamine.
CH3primary
CH2CHCHamines,
CH
2CH2NH2There are
2CH2CHsecondary
3
3CH2CHand
2NCH
2CH3
amines,
tertiary
amines.
1-butanamine
classification depends onNHCH
how many
alkyl groups are bondedCH
to 3the nitrogen. Prim
2CH3
or
amines have oneN-ethyl-3-hexanamine
alkyl group bonded to the nitrogen,
secondary amines have two,
N-ethyl-N-methyl-1-propanamine
butan-1-amine
Nomenclatura
Aminas
or
or
tertiary amines have three.
4

N-ethylhexan-3-amine

N-ethyl-N-methylpropan-1-amine

R
R
R-NH
2
The substituentsregardless
of whether they are attached to the nitrogen or to the
NH

NH

NH

3
2
parent hydrocarbonare
listed ainprimary
alphabetical
order,
and then a number or
an N is
ammonia
amine
a secondary amine
a tertiary amine
primariain the amina
amina
terciaria
amoniaco
secundaria
assigned
to each one.
The chain amina
is numbered
direction
that gives the
functional
Grupo
funcional
group
suffix the lowest possible number.
amina
Notice that the number of alkyl groups attached to the nitrogen determines whethe

amine is primary, secondary, or tertiary. For an alkyl halide

CH3 or an alcohol, on the o
hand,4 the3 number
2
1 of alkyl groups attached
1
2to the
3 4carbon
5
6to which the halogen o
CH2NHCH3the classification
CH3CH
CHCH
3CHCH2determines
2CHCH22.4
OH CH
is bonded
(Sections
and3 2.6).
Cl

NHCH2CH3

nitrogen is attached N-ethyl-5-methyl-3-hexanamine

carbon is attached
3-chloro-N-methyl-1-butanamine
3-cloro-N-me3l-1-butanamina
N-e3l-5-me3l-3-hexanamina
to one alkyl group
to three alkyl groups

Br
5

4
3
2 1
CH3CHCH
CHCH
R 2C NH32

CH3R
NCH3

4-bromo-N,N-dimethyl-2-pentanamine
4-bromo-N,N-dime3l-2-pentanamina
a primary amine

R CH2CH3

ClNHCH CH CHR
2
2
3

OH

2-ethyl-N-propylcyclohexanamine
2-e3l-N-propilciclohexanamina
a tertiary
alkyl chloride
a tertiary alcohol

Nitrogen compounds
with
fourofalkyl
groups
bonded
nitrogenthereby
giv- bonde
The common
name
an amine
consists
of to
thethe
names
of the alkyl groups
ing the nitrogen
a positive
formal chargeare
called quaternary
ammonium
salts.
the nitrogen,
in alphabetical
order, followed
by amine. The
entire name
is writte
Their names consist of the names of the alkyl groups in alphabetical order, followed

The simplest ketone

O is called acetone. Other simple, commonly encountered ketones
C by
H their common names. These are derived by naming the alkyl or aryl
are usually called
179.5
yde (propanal)
CH
CH
C carbonyl
H
3 to 2the
groups attached
group. 48.8

27-11 A

Nomenclatura Aldehdos y Cetonas

O C H
O
179.5
s called acetone. Other simple, commonly encountered ketones
CH3 are
C derived
CH3 by naming
CH3 the
C alkyl
CH2or
CH
3
common names. These
aryl
rbonyl group.
acetone
methyl ethyl ketone

27-11 Aldehydes and K

TABLE
SomeAldehydes
Simple Aldehydes
and Ketones
CH3CH27-9
CH2CH3 of27-11
2 C Properties
diethyl Name
ketone
Common

Formula

TABLE 27-9 Properties of Some Simple Aldehydes

O
O
one is called acetone. Other simple, commonly
encountered
ketones of Some O
TABLE 27-9 Properties
Simple Aldehydes
O names.Grupo
Normal bp (C)
y their common
These are
derived O
by naming the alkylCommon
or aryl Name
funcional
Grupo Formula
funcional
H C H
formaldehyde
(methanal)
O
C
CH
C
3
Common Name
Formula
the CH
carbonyl
C group.
CH CH
CH CH
C CH CH
Cetona
Aldehdo Normal bp (C)
3

cyclohexanone
methyl ethyl ketone

acetophenone
benzophenone
O
diethyl ketone
formaldehyde (methanal)
(methyl phenyl ketone)
(diphenyl ketone)

!21

O
O
CH3!21
C H
H C H
formaldehyde
(methanal)acetaldehyde (ethanal)
O
O
O
CH3
CHThe
CH2CH3names
CH
CHderived
3 Csystematic
3CH
2 C are
2CH3 from their parent hydrocarbons. The
for
ketones
O
O
C CH3
C
CH3 C H
acetaldehyde (ethanal)
20.2
suffix
-one
added to the characteristic
stem.
methyl
ethylisketone
diethyl ketone
e3l me3l cetona
die3l
cetona (ethanal) propionaldehyde
CH3CH20.2
H
CH3 (propanal)
C H
acetaldehyde
2C
O
acetophenone
benzophenone
O
O
(methyl phenyl ketone)
(diphenyl ketone)
etanalCH CH C H propanal
O
propionaldehyde
(propanal)
48.8
O
O CH
O
3
2
3
1
2
3
4
1
2
3
4
5
6
O
C CH3
C
C H
C CH CH
CHfrom
CHparent
CH
CH3 (propanal)
CH
CH
CH3H
48.8
O
3 Ctheir
2 propionaldehyde
3
2 2C
for ketones are derived
hydrocarbons.
The2 benzaldehyde
3CH
butanone
4-methyl-3-hexanone
one
benzophenone
characteristic acetophenone
stem.
butanona
C H
O
(methyl phenyl ketone)
(diphenyl ketone) benzaldehyde
179.5

Steroid molecules have s

H
O excellent
CH3 benzaldehyde
The ketones are
solvents. Acetone is very useful because itCdissolves
most molecular
benzaldehido
179.5 shapes but diff
names4 for organic
ketones
are 2derived
Theis widely used as a solvent in the
1
3 from
4 is their
5 parent
6 hydrocarbons.
compounds
yet
miscible
with
water. Acetone
biochemical functions. P
H
CH3 stem.
CH2 C CH CH2 CH3
to2 theCH
characteristic
The simplest
called
acetone. Other simple, commonly
3
manufacture
of lacquers, paint removers, explosives,
plastics,ketone
drugs,isand
disinfectants.
(top), a female sex hormo
ne
4-methyl-3-hexanone
are
usually
called
by their
common
names.
are derived
by nam
4-me3l-3-hexanona
Theused
simplest
ketone
is called
acetone.
Other
simple,These
commonly
encountered
Some ketones
of high molecular weight are
extensively
in
blending
perfumes.
Structestosterone
(bottom), a km
are usually
called
by their
common
names. These
by naming
groups
attached
to
the carbonyl
group.are derived
hormone.
Boththe
are alkyl
ketono
tures of some naturally O
occurring
and
ketones
are molecules
O
CH3 aldehydes
Steroid
have
similar
groups
attached
to acetone.
the carbonyl
group.
4
1 is very
2
3 The
4 simplest
5it dissolves
6
lent3 solvents.
Acetone
useful
because
most
ketone
is called
Other
simple,
commonly encountered ketones
molecular shapes
but
different
C CH CH
C CH CH CH
CH
CH

 Cl, Br, O(CO)R, OR, NH 2 , NHR, or NR 2) that can be replaced

by a nucleophile. Acyl halides, acid anhydrides, esters, and amides are all called
carboxylic acid derivatives because they differ from a carboxylic acid only in the nature of the group that has replaced the OH group of the carboxylic acid.

Nomenclatura Acidos Carboxlicos y Derivados

compounds with groups that can be replaced by a nucleophile

BRUI17-669_730r3 28-03-2003 2:25 PM Page 671

O
R

O
R

OH

a carboxylic acid

Grupo funcional

O
R

OR

an ester

cido
Carboxlico

O
O

an acid anhydride

Anhdrido
de cido

Ester

Sec

compounds with groups that can be replaced by a nucleophile

O
R

O
Cl

O
Br

an acyl chloride an acyl bromide

acyl halides

O
NH2

O
NHR

amides

NR2

Haluros de Acilo
Amidas
Halogenuros de cido
Class II carbonyl compounds are those in which the acyl group is attached to a
group that cannot be readily replaced by another group. Aldehydes and ketones belong
to this class. The H and alkyl or aryl ( R or Ar) groups of aldehydes and ketones cannot be replaced by a nucleophile.

Grupo funcional

cannot be replaced by a nucleophile

O 3
CH

OBr

common
C name:

acetic anhydride
C
a
symmetrical
OCH2CH3 O CH CHCanhydride
O
3

acetic group
formic
a carboxyl

anhydride
C carboxyl groups are frequentlyC
shown in abbreviated forms
a
mixed
anhydride
CHC
OCH
3CHCH2
3 C

carboxyl oxygen
OCH2CH3 C

H
OH
OH
CH3CH2CH2O
OH
OH CH
O3CH
O
3
C
CCH
Carboxylic
acids
in which
a carboxyl group
is 2attached to a ring are named
by adding
Brbutanoic
systematic
name:
methanoic
ethanoic
acid
acid
acid
CH2CH
CH3CH
OH
CHgroup
OH
CH
OH
3
2that has
3acid
2 place
carboxylic
acid
tomethyl
thethe
name
of group
the cyclic
Take
aacetic
careful
look
atpropanoic
the
to make
sure that
An
ester
isC
aarboxlicos
compound
an OR
in
of
OH
of compound.
a following
carboxylic
c name:
ethyl
ethanoatename:
3-bromobutanoate
ethyl examples
cyclohexanecarboxylate
phenyl
propanoate
common
formic
acid
acid
propionic
acid
butyric
acid
cidos
C
C
C
ethanoic acid
propanoic acid
butanoic acid

EstersC

you u
n name:
ethyl acetate
methyl
phenyl
(R)
acid.
In naming
an propionic
ester, theacid
name
of propionate
the group
attached
to-bromobutyrate
the carboxyl
is CH
difference
between
systematic
(IUPAC)
and CHCH
common nomenclature:
acetic
acid
butyric
CH
OCH
OCH3
CH
Ooxygen
Oacid
3
2CH3
3
2
3CH2
COOH
stated first, followed byOthe name of the acid, with ic acidOreplaced by ate.COOH O
O

COnamed in the same way. The cation is named first, followed

COOH
Salts ofOcarboxylic acids are
O
O
OH
C
O
Br
CH
C
C
C
3
carbonyl
oxygen
the Cname of
the acid,
again
C with ic acid replaced by ate.
C systematicby
name:
ethyl
ethanoate
methyl 3-bromobutanoate
e
phenyl
C
OH
CH
CH C OHOH
CH
CH
CH
CH
CH
CH
CH
OH
CH
OHCHpropanoate
OH2
2 CH
2
2 CH22 CH
3
2
2
2CH
OH
OH
CH
CH
CH
CHCH
OH
CH
2CH2CH2 3
3
2 3
3
2 COOH 2
common name:
methyl
phenyl
CH
OethylOacetate
rial:
O propionate
O -bromobutyrate
systematic
name:
2-methoxybutanoic
acid
3-bromopentanoic
acid
cyclohexanecarboxylic
acid
trans-3-methylcyclopentanecarboxylic
1,2,4-benzenetricarboxylic
pentanoic
acid
hexanoic
acid
cido
p
entanoico
propenoic acid
benzenecarboxylic acid
anoic
acidof carboxylic
propenoic acid
benzenecarboxylic acid
enclature
cido
2
-metoxibutanoico
acid
acid
cido
b
enzoico
cido
1
,2,4-
common
name:
-methoxybutyric
acid
-bromovaleric
acid
C
proic acid
acrylic acid
valeric
acid
caproic
acid
acrylic acid
acid
C
Cbenzoic
C benzoic acid
cido
valrico
and their derivatives
R
OR

+ Salts of carboxylic
-metoxibu3rico
+acids are named in
cido

theOsame
bencenotricarboxilico
H
O Na
CH3
O K
Na+ way. The catio

2CH3

ate
e

Acyl Halides

by the name of the acid, again with ic acid replaced by ate.

The
group
a carboxylic
called
a carboxyl
group.
carboxyl
oxygen
3-D M
Acyl
halides
arefunctional
compounds that
haveof
a halogen
atom in acid
place is
of the
OH group
of a
systematic name: sodium
methanoate
potassium
ethanoate
sodium
benzenecarboxylate
trans-3
carboxylic acid. The most common acyl halides are acyl chlorides and acyl bromides.
common name:
sodium formate
potassium acetate
sodium
benzoate
O
O Tutorial:
penta
O
O and replacing ic acid with yl
O chloAcyl halides are named by using the acidOname
Brride (or yl bromide). For acids ending with carboxylic acid, carboxylic acid is
Acetic
of carboxylicC
C
C Nomenclature
C
CO
H
COOH
replaced
with carbonyl
(or bromide).
CyclicCH
esters
are called
lactones.chloride
In systematic
nomenclature,
they are named
C as 2
COCH
OCH
CH3CH2 acids
O and
their derivatives
2CH3 +
3CHCH2
3
OH
2-oxacycloalkanones. Their common names are
name
the
H derivedOfrom
CH
O K+
Nathe common
3 ofO
carboxyl groups
are frequently
a carboxyl group
carboxylic acid, which designates the length of the carbon chain, and
a Greek
letter to forms
shown
in abbreviated

steres

O
O
C
indicate the
carbon
to which the carboxyl
oxygen
is attached.
Thus,
four-membered
methyl
3-bromobutanoate
ethyl
cyclohexanecarboxylate
phenyl propanoate
CH
ciclohexanoato
d
e
e
3lo
etanoato
dring
e ethanoate
p
3
Clotasio
3-bromobutanoato
d
e
systematic
name:
sodium
methanoate
potassium
propanoato
d
e
f
enilo
methyl
-bromobutyrate
phenyl propionate
C
C
b-lactones
lactones are
(the carboxyl
oxygen is on the b-carbon
), five-membered
common
sodium
CH3 name:
CH3CH
Cl in which
Br
acids
a formate
carboxyl
group
is potassium
attached toacetate
a ring are
2CHCH2
me3lo Carboxylic

nam
g-lactones,
d-lactones.
ring lactones aresystematic
six-membered
ring
lactones arebromide
name: and
ethanoyl
chloride
3-methylpentanoyl
cyclopentanecarbonyl
carboxylic
acid
to the -methylvaleryl
namefollowed
of the
cyclic compound.
common
acetyl
chloride
bromide
chloride
Salts of carboxylic acids are named in the
samename:
way. The
cation
is named
first,
esters are called lactones.OIn systematic nomencl
by the name of the acid,Oagain with ic acid
ate. O
Molecules:
O replaced byCyclic
O
prolactone;
2-oxacycloalkanones.
Their common names are derived from
Acid O
Anhydrides
O
COOH
O O
O
EthylcyclohexaneO
Loss of water from
two molecules
of a carboxylic
acid results inthe
anOacid
anhydride.
C acid,
carboxylic
which
designates
length
of the carbon ch
oxamide
Anhydride means without water.
OH
C
C
CH C
H

O Na+

2-oxacyclopentanone
2-oxaciclopentanona
-butyrolactone
-bu3rolactona
ematic name: sodium methanoate
ommon name:
sodium formate

indicate the carbon3 to which

the carboxyl
CH2CH3 oxygen is attached. T

+
O
Na
O
O
O 3-e3l-2-oxaciclopentanona
O
2-oxacyclohexanone
3-methyl-2-oxacyclohexanone
3-ethyl-2-oxacyclopentanone
are b-lactones
(the
carboxyl
oxygen is on the b
2-oxaciclohexanona lactones
3-me3l-2-oxaciclohexanona
-valerolactone
-caprolactone
-caprolactone
-valerolactona ring Clactones
-caprolactona
-caprolactona
CH3
C andCsix-membered
areC g-lactones,
ring lactones a
potassium ethanoate
sodium
R
OH
HO benzenecarboxylate
R
R
O
R
CH3

O K+

cyclohexanecarboxylic acid
trans-3-methylcyclopentanecarboxylic
potassium acetate
sodium benzoate
an acid anhydride
acid

PROBLEM 1
3-D Molecules:

1,2,

COOH

COOH

OH

Carbonyl Compounds I

Anhdridos de cido

cyclohexanecarboxylic acid

CH3

trans-3-methylcyclopentanecarboxylic
C
C acid
C

CH3
systematic name:
Acyl Halides
common name:

CH3

CH3

ethanoic anhydride

COOH

O
O

1,2,4-benzenetricarboxylic
acid
C

ethanoic methanoic anhydride

anhdrido
etanoico
anhdrido
etanoico
metanoico
acetic anhydride
acetic formic
anhydride
mixeda
anhydride
anhdrido
c3co
Acyl halides are compoundsa symmetrical
that
have aanhydride
halogen atomanhdrido
in aplace
of
the OH
group of a
c3co
frmico

carboxylic
acid. The most common acyl halides are acyl chlorides and acyl bromides.
Esters
Acyl halides
by using
theanacid
replacing
icgroup
acidofwith
yl chloOR name
An esterare
is anamed
compound
that has
group and
in place
of the OH
a carboxylic
ride (or
yl
For the
acids
ending
acidisis
(R) attachedacid,
acid.
In bromide).
naming an ester,
name
of thewith
groupcarboxylic
to thecarboxylic
carboxyl oxygen
replaced
with
carbonyl chloride (or bromide).
stated
Haluros
de first,
acilofollowed by the name of the acid, with ic acid replaced by ate.
O

carbonyl oxygen

CH3

Cl

systematic name: ethanoyl chloride

common name: cloruro
acetyl
chloride
de
etanoilo

Acid AnhydridesC
OCH2CH3

CH3CH2

CH3
CH
OR
3CH2CHCH2

me3lpentanoilo

CH3CHCH2

cyclopentanecarbonyl
cloruro de
chloride

O
C

Cl

Br

3-methylpentanoyl bromide
bromuro
e 3-
carboxyl
oxygendbromide
-methylvaleryl

Br
O

OCH3

ciclopentanoilo

OCH CH

2
3
Loss of water from two molecules of a carboxylic acid results in an acid anhydride.
Anhydride means without water.

thyl ethanoate
ethyl acetate

phenyl propanoate
phenyl propionate
O

methyl 3-bromobutanoate
methyl
O -bromobutyrate
O

ethyl cyclohexanecarboxylate

3-D
tran
pen
Acet

O
C

systematic name: ethanamide

common name: acetamide

benzenecarboxamide
cis-2-ethylcyclohexa
4-chlorobutanamide
benzamide
-chlorobutyramideSection 17.1
Nomenclature
675

CH3CH2CH2
NC
CH3CH
NCH
2CH
2CH2 the name
2CH
3
If a substituent is bonded
to the
nitrogen,
of the
substituent
is stated
first
e has an NH 2 , NHR, or NR
groupisinmore
place
of one
the substituent
OH group of
a carboxylic
(if2 there
than
bonded
to the nitrogen, they are stated alphabetCH
CHof3each substituent is preceded
des are
named by using theically),
acid name,
replacing
oic acid
ic acid
followed
by the name
of theoramide.
The with
name
Amidas
N-cyclohexylpropanamide
by a capital
N to
indicate
that
the substituent
is bonded to a nitrogen.
For acids ending
with carboxylic
acid,
ylic
acidN-ethyl-N-methylpentanamide
is replaced
with amide.
N,N-diethylbutanam
CH3CH2

NH

Cyclic
amides are called
is similar
to that
C of lactones.
C
C
C
C nomenclature
C
C lactams. Their
CH
CH
CH
NCH2CH3
CH32CH
NH2CH
CH3CH2CH
NCH2CH3
CH3
ClCH
3 NH
2 2 2
22CH2 NH NH2
2
2
They
areNHnamed
asCH
2-azacycloalkanones
in 2systematic
nomenclature
(aza
is used
CH
CH
CH
2
3
3
CH
2CH3
to designate the nitrogen
atom).
In
their
common
names,
the
length
of
the
carbon
N-cyclohexylpropanamidebenzenecarboxamide
N-ethyl-N-methylpentanamide
N,N-diethylbutanamide
etanamida
4-clorobutanamida
cis-2-ethylcyclohexanecarboxamide
name: ethanamide
4-chlorobutanamide
N-e3l-N-me3lpentanamida
N,N-die3lbutanamida
chain
is
indicated
by
the
common
name
of
the
carboxylic
acid,
and
a Greek letter indibenzamide
name: acetamide
-chlorobutyramide
cates the carbon to
which
the
is attached.
Cyclic
amides
arenitrogen
called lactams.
Their nomenclature is similar to that of lactones.

They are named

as 2-azacycloalkanones
in systematic
nomenclature (aza is used
bstituent is bonded to the nitrogen,
the name
of the substituent is stated
first
tobonded
designate
the nitrogen,
nitrogen atom).
In stated
their common
s more than one substituent
to the
they are
alphabet-names, the length of the carbon
O
is indicated
byof
theeach
common
name ofisthe
carboxylic acid, and a Greek letter indillowed by the name of thechain
amide.
The name
substituent
preceded
O
cates the carbon
to which
the nitrogen is attached.
O
al N to indicate that the substituent
is bonded
to a nitrogen.

NH

O
NH

hexylpropanamide

O
NH

NHO

NH

C
NH
NH
CH
CH
CH
NCH2-azacyclobutanone
CH
NCH2CH
3
2
2
2CH3
3CH2CH2CH2
32-azaciclopentanona
2-azacyclohexanone
2-azacyclopentanone
2-azaciclohexanona
2-azaciclobutanona
C

-valerolactam
-butyrolactam
-valerolactama
-bu3rolactama
-propiolactama
2-azacyclohexanone
2-azacyclopentanoneCH2-azacyclobutanone
CH3
2CH3-propiolactam

-valerolactam
N-ethyl-N-methylpentanamide

-butyrolactam
-propiolactam
N,N-diethylbutanamide

amides
are called lactams.Nitriles
Their nomenclature is similar to that of lactones.
Nitriles
N functional
Nitriles in
aresystematic
compoundsnomenclature
that contain a C
3-D M
named as 2-azacycloalkanones
(aza
is used group. Nitriles are considered
C

N
Nitriles
are
compounds
that
contain
a
functional
group.
Nitriles
are
considered
Aceto
acid derivatives
because,
all Class
I carbonyl compounds, they react
ate the nitrogen atom). Incarboxylic
their common
names, the
lengthlike
of the
carbon

on of the nitrile group is counted in the number of carbons in the longest

12.10
Thiols, Sulfides,
andbySulfonium
Salts
chain. In
common nomenclature,
nitriles are named
replacing ic acid
oxylic acid name with onitrile. They can also be named as alkyl
are
analogs
of alcohols.
be called mercaptans because
tating Thiols
the name
of sulfur
the alkyl
group that
is attachedThiols
to the Cused
group.
Nto

me:
me:

Nitrilos
they form strong complexes with heavy metal cations such as mercury and arsenic
(they capture mercury).
CH3
CH3C

2 CH3CH2SH +

2+

Hg

ethanenitrile
benzenecarbonitrile
mercuric ion
etanonitrilo a thiol
bencenocarbononitrilo
acetonitrile
benzonitrile
acetonitrilo
benzonitrilo
methyl cyanide
phenyl cyanide

cianuro
de mare
e3lonamed
cianuro
de fenilothe
Thiols
by adding

CH3CHCH2CH2CH2C

CH3CH2S

Hg

CH2

CHC
+

SCH2CH3 + 2 H

5-methylhexanenitrile
5-me3lhexanonitrilo
-methylcapronitrile
-me3lcapronitrilo
isohexyl cyanide

propenenitrile
propenonitrilo
acrylonitrile

acrilonitrilo

cianuro to
de the
isohexilo
suffix thiol
name of the parent hydrocarbon. If there is a second functional group in the molecule, the SH group can be
indicated by its substituent name, mercapto. Like other substituent names, it is cited
Mercaptanos
(3oles)
before the name
of the parent hydrocarbon.

CH3
CH3CH2SH
ethanethiol
etano3ol

CH3CH2CH2SH
1-propanethiol
1-propano3ol

CH3CHCH2CH2SH

3-methyl-1-butanethiol
3-me3l-1-butano3ol

HSCH2CH2OH

2-mercaptoethanol
2-mercaptoetanol

Low-molecular-weight thiols are noted for their strong and pungent odors, such as
those associated with onions, garlic, and skunks. Natural gas is completely odorless
and can cause deadly explosions if a leak goes undetected. Therefore, a small amount
of a thiol is added to natural gas to give it an odor so that gas leaks can be detected.
Sulfur is larger than oxygen, so the negative charge of the thiolate ion is spread over a
larger volume of space, causing it to be more stable than an alkoxide ion. Recall that the

Isomera

Ismeros
Ismeros
Cons3tucionales
(cadena, posicin, funcin)

Estereoismeros

Geomtricos
(cis, trans)

p3cos

enan3meros

diasteroismeros

ompounds that have the same

ethanol is bonded to a carbon and to a hydro
molecular formula but are not
is bonded to two carbons.
identical are called isomers.
somers
fall into
two main classes:
Ismeros
cons3tucionales
constitutional isomers and stereoconstitutional isomers
somers.
Constitutional
isomersemprica,
differ pero dieren entre s en el orden en que
Poseen
la misma frmula
n the way their atoms are connected
CH3CH2OH
and
CH3OCH3
estn
e
nlazados
l
os

tomos
e
n
l
a
m
olcula
ethanol
Section 2.0). For example, ethanol and
nonsuperimposable dimethyl ether
mirror images
dimethyl ether are constitutional isomers
CH3
because they have the same molecular formula,
Dieren en el arreglo
C2HCadena:
are3CH
connected
in 3
CH3oxygen
CHCH2CH
6O, but the atoms in each compound CH
2CH2CHdifferently.
2CH3 and The
de la
adena dto
e caarbonos
ethanol
iscbonded
carbon and to a hydrogen, whereas
ether
pentanethe oxygen in dimethyl
isopentane
pentano
isopentano
s bonded to two carbons.

utional isomers

Posicin:
Dieren
el 3OCH3
H3CH
and en
CH
2OH

posicin de un grupo
funcional
ethanol
dimethyl
ether
CH3

H2CH2CH2CH3 and CH3CHCH2CH3

pentane

182

isopentane

Unlike the atoms in constitutional isom

Cl
nected in the same way. Stereoisomers
(al
atoms
CH3are
CH2arranged
CHCH3 in spac
CH3in
CHthe
Cl and
2CHway
2CH2their
1-chlorobutane
that do not readily 2-chlorobutane
interconvert. Therefor
1-clorobutano
2-clorobutano
kindsO of stereoisomers: cistrans
isom
O
(ky-RAL-i-tee) centers.
CH3CCH3
acetone

and

CH3CH2CH

propionaldehyde

mirror
onstitutional isomers
C2H 6O,
butimages
the atoms in each compound are connected d
he same molecular formula,
ethanol is bonded to a carbon and to a hydrogen, whereas th
in each compound are connected
The oxygen in
is bondeddifferently.
to two carbons.
carbon and to a hydrogen, whereas the oxygen in dimethyl ether
ns.Funcin: Poseen diferente grupo funcional

constitutional isomers

CH3CH2OH
CH3OCH3

imethyl ether

CH3

H3CHCH2CH3
isopentane

and

ethanol
etanol

CH3Cl
OCH3

dimethyl
dimetll ether
ter

CH3CH2CH2CH2Cl and CH3CH2CHCH3

CH3
2-chlorobutane
1-chlorobutane

CH3CH2CH
O2CH2CH3 and CH3CHCH
O2CH3
pentane

CH3CCH3
acetone
acetona

and

isopentane

CH3CH2CH

CH3CH2CH2CH

1-chlorobutan

CH3CCH3
acetone

propionaldehyde
propanaldehdo

Unlike the atoms in constitutional isomers, the atoms

nected in the same way. Stereoisomers (also called config
n constitutional isomers, the atoms in stereoisomers are conin the way their atoms are arranged in space. Stereoisomer
y. Stereoisomers (also called configurational isomers) differ
that do not readily interconvert. Therefore, they can be
are arranged in space. Stereoisomers are different compounds
of separated.
stereoisomers:
terconvert. Therefore, theykinds
can be
There cistrans
are two isomers and isome
(ky-RAL-i-tee)
rs: cistrans isomers and
isomers thatcenters.
contain chirality

s.

a. Draw
three constitutional
isomers
with molecular
(Section 3.4). Restricted rotation can be caused
either
by a double
bond
or by aformula
cyclicC3H 8O.
b. How
manyaconstitutional
isomers can
you drawbond,
for C4H 10
O?
structure. As a result of the restricted rotation
about
carboncarbon
double
an
such rotation
as 2-pentene can exist as cis and trans isomers. The cis isomer has the hyetric isomers) result fromalkene
restricted
same side of the double bond, whereas the trans isomer has the
e caused either by a doubledrogens
bond or on
by athe
cyclic
5.1 CisTrans Isomers
Ismeros
g
eomtricos
(
cis-trans)
hydrogens
on opposite
sides of the double bond.
otation about a carboncarbon
double bond,
an

s and trans isomers. The cis isomer has the hyCistrans isomers (also called geometric isomers) result from restricted rot
(Section 3.4). Restricted rotation can be caused either by a double bond or by a c
ble bond, whereas the trans isomer has the
Resultan de la rotacin restringida de una molcula. La restriccin puede
structure. As a result of the restricted rotation about a carboncarbon double bon
ble bond.
alkene such as 2-pentene can exist as cis and trans isomers. The cis isomer has th

ser consecuencia de un doble enlace o de udrogens

n estructura
cclica
on the same side
of the double bond, whereas the trans isomer ha
hydrogens on opposite sides of the double bond.

CH2CH3

H3C
C
CH2CH3

H3C
C
H

trans-2-pentene

CH2C
CH
H3C
2CH3
trans-2-pentene
H

cis-2-pentene
trans-2-pentene
C cis-2-pentene
C C
CHhave
H can also
H compounds
2CH3cis and trans isomers (Section 2.14). The cis isoCyclic

cis-2-pentene

2-pentene

H 3C

H3C

3-D M
cis-2Cyclic compounds can also have cis and trans isomers (Section 2.14). The
cis

mer has the hydrogens

on the same side ofcis-2-penteno
the ring, whereas the
trans isomer has the
cis-2-penteno
trans-2-penteno
trans-2-penteno
cis-2-pentene

trans-2-pentene

cis-2-pentene

hydrogens
sides of the ring.
s and trans isomers (Section
2.14). Theon
cisopposite
iso3-D Molecules: mer has the hydrogens on the same side of the ring, whereas the trans isomer ha
de of the ring, whereas the trans isomer has the
hydrogens on opposite sides of
H cis-2-Pentene; trans-2-Pentene
Brthe ring.
g.
H
Br
H
H
Br

Br

cis-1-bromo-3-chlorocyclobutane
cis-1-bromo-3-lorociclobutano

Cl

trans-1-bromo-3-chlorocyclobutane

CH3

CH3

cis-1,4-dimethylcyclohexane
cis-1,4-dime3lciclohexano

trans-1,4-dimethylcyclohexane

PROBLEM 2

Br

Cl

cis-1-bromo-3-chlorocyclobutane

trans-1-bromo-3-chlorocyclobutane

trans-1-bromo-3-chlorocyclobutane
trans-1-bromo-3-lorociclobutano

CH3

H3C

H3C
H3C

ClCl

Cl

CH3

cis-1,4-dimethylcyclohexane

H3C

H
H3C

CH3
H

trans-1,4-dimethylcyclohexane

trans-1,4-dimethylcyclohexane
PROBLEM
2
trans-1,4-dime3lciclohexano
Draw the cis and trans isomers for the following compounds:
a. 1-ethyl-3-methylcyclobutane
c. 1-bromo-4-chlorocyclohexane
b. 2-methyl-3-heptene
d. 1,3-dibromocyclobutane

he
E,Z
System
Nomenclature
same,
the
atoms
attached
to the
CH(CH
so there is a tie at this point. The C of the CH 2O
arbon
is bonded
to a Cl of
and
to a C. Cl has the
greater3)atomic
number,
2 group),

d
atomspriority
are compared;
one that you use the atomic number of C,
2 than C.the
aach
higher
(Notice
bonded to O, H, and H, and the C of the CH(CH 3)2 group is bonded to
of
the
carbons
of
sp
h the greatest atomic number an alkene is bonded to only one substituent, we
ass of the CH 3 group, because the prioritiesH.
areOf
based
theatoms,
atomicO has the greatest atomic number, so CH 2OH
theseonsix
erms
cistheand
trans
tothe
designate
ongs to
group
with
higher the structure of the alkene. If the hydrogens
f atoms, not on the masses of groups.) The isomer
on the
leftCH(CH
has the 3)2 . (Note that you do not add the atomic num
erisomer;
priority
than
ority. side of the double bond, it is the cis
ame
if
they
are on opposite
ty groups
(Br and Cl) on the
same
side of thetake
double
bond,
soatom
it is the
Nomenclatura
E

-

Z
the
single
with the
the isogreatest atomic number.) The E and Z i
double
bond,are
it is
Butisomer
how would
you
designate
(Zee groups
onthe
Zeetrans
Zameisomer.
Zide.) The
on
the
right
has
the
as shown.
mpound
as 1-bromo-2-chloropropene?
ty groupssuch
on opposite
sides of the double bond, so it is the E isomer.
Rule
3. Ifthe
ansame
atomatom
is doubly bonded to another atom, the priority sy
the two substituents
start
with
Cl to an sp 2 carbon
CH
Br bonded
Br
3
it as
if it wereand
singly
bonded to two of those atoms. If an atom is triply
tie), you must move outward from the point of
attachment
considC C
C C
Cul
es csystem
is o ctreats
ul iteas
s tifrans?
atom,
the priority
it were singly bonded
mic numbers of the atoms that are attached toanother
the tied
atoms.
those
atoms.both to a Cl
H
H
ollowing compounds,
oneCH
of3 the sp 2 carbons
isCl
bonded
For example, one of the sp 2 carbons in the following pair of isome
C of a CH 2Cl group:
Which isomer is cis and which is trans?

ed to a CH 2CH 3 group and to a CH CH 2 group:

CH3
CH3the cistrans system of nomenpound such as 1-bromo-2-chloropropene,

CH2CH3
CH CH2
HOCH2
2
ot be used
because
there3 are four
substituents
onHOCH
the two
vinylic
CHCH
ClCH
CHCH
Cl different
2
3
E,Z systemCof Cnomenclature wasC devised
for these kinds of C
situations.*
C C
C
C
an isomer by the E,Z system, we first determine the relative priorities of
HC C
CH CH2
HC C
CH2CH3
OH 2 ClCH2
CHthen
2OH the relative priorities of the
sp carbons and
ps bondedClto one CH
of 2the
the
Z isomer
the Erules
isomer
spZ2 carbon. (The
bonded to the
other
the
Zpriorities
isomer
the E isomer
Ismero
Ismero
E for assigning relative
Ismero
Z
Ismero
E
d next.) If the high-priority groups are on the same side of the double
reater
atomic
number
C, so(Zthe
has the German
higher
priority.
has
the Z
configuration
is Cl
forgroup
zusammen,
for
together).bonded to the sp 2 carbon are both Cs
nmer
atom
is doubly
bondedthan
to another
Because
the
atoms
immediately
2
Regla
1it: are
N
mero
abonded
tmico
m
ayor,
ayor
egroup
s carbon
la
pand
rioridad
spopposite
CH
sm,bonded
other
carbon
are
Cs
am
an thehas
2OH
treat
it to
as the
if
were
riority
groups
onsingly
sides
of(from
thetie.
double
bond,
the
isomer
CHthe
The
first
of
group
is bonded
to C, H, and H
Z isomer
has the high-priority
2CH 3The
CH
OH
group),
so
there
is
a
tie
at
this
point.
The
C
of
the
group
is
wo
of
those
atoms.
2
groups onto
the
side. doubly bond
ion (E
is for2entgegen,
for opposite).
CH
CH 2 ugroup
carboneof
the
is
bonded
ansame
H sand
Regla
: Si the
dos
sGerman
us-tuyentes
p
oseen
l
m
ismo
tomo
nido
a
l
d
oble
e
nlace,
e
CH(CH
)
O,
H,
and
H,
and
C
of
the
group
is
bonded
to
C,
C,
and
3 2
n atom is triply bonded to another
itsiguiente
is considered
tocbe
bonded to C, C, and H. One C canc
low
priority
CH 2OH
em,
six
atoms,
greatest
atomic
number,
has
a high-en la
considera
ethe
l priority
nsingly
mero
atmico
dTherefore,
el sotomo
adena.
high
priority
low
priority
treat
it as O
if ithas
were
bonded
of
the
two numbers;
groups, leaving
H and H in the CH 2CH 3 group and C an
CH(CH
)
.
than of
(Note
that
you
do
not
add
the
atomic
you
3
2
hree
those
atoms.
C 3C: Si el sus-tuyente posee un
Regla
dand
oble
enlace, has
se caonsidera
que enumber
l tomo
est
nido
C
C 2Z group.
CH
greater atomic
than
H,uso
ngle atom with the greatest atomic number.)CH
The
E CH
isomersCare
ncel
atoms
that
are
identical
in the
priority
a dos
tomos
mediante
ehigh
nlaces
simples.
high
priority
higher
priority
than CH 2CH 3 . Both atoms that are bonded to the oth
priority
low priority
o groups; use the remaining atoms to
are Cs,system
so there
is a tie there as well. The triple-bonded C is co
an atom
doubly
bonded
to another atom, bon
the priority
treats
ermine
theisgroup
with
the higher
the
Z
isomer
the
E
isomer
bonded
to bonded
C, C, and
ere singly bonded to two of those atoms. If anbeatom
is triply
to C; the other C is bonded to O, H, and H.
ority.

5.2

Chirality

Why cant you put your right shoe on your left foot? Why cant you put your right
glove on your left hand? It is because hands, feet, gloves, and shoes have right-handed
and left-handed forms. An object with a right-handed and a left-handed form is said to
be chiral (ky-ral). Chiral comes from the Greek word cheir, which means hand.
Notice that chirality is a property of an entire object.
A chiral object has a nonsuperimposable mirror image. In other words, its mirror
image is not the same as itself. A hand is chiral because if you look at your left hand in
a mirror, you do not see your left hand; you see your right hand (Figure 5.1). In contrast, a chair is not chiralit looks the same in the mirror. Objects that are not chiral
are said to be achiral. An achiral object has a superimposable mirror image. Some
other achiral objects would be a table, a fork, and a glass.

Quiralidad

Quiral: Posee una imagen especular NO superponible

Aquiral: Posee una imagen especular superponible

PROBLEM 3

a. Name five capital letters that are chiral.

b. Name five capital letters that are achiral.

t for chirality. A
e same as its
are
An achiral
its mirror
erimposable.

ymmetric carbon

right hand

5.3

left hand

Asymmetric Carbons, Chirality Centers,

and Stereocenters

Not only can objects be chiral, molecules can be chiral, too. The feature that most
often is the cause of chirality in a molecule is an asymmetric carbon. (Other features
that cause chirality are relatively uncommon and are beyond the scope of this book.
You can, however, see one of these in Problem 88.)
An asymmetric carbon is a carbon atom that is bonded to four different groups. The
asymmetric carbon in each of the following compounds is indicated by an asterisk. For
example, the starred carbon in 4-octanol is an asymmetric carbon because it is bonded to
four different groups (H, OH, CH 2CH 2CH 3 , and CH 2CH 2CH 2CH 3). Notice that the
difference in the groups bonded to the asymmetric carbon is not necessarily right next to
the asymmetric carbon. For example, the propyl and butyl groups are different even
though the point at which they differ is somewhat removed from the asymmetric carbon.

Not only can objects be chiral, molecules can be chiral, too. The feature that most
often is the cause of chirality in a molecule is an asymmetric carbon. (Other features
that cause chirality are relatively uncommon and are beyond the scope of this book.
You
can, however,
see onequirales
of these in Problem 88.)
Molculas
orgnicas
An asymmetric carbon is a carbon atom that is bonded to four different groups. The
asymmetric carbon in each of the following compounds is indicated by an asterisk. For
De la misma
forma
que objetos
co-dianos
quirales carbon because it is bonded to
example,
the starred
carbon
in 4-octanol
is anson
asymmetric
las different
molculas
tambin
ser qCH
uirales
o aquirales.
four
groups
(H,pueden
OH, CH
2
2CH 3 , and CH 2CH 2CH 2CH 3). Notice that the
La causa inprincipal
de bonded
quiralidad
en una
molcula carbon
es la is not necessarily right next to
difference
the groups
to the
asymmetric
de un
centro For
estereognico
o asimtrico
que
thepresencia
asymmetric
carbon.
example, the
propyl and
butyl groups are different even
corresponde
unido
a cuatro
sus3tuyentes
though
the pointun
at carbono
which they
differ
is somewhat
removed from the asymmetric carbon.
Thediferentes
starred carbon in 2,4-dimethylhexane is an asymmetric carbon because it is bonded
to four different groupsmethyl, ethyl, isobutyl, and hydrogen.
CH3
*

CH3CH2CH2CHCH2CH2CH2CH3
OH
4-octanol
4-octanol

CH3CHCH2CH3
Br
2-bromobutane
2-bromobutano

CH3CHCH2CHCH2CH3
CH3
2,4-dimethylhexane
2,4-dime3lhexano

Mo3vacin

La Tercera - 17/10/2011

CH3

CH3

the two isomers of 2-bromobutane

enantiomers

Enan3meros
Take a break and convince yourself that the two 2-bromobutane isomers are not identical, by building ball-and-stick models using four different-colored balls to represent the
four different groups bonded to the asymmetric carbon. Try to superimpose them.
Nonsuperimposable
moleculesno
areson
called enantiomers (from the
La molculas
que su mirror-image
imagen especular
Greek enantion,
which means enan3meros.
opposite). The Como
two stereoisomers of 2-bromobusuperponibles
se denominan
tane are enantiomers. A molecule that has a nonsuperimposable mirror image, like
consecuencia,
los enan-meros son molculas
an object that has a nonsuperimposable mirror image, is chiral. Each of the
quirales.
La quiralidad
es una that
propiedad
de la
enantiomers
is chiral. A molecule
has a superimposable
mirror image, like an
molculas
completa.
object that
has a superimposable mirror image, is achiral. To see that the achiral
moleule is superimposable on its mirror image (i.e., they are identical molecules),
mentally rotate the achiral molecule clockwise. Notice that chirality is a property of
the entire molecule.

impos-

mpos-

mirror

Br
C
CH3CH2

H
CH3

Br
H
H3C

Br
CH2CH3

a chiral
nonsuperimposable
molecule
imageno
quiral mirror
(imagen
enantiomers
superponible)

PROBLEM 6

C
CH3CH2

CH3
CH3

Br
H3C
H3C

CH2CH3

an achiral
superimposable
molecule aquiral
mirror
image
(imagen
identical
molecules
superponible)

Representacin de enan3meros
Frmulas en perspec3va o cuas

Se

Br

Br
H

CH3
CH2CH3

C
H
H3C
CH3CH2

2-bromobutano
perspective formulas of the enantiomers of 2-bromobutane

Proyecciones de Fischer

A shortcutcalled a Fischer projectionfor showing the three-dimensi

arrangement of groups bonded to an asymmetric carbon was devised in the late 18
H
H
by Emil CH
Fischer.
A Fischer projecton
represents an asymmetric carbon
as the poin
2CH3
intersection
of two perpendicular
lines;
horizontal linesCHrepresent
theOH
bonds that
C
OH
H3C-H2C
3CH2
C
H
ject out
the plane of the paper toward
the viewer, and verticalCHlines represent
H3C of OH
CH3
3
bonds2-butanol
that extend back from the plane of the paper away from the viewer. The car
Proyecciones
chain always is drawn vertically with C-1 at the top of the chain.
de Fischer

CH3

asymmetric carbon

CH3

S
System
Nomenclature
vakia.
He taughtof
at the

1. Rank the groups (or atoms) bonded to the asymmetric carbon in order of
of Zagreb from 1935 until
has the lowest priority
priority.
atomic such
numbers
of the atoms directly attached to the asymmetricthis
carbon
ame
the individual
stereoisomers
of aThe
compound
as 2-bromon he fled
to Switzerland
relative
priorities.
The
now
stereoisomer
are talkingthe
about.
In other
words,
wehigher the atomic number, the higher the priority.
of thewhich
invading
German wedetermine
Orient the
so that
The molecule
is oriented
so the
theofgroup
(This
should
remind
you of
way
aremolecule
determined
for the
the group
E,Z (or atom) wit
was
a professor
at the
menclature
that
indicates the
configuration
(arrangement)
the relative 2.priorities
the lowest priority
points the
away
away was
fromoriginally
you. Thendevised
draw anfor
imaginary
arrow from
ral the
Institute
of Technology
systemwith
ofuse
nomenclature
system rected
of priorities
the
out
asymmetric
carbon. Chemists
the letters Rbecause
and
S to
infrom
the
viewer.
If
an
arrow
drawn
from
rtion
his about
work that
contributed carbon.
highest priority
(1) to
the group
R,S system
of pair
nomenclature
and was
later borrowed
for the E,Z
system.
You (or
mayatom)
wantwith the next hi
anecesario
asymmetric
For
any
of enantiomers
with
the highest
priority
groupdto
the
next
Es
n

e
stablecer
u
n
s
istema
e
n
omenclatura
d
e
t
al
m
anera
d
e
d
iferenciar
los
rstanding
of how
living
points
clockwise,
asymmetric
carbon
to revisit
Section
towill
review
how
priorities
are the
determined
before
youhas the R config
bon,
one will
have
the orR configuration
and
the 3.5
other
have
the relative
highest
priority
group
points
clockwise,
arryR,S
outenan-meros.
chemical
reacLatin Cahn,
for right).
If the arrow
points permite
counterclockwis
La
conguracin
R-S
propuesto is por
Ingold
y Prelog
proceed
with
theand
R,S
system.
he
system
was
devised by
Cahn,
Ingold,
the
molecule
hasPrelog.
the
R configuration.
hared the 1975 Nobel Prize
the S configuration (S is for sinister, which is Latin for le
t how we can determine
the configuration of a compound if we
ry with diferenciar
John Cornforth enan-meros
this has the highest priority
ional
model of the compound.
.
clockwise = R configu

Nomenclatura enan3meros

2
4

3
2

Enan3mero R

ups (or atoms) bonded to the asymmetric carbon in order

thisofhas the lowest priority
numbers
of the
directly attached
to the
carbon
Paso
1: atoms
Establecer
el orden
de asymmetric
prioridad
de los sus-tuyentes basado en el nmero
ve
priorities.
The
higher
the
atomic
number,
the
higher
the
priority.
2. Orient the molecule so that the group (or atom) with the lowest priority (4) is dile is oriented so the group
atmico.
(relative
U-lizar
l
as misma
ryou.
eglas
pdraw
ara
a E,Z
nimaginary
omenclatura
Z - E)
d you
of the
way
priorities
arefrom
determined
thelan
west
priority
points
away
rected away
Thenfor
arrow from the group (or atom) with the
ewer.
If Paso
an arrow
fromof priorities
ture because
the
was originally
for
2drawn
: system
Orientar
la molcuas
tdevised
al group
manera
que
el the
sus-tuyente
de m(2).
enor
rioridad sea
highest
priority
(1)dtoe the
(or the
atom)
with
next highest priority
If theparrow
priority
group
to
the
next
nclature and was later borrowed
for
the
E,Z
system.
You
may
want
points clockwise, the asymmetric carbon has the R configuration (R is for rectus, which
m
s
alejado.
ority group
points
clockwise,
.5 to el
review
how
relative is
priorities
determined
you counterclockwise, the asymmetric carbon has
Latin forare
right).
If the before
arrow points
e has the R configuration.
S system.
Paso 3: Unir mediante
una echa
los sinister,
sus-tuyentes
(los
de ms alta prioridad), si la
the S configuration
(S is for
which is Latin
for3left).

echa
gira en el sen-do del reloj corresponde
al enanimero R, por el contrario si la
this has the highest priority
clockwise = R configuration
echa gira en sen-do an-horario corresponde
al enan-mero S.
1
1

1. Rank the groups (or atoms) that are bonded to the asymmetric carbon in order of
priority. In the following pair of enantiomers, bromine has the highest priority (1), the
ethyl group has the second highest priority (2), the methyl group is next (3), and hydrogen has the lowest priority (4). (Revisit Section 3.5 if you dont understand how
Nomenclatura
nan3meros
these priorities e
are
assigned.)
1

Br

Br
CH3CH2
2

H
CH3

CH3

(S)-2-bromobutano

CH2CH3
2

(R)-2-bromobutano

2. If the group
(or
atom) with d
the
Conguracin
R-S en
proyecciones
e Flowest
ischer priority is bonded by a hatched wedge,
draw an arrow from the group (or atom) with the highest priority (1) to the group (or
atom) with the second highest priority (2). If the arrow points clockwise, the compound has the R configuration, and if it4 points counterclockwise, the compound has
H
H
CH2CH3
the S configuration.
H
C
H
H3C
OH

2-butanol

CH3CH2
2

OH 1
2 CH3CH2
C
OH
1 H3C-H2C
1
CH3
Br
Br
CH
3
3
C H4
C
4

CH3
3

(S)-2-bromobutane

CH3

OH 1

2 CH3CH2

CH3

CH2CH3
2

Configuracin S

(S)-2-butanol

(R)-2-bromobutane

3. If the group with the lowest priority (4) is NOT bonded by a hatched wedge,

Clockwis
ity subst

tiomer has the R configuration; if it points counterclockwise, the enantiomer has the S
configuration,
provided
that the group
with the lowest
(4) drawn
is on aasvertical
bond.
Now lets see
how to determine
the configuration
of apriority
compound
a Fischer

4. In drawing the arrow from group 1 to group 2, you can draw past the group with the
projection.
1
1
lowest priority (4), but never
draw past the group with the next lowest
priority (3).
Cl
Cl
1. Rank the groups (or atoms)
carbon in order of
1 that are bonded to the asymmetric
1
Otros ejemplosCH3CH2
CH
CH
CH
CH
CH
CH
CH2CH3
2
2
3
3 OH
2
2
OH
priority.
2
2
3
3
H4
H4
C
C
4
4
2. Draw an arrow from the group
H(or atom) with the highestHpriority (1) to the group
CHhighest
CH3arrow
CH(S)-3-chlorohexane
3CH2
2 points clockwise, the enan(R)-3-chlorohexane
(or atom) with the next
priority
(2). If the
CH2CH2Br
CH2CH2Br
3
3
2
2
tiomer has the R configuration; if it points counterclockwise,
the enantiomer has the S
(R)-1-bromo-3-pentanol
3.
If the groupprovided
(or (R)-1-bromo-3-pentanol
atom)
the lowest
priority
on a horizontal
the
answer
configuration,
thatwith
the group
with the
lowestispriority
(4) is on a bond,
vertical
bond.

you get from the direction of1 the arrow will be the opposite of1 the correct answer. For
Now lets see how to determine the configuration of a compound drawn as a Fischer
example,
if the arrow points Cl
clockwise, suggesting that the asymmetric
carbon has the
Cl
projection.
R configuration, it actually
the2CH
S 2configuration;
if the
points
CH3CH2 hasCH
CH3
CH3CH
CH
2CHarrow
2
2CH3 counterclock2
2
3
1. Rank that
the groups
(or
are bonded
asymmetric
carbon
in order
H 4atoms) that
H4
wise, suggesting
the3 asymmetric
carbon
has thetoSthe
configuration,
it actually
hasofthe
priority.
R configuration.
In the (R)-3-chlorohexane
following example, the group
with the lowest priority is on a
(S)-3-chlorohexane
(R)-3-clorohexano
Drawso
an clockwise
arrow
from signifies
the group the
(or atom)
with(S)-3-clorohexano
the highest
(1) to the group
horizontal2.bond,
S configuration,
not priority
the R configuration.

(orIfatom)
with (or
theatom)
next highest
(2). If the
arrow
points clockwise,
enan3.
the group
with 3thepriority
lowest priority
is on
a horizontal
bond, the the
answer
3
hasthe
the direction
R configuration;
if it points
counterclockwise,
the correct
enantiomer
has For
the S
youtiomer
get from
of theCH
arrow
will be
the opposite
of the
answer.
CH
3 1
3
1 priority (4) is on a vertical bond.
configuration,
provided
that
the groupsuggesting
with the lowest
example,
if the arrow
points
clockwise,
that
carbon has the
HO the asymmetric
4H
OH
H4
R configuration, it actually has1 the S configuration; if the arrow points
counterclock1
CH
CH
CH
CH
2 carbon
3
2
3 Cl it actually has the
Cl
wise, suggesting that the asymmetric
has the S configuration,
2
2
priorCH3following
CH(S)-2-butanol
CH
CHwith
CH2lowest
CHpriority
R configuration. In the
example,
is on a
2
2CH2CH3the group
3CH2the
2CH3
(R)-2-butanol
.
2
2
3
3 (S)-2-butanol
(R)-2-butanol
horizontal bond, so clockwise H
signifies
the S configuration, not theHR4 configuration.
4

4. In drawing the arrow

from group
1 to group 2, you
can draw past the group (or
(R)-3-chlorohexane
3
3(S)-3-chlorohexane
CH

CH

never rotateCH(CH
one 90) or turn one over, because this is a quick way to get a wrong an3 2
swer. A Fischer projection can be rotated 180 in the plane of the paper, but this is the
a. way toCmove it without risking an incorrectc.answer.
only
CH2CH3
CH3
HO
Ejercicios
CH2Br
PROBLEM 8
1. Indicar la conguracin
absoluta y nombre de los siguientes cCl
ompuestos
CHeach
2Br of the following structures has the R or the
Indicate whether
S configuration:
b.

d.

C ) CH CH Cl
CH(CH
3 2
2
2

CH3CH2

OH
b)c.
CH
CH
2
3
CH3
HO
CH2Br
PROBLEM 9 SOLVED
CH2Br compuestos son enan-meros. Cl
2. Indicar si los siguientes
a.
a)

Do the following structures represent identical molecules or a pair of enantiomers?

b.

d.

C CH CH Cl
2
2
CH3CH
2 3
CH
OH

OH

a)
a.

y
and
C H
C CH
3
HO
CH3CH2CH2 H
PROBLEMCH
92CH2SOLVED
CH3
Do the following structures represent identical molecules or a pair of enantiomers?

b
b.
)a.

CH2Br

CH3

Cl

Cl

y
and

OH

CH

3
and
C
H CH
CH3C CH
CH3CH2 CH BrCH3
2
3
HO
CH3CH2CH2 2H
CH2CH2CH3

CH2Br

CH2Br

Cl

Cl

CH3

light
source

normal
light

polarizer

plane-polarized
light

sample tube
containing a
chiral compound

plane-polarized
light

A compound that rotates the plane of polarization is said to be optically active. In Joseph
Achille5.7
Le BelOptical
(18471930
Section
Act
Ac3vidad
p3ca
other words, chiral
compounds are optically active and achiral compounds are a French chemist, inherited his fam
lys fortune, which enabled him to
optically inactive.
Plano
de of
luzpolarization
polarizado

establish
his
own laboratory. He a
If an optically active compound rotates the plane of polarization clockwise, it isthe plane
sin
rotacin
has
not
been
rotated
Direccin
propagacin
de larotates
luz the vant Hoff independently arrived a
direction
of
light compound
propagation
called dextrorotatory, indicated by (+). If an
opticallyde
active
plane of polarization counterclockwise, it is called levorotatory, indicated by (-). the reason for the optical activity o
certain molecules. Although vant
Dextro and levo are Latin prefixes for to the right and to the left, respectively.
Hoffs explanation was more preci
Sometimes lowercase d and l are used instead of (+) and (-).
both chemists are given credit for t
Do not confuse (+) and (-) with R and S. The (+) and (-) symbols indicate the di- work.
rection in which an optically active compound rotates the plane of polarization, whereas R and S indicate the arrangement of the groups about an asymmetric carbon. Some Some molecules with the R configura
compounds with the R configuration are (+) and some are (-).
tion are ("), and some molecules wit
the Rplane-polarized
configuration are (!).
The
degree
an optically
active compound
rotates
of polarization
light
normal
sample
tube
polarizer
plane-polarized
Polarizador
Fuente
de to which
Luz
Plano de
luz the plane
Muestra
de un
plano de luz
light
containing
an the
light
light
cansource
be
measured
with
an
instrument
called
a
polarimeter
(Figure
5.2).
Because
Luz
Normal
Polarizada
compuesto
aquiral
polarizada
Figure
5.2
achiral compound
Schematic of a polarimeter.

Direccin
deofpropagacin
luz compound, the
However, when polarized light passes
through
alight
solution
ofdealachiral
direction
propagation
light emerges with its plane of polarization changed. Thus, a chiral compound rotates
the plane of polarization. A chiral compound will rotate the plane of polarization
clockwise or counterclockwise. If one enantiomer rotates the plane of polarization
clockwise, its mirror image will rotate the plane of polarization exactly the same
amount counterclockwise.
light
Fuente
de
source

Luz

normal
Luz
light

Normal

polarizer

Polarizador

sample tube
plane-polarized
Plano
de luz
Muestra
de uan
containing
light
direction of light propagation
Polarizada
compuesto
quiral
chiral compound

the plane of polarization

viewer
planehas been
plano
de lrotated
uz analyzer
analizador
polarized

polarizada
light

from the dial and represents the difference between an optically inactive sample
the optically active sample. This is called the observed rotation (a); it is measure
degrees. The observed rotation depends on the number of optically active molec
the light encounters in the sample. This, in turn, depends on the concentration o
sample and the length of the sample tube. The observed rotation also depends on
temperature and the wavelength of the light source.
Each optically active compound has a characteristic specific rotation. The spe
rotation is the number of degrees of rotation caused by a solution of 1.0 g of the c
pound per mL of solution in a sample tube 1.0 dm long at a specified temperature
wavelength.
PlaneLuz
Polarized
Light
Can
Described
as The specific rotation can be calculated from the observed rotation u
compuesta
por
dos Be
vectores,
the following formula:
mezcla de enan-meros
Identical
Magnetic & Electric
magn-co-elctrico
Vectors; Resultant is Vertical Plane
T
[ ]

Jacobus Hendricus vant Hoff

(18521911), a Dutch chemist, was a
professor of chemistry at the University of Amsterdam and later at the
University of Berlin. He received the
first Nobel Prize in chemistry (1901)
for his work on solutions.

lc

where [a] is theCada molcula de enan-mero, rota el plano en

specific Plane
rotation;
T isLight
temperature
in C;
Polarized
Can Be Described
as l is the wavelength of th
Magnetic
& Electric
l isPor
cident light (when
sodiumIdentical
D-line
is used,
indicated
D); a issi
the las
observe
un thesen-do
(opuestos).
lo as
tanto,
Vectors; Resultant is Vertical Plane
tation; l is the length
of the sample tube
and c is the concentration
concentraciones
de in decimeters;
los enan-meros
son las o
sample in grams per milliliter of solution.
mismas,
no habr
efecto en la rotacin
el plano.
For example,
one enantiomer
of 2-methyl-1-butanol
has beendfound
to have a
+5.75.
cific rotation ofSin
Becausesi itsun
mirror
image rotates
the en
plane
of polarizatio
embargo,
ena-mero
est
exceso
si
Born in France, Jean-Baptiste Biot
amount but
in the
oppositeddirection,
Magnetic or Electric
or Electric
habr
rotacin
el plano.the specific rotation of the other e
(17741862)
was imprisoned forMagnetic
tak- same
Component Absorbed
Component
Absorbed
tiomer
must be -5.75.
ing
part in a street riot during the

Differently; Resultant Vector

Differently; Resultant Vector
French
Revolution. He became a pro-is Displaced
is Displaced

fessor of mathematics at the UniverUna

mezcla
racmica
o racemato
sity
of Beauvais
and
later a professor
Plane Polarized Light Can Be Described as
ofcorresponde
physics at the
Collge
de m
France.
a uMagnetic
na
ezcla
de
Identical
& Electric
He was awarded
theResultant
Legion of
Honor Plane
Vectors;
is Vertical
n lp.a 212.)
misma can-dad.
byenan-meros
Louis XVIII. (Also esee

PROBLEM 12

CH2OH
C
CH3

H
CH2CH3

CH2OH
H C CH3
CH2CH3

(R)-2-me3l-1-butanol
(R)-2-methyl-1-butanol

(S)-2-me3l-1-butanol
(S)-2-methyl-1-butanol

C
[ ]20
= +5.75
D

C
[ ]20
= 5.75
D

metric carbons a compound has, the more stereoisomers are possible for the com3-chloro-2-butanol
pound. If we know how many asymmetric carbons a compound has, we can calculate
the maximum number of stereoisomers for that compound: a compound can have a
H
H
H
H3C
H3C have Hany other stereocenters),
CH3
CH3
maximum of 2n stereoisomers (provided
it doesnt
Enan3meros
cOH
on the
ms
de un
centro
asimtrico
HO C C
where
number
carbons. C
For example,
HO of
C nC equals
C asymmetric
C
C OH 3-chloro-2-butanol
Cl
H
Cl
has two asymmetric carbons. Therefore,
it can have as many as four 122 = 42 H
CH3
H3C 4 Cl
H 1 CH3 The four H
Cl as
3C 2 H are shown both
3 perspective
stereoisomers.
stereoisomers
formulas
and as
n
Nmero de enan-meros 2 , donde n es el nmero de centros quirales
erythro enantiomers
threo enantiomers
Fischer projections.
perspective formulas of the stereoisomers of 3-chloro-2-butanol (staggered)
*

CH3CHCHCH3
Cl OH
3-chloro-2-butanol

Cl

H3C
C

OH

H 1 CH3

HO

CH3
C

H3C

C
2

Cl

H3C
H

H
OH

HO

Cl 3 CH3

H3C

stereoisomers of 3-chloro-2-butanol

erythro enantiomers

CH3
C
4

Cl

threo enantiomers

perspective formulas of the stereoisomers of 3-chloro-2-butanol (staggered)

CH3
OH
H
H
Cl
CH3

CH3
H
HO
Cl
H
CH3

1
2
erythro enantiomers

CH3
OH
H
Cl
H
CH3

CH3
H
HO
H
Cl
CH3

3
4
threo enantiomers

Como
representar
as proyecciones
de Fischer?
Fisher
projections
of the lstereoisomers
of 3-chloro-2-butanol
stereoisomers of 3-chloro-2-butanol

The four stereoisomers of 3-chloro-2-butanol consist of two pairs of enantiomers.

Stereoisomers 1 and 2 are nonsuperimposable mirror images. They, therefore, are

3
(
(
(
(

e C attached to O, C, H) points counterclockwise, suggesting it has the S configuraCHclockwise,

3
highest
priority
togroups
the group
with
the next
highestC-3
priority
points
suggestn. However, because
we
switched
two
before
we
drew
the
arrow,
has
the
By repeating these steps for C-3, you will find that it has the R configuration. Thus, the
ing it has
has the
the RR configuration.
because
the group
with the lowest priority is on a
posite configurationit
configuration. But
Thus,
the isomer
is named
isomer is named
(2S,3R)-3-bromo-2-butanol.
By repeating
theseC-2
steps
you will find(Section
that it has
the R con
horizontal bond, we can
conclude that
hasfor
theC-3,
S configuration
5.6).
S,3R)-3-bromo-2-butanol.
S

isomer is named
CH3 (2S,3R)-3-bromo-2-butanol.

H3C

Br

H C
HO

C H

OHS

CH3 1
Br H
OH
14

3 CH
3

Br

(2S,3R)-3-bromo-2-butanol
CH
3
CH3
(2S,3R)-3-bromo-2-butanol

CH3
H 2 OH
H

Br1

3 CH
3

The four stereoisomers of 3-bromo-2-butanol are named as shown

here. Take a few
(2S,3R)-3-bromo-2-butanol
By
repeating
steps
for C-3,
will find
it hasmanthe R configuration. Thus, the
minuteswith
to verify
theirthese
names.
Fischer projections
two asymmetric
carbons
can you
be named
in athat
similar
named (2S,3R)-3-bromo-2-butanol.
r. Just apply the stepsisomer
to eachisasymmetric
carbon thatstereoisomers
you learned forofa Fischer
pro3-bromo-2-butanol
are
named as sho
H
H
H The four
H
H3C
CH3
H3C
CH3
tion with one asymmetric carbon. For C-2,
the arrow
from
thenames.
group with the
minutes
to verify
their
CH
3
HO
C C priority
C group
C OH
C C OHsuggest-HO C C
ghest priority Br
to the
with the next highest
points
H clockwise,
Br
H
Hlowest
OH
H
H
H
H
H
C
CH
2
g it has the R configuration.
But
because
the
group
with
the
priority
is
on
a
3 H3C
CH3
Br
CH3
Br3C
H3C 3 H
H
1
4
H
Br
rizontal bond, (2S,3R)-3-bromowe can conclude that C-2
has theCS configuration
(Section
(2R,3S)-3-bromo(2S,3S)-3-bromoHO 5.6).
OH
C C Br(2R,3R)-3-bromoC
Br
H C C OH
3
2-butanol
2-butanol
2-butanol
2-butanol
CH
R
3
S 3
CH3
Br
CH
H
H3C
perspective
formulas
ofpthe
stereoisomers
of 3-bromo-2-butanol
3 de 3-bromo-2-butanol
Frmulas
erspec3va
(2S,3R)-3-bromo-2-butanol
CH eHn
31

(2R,3S)-3-bromo(2S,3S)-3-bromoCH3 are2-butanol
CH3 here.2-butanol
3
TheCH
four
stereoisomers
of 33-bromo-2-butanol
named as shown
Take a few
2
H
Br
perspective
formulas
of
the
stereoisomers
of 3-bromo-2
H
OH
HO
H
H
OH
HO
H
minutes to verify their names.
4

CH3Br

Br

H3CH
C 3

(2S,3R)-3-bromo2-butanol
CH

OH

Br

Br

CH3H

CH3 H3C CH H CH3

H
CHCH
CH3 CH3
3 3
3
repeating these steps
for C-3, you will (2R,3S)-3-bromofind that it has the R (2S,3S)-3-bromoconfiguration. Thus,(2R,3R)-3-bromothe
(2S,3R)-3-bromoOH 2-butanol HO
H2-butanol
H C OHC
HO
HO H
OH
OH
C
C
C
C
C
C
2-butanol
2-butanol
Br
H
mer is named (2S,3R)-3-bromo-2-butanol.
Br
H
H
Br
Br
H
Br
H
Fischer
projections
of
the
stereoisomers
of
3-bromo-2-butanol
de 3-bromo-2-butanol
CH
Br
CH3 Proyeccin Hd3e CFischer
H3CH
C
Br
H
CHH
CH3 3
CH3
3
3

(2S,3R)-3-bromo2-butanol H

(2R,3S)-3-bromo(2S,3S)-3-bromo(2R,3R)-3-bromo(2S,3R)-3-bromo(2R,3S)-3-bromo(2S,3S)-3-bromo2-butanol
2-butanol
2-butanol
2
2-butanol
2-butanol
2-butanol
1
4
Hperspective
Br
formulas of the stereoisomers of 3-bromo-2-butanol
Fischer projections of the stereoisomers of 3-bromo-2-

OH

2-butanol
2-butanol
3
R CH3
perspective
formulas of of
the3-bromo-2-butanol
stereoisomers of 3-b
of the stereoisomers
(2S,3R)-3-bromo-2-butanol perspective formulas
(2S,3R)-3-bromo-2-butanol

3 2-butanol

bromo-2-butanol are named

here.
Take
a few
CH
CHCH
CH3 as shown
3 CH
3 a3 few
ereoisomers of 3-bromo-2-butanol
are named
as 3shown here. Take
OH
H HOOH H
HO H H OH
verify their names. H
Enan3meros
H
Br
BrBr H
H
Br Br H H

CH3 C
H HOOH
Br HH
CH3 C

H
H
CH3
CH3
H
HCHCH
H H3CCH
H
H3C CH3 CH
CH33
3
3 3CH3
HO OH
(2S,3R)-3-bromo(2R,3S)-3-bromo(2S,3S)-3-bromo- (2S,3S)-3-bro
(2R,3R)-3
C OHC Br HO C
C C (2R,3S)-3-bromoHO
H CC BrC OH(2S,3R)-3-bromoC
C
C
C
H
H 2-butanol
2-butanol
2-butanol
2-butanol H
2-but
2-butanol
2-butano
CH
HCH
Br
H
3
3C
Br
H
HC
Br
H C BrH

Fischer projectionsFischer
of3the stereoisomers
3
3
projections3 of of
the3-bromo-2-butanol
stereoisomers of 3-b
S)-3-bromo(2S,3S)-3-bromo(2R,3R)-3-bromoomo(2R,3S)-3-bromo(2S,3S)-3-bromo(2R,3R)-3-bromobutanol
2-butanol
2-butanol
ol
2-butanol
2-butanol
2-butanol
Diasteroismeros
mulasperspective
of the stereoisomers
formulas ofof
the3-bromo-2-butanol
stereoisomers of 3-bromo-2-butanol

CH3CH3
HO OH H
Br Br H
CH3CH3

3S)-3-bromo-3-bromo2-butanol
utanol

CHCH
3 3
HO H H OH
BrBr H H
CHCH
3 3

CH3 CH3
HOOH H
H
Enan3meros
HH
Br
Br
CH3 CH3

CH3
HO
H
H
Br
CH3

(2S,3S)-3-bromo- (2S,3S)-3-bromo(2R,3R)-3-bromo- (2R,3R)-3-bromo(2R,3S)-3-bromo2-butanol

2-butanol
2-butanol
2-butanol
2-butanol

Fischer
projections ofof
the
stereoisomers of 3-bromo-2-butanol
ons of
the stereoisomers
3-bromo-2-butanol

Diasteroismeros: Son estereoismeros que no son imagen especular ni

tampoco enan-meros

is why we emphasized in Section 15.9 that the maximum 2

3
mpound with n asymmetric
carbons
can have
(provided
perspective
formulas
of the
stereoisomers of 2,3-dibromobutane (staggered
n
ocenters) is 2 , instead of stating that a compound with
The m
missing
isomer is the mirror image of 1 because 1 and its mirror ima
tereoisomers.
Compuestos
eso
Section
nd with two same
asymmetric
carbons
thatbehas
only
three
molecule.
This can
seen
more
clearly if you look either at the perspe
utane. 3:36 PM
mulas
Fischer projections.
-2003
Pagedrawn
201 in their eclisped conformations
CH3 or at the
CH3
CH3
CH3CHCHCH3
Br Br
2,3-dibromobutane
2,3-dibromobutano
H3C
H

H
C

C
Br
2

Br

CH3

H3C
H

CH3
C

Br

H
H

Br
Br
CH3
1

H3CBr
H

Br
Br
H
H CH3 H
BrH3C
CH3
CH3
2

Br

Br

CH3
C

Fischer projections of the stereoisomers of 2,3-dibromobutane

Br

Br

Br

2 identical when looking at 3the perspective

It is obvious1that 1 and its mirror image are
H
CH
3
formula in the
eclipsed
conformation.
To convinceof
yourself
that the Fischer projection
perspective
formulas
of the stereoisomers
2,3-dibromobutane
(eclipsed
of 1 and
mirror image are identical, rotate the mirror image by 180. (Remember,
C its C
H projections only by rotating them 180 inSection
Br
you can move Fischer
the plane5.10
of the M
paper.)
HC
Br
3

3
CH
CH3
CH
H3C 3
CH3
H3C 3 CH3
the stereoisomers of 2,3-dibromobutane (staggered)
H
Br
Br
H
Br C HC
H C C H
H
Br
Br
H
H H Br H
mirror image of 1 because 1 and its
the
Br mirror
Br areBr
Br image
CH3at the perspective
CH3 foren more clearlyCH
if 3you look either
superimposable
1 at the Fischer2projections. mirror
3 image
conformations or

CH3
H
Br
H
Br
CH3

CH3
Br
H
Br
H
CH3
superimposable
imagen
mirror
image

superponible
Fischer projections of the stereoisomers
2,3-dibromobutane
Stereoisomer 1 isofcalled
a meso compound. Even though a meso (mee-zo)
H3C
CH3
H
C
CH
3
3
compound has asymmetric carbons, it is an achiral molecule because it is superimposable
on C
its mirror image. Mesos is the Greek word for middle. A meso comC itsCmirror
C
that 1Hand
image
are
identical
when
looking at the perspective
Br
H
Br
pound is achiralwhen
polarized light is passed through a solution of a meso
e eclipsed
To
thatis the
Fischer
projection
compound,
the
of polarization
not rotated.
A meso
compound can be recogBr conformation.
H convince
H
Brplaneyourself

it has asymmetric carbons. A plane of symmetry cuts the molecule in half, and oneplane of
CH2CH
3
half is the mirror
image ofCH
the3 other half. Stereoisomer 1 has
a plane
of symmetry,
symmetry
H
C
CH
3
3
H notBr
H mirror
OH imageit does not
which means that it does
have a nonsuperimposable
H
H
CH2
have an enantiomer.
H C C H
H
Br
plano
planede
of
CH3
CH3 H C
symmetry
simetra
stereoisomer
1
3
H
Br

H
OH
CH2CH3
OH
CH2CH3 HO
CH3
H
OH
meso compounds
H
H
CH2
H C C H
It is easy to Hrecognize
with
two
asymmetric carbons has a
Br whenBra compound
H
OH
Br four atoms or groups bonded to one asymstereoisomer that is a meso compoundthe
OH
CH2CH3 HO
CH3
stereoisomer 1
Br

A meso

A chiral
of symm

Br

metric carbon are identical to the four atoms or groups bonded to the other asymmet- If a c
meso compounds
bons
Compuesto
meso
ric carbon. A compound with the same
four atoms
or groups bonded to two different to ea
willwhen
have three
stereoisomers:
One asymmetric
will be a meso
compound,
It asymmetric
is easy to carbons
recognize
a compound
with two
carbons
has aand of its
comp
the other that
two iswill
be enantiomers.
stereoisomer
a meso
compoundthe four atoms or groups bonded to one asymIf a com
metric carbon are identical to the four atoms or groups bonded to the
other
asymmetH
CH3
H3C
H3C
OH
H
bons ha
ric carbon. A compound
with the same four
atoms or groups bonded to two different
to each
HO
OH
C
C
C
C
C
H
C
asymmetric carbons
will have three stereoisomers:
One will be a meso compound,
and of its ste
H
H
H
compou
the other two will
CH3
H3C
CH3
OH
HObe enantiomers.
HO
a meso compound
compuesto
meso

H3C

OH
CH3
C
C
H
H
H
OH
HO H CH3OH
a meso compound
CH3

a meso compound
compuesto
meso

CH3
H
OH
H
OH

H3C
C

H
HO

enantiomers
enan3meros

CH3

CH
CH3
HO C
C H
C OH3
H
OH
HO
H
CH3 H
HO
HH3C OHOH
enantiomers
CH
CH3
3

CH3
H
OH
HO
H

enantiomers
enan3meros

CH3
HO
H
H
OH