Exercises 6,7,8 Handout

Exercise 6
HYDROCARBONS
HYDROCARBONS
OBJECTIVES:
At the end of the exercise, the student should be able to:
develop ability to detect and record various signs of chemical

change.
describe how hydrocarbon types may be detected and

differentiated from each other by means of simple chemical
tests (test tube reactions).
compare the reactivity of alkanes, alkenes, alkynes and

aromatic hydrocarbons towards selected chemical reagents; and
carry out the laboratory preparation of acetylene.
Functional Group
is a group of atoms that has
characteristic chemical
behavior in every molecuIe
where it occurs.
(reactive sites)
The chemistry of
every organic molecule,
regardless of size and
complexity, is determined
by the functional groups
it contains.
Functional groups
Hydrocarbons
- they contain only carbon and hydrogen
Alkanes and Cycloakanes

Alkenes and Alkynes
Aromatic Hydrocarbons
Hydrocarbons
Aliphatic
Aromatic
Hydrocarbons
Aliphatic
Alkanes
Aromatic
Alkenes
Alkynes
Cyclic aliphatic
Hydrocarbons
Aliphatic
Alkanes
described as saturated hydrocarbons

have only C-C and C-H single bonds
contain the max possible # of H per C
general formula: CnH2n+2 (n is an integer)

H
Hydrocarbons
sometimes referred to as paraffins

(Latin parum affinis, meaning little affinity)
Aliphatic
Alkanes
show little chemical reactivity

do react w/ O2, halogens and few
subs under proper conditions
Hydrocarbons
sometimes called an olefin

contain a carbon-carbon double bond
general formula: CnH2n
Aliphatic
H
C
Alkenes
Hydrocarbons
contain a carbon-carbon triple bond
Aliphatic
HC
CH
Alkynes
Hydrocarbons
the carbon atoms are arranged to form

rings
Aliphatic
Cyclic aliphatic
Hydrocarbons
The most common aromatic
hydrocarbons are those that
contain a benzene ring.
H
H
Aromatic
HYDROCARBONS
Samples:
Cyclohexane
Benzene
Cyclohexene
Toluene
Acetylene
Solubility Tests
Sample
CH2Cl2
H2O
NaOH
H2SO4
cyclohexane
cyclohexene
benzene
toluene
Legend:
(+) miscible
(-) immiscible
Solubility Tests
Sample
CH2Cl2
H2O
NaOH
H2SO4
cyclohexane
cyclohexene
benzene
toluene
Legend:
(+) miscible
(-) immiscible
likes dissolves like
-HCs are soluble in CH2Cl2 but insoluble in

H2O because they are non-polar organic cpds
-CH2Cl2 is non-polar while H2O is polar
Solubility Tests
Sample
CH2Cl2
H2O
NaOH
H2SO4
cyclohexane
cyclohexene
benzene
toluene
Legend:
(+) miscible
(-) immiscible
HCs have no reaction with dilute base
Solubility Tests
Sample
CH2Cl2
H2O
NaOH
H2SO4
cyclohexane
cyclohexene
benzene
toluene
Legend:
(+) miscible
(-) immiscible
Alkenes are reactive with cold

concentrated sulfuric acid (sulfonation).
Solubility Tests
Explanation:
When alkenes are treated with cold concentrated
sulfuric acid, they dissolve because they react by
electrophilic addition to form alkyl hydrogen sulfates
(ROSO3H)
Halogenation/Bromination
Reagent: Br2/CH2Cl2
Positive Result: loss of red-orange color of Br2
(-)
(+)
Reagent: Br2/CH2Cl2
Positive Result: loss of red-orange color of Br2
Sample
Light Reaction
Dark Reaction
cyclohexane
cyclohexene
acetylene
benzene
toluene
Explanation:
CH2Cl2 serves as the solvent

- will bring Br2 in contact with the HCs
- good reaction medium since it is both non-polar and
inert towards the HCs and bromine
Bromination reaction of HCs proceed by 2 diff

mechanism:
Free Radical Substitution (FRS)

Electrophilic Substitution (EA)

requires light or heat
produce HBr as one of the products
mechanism by which alkanes and alkylbenzene
undergo bromination
Halogenation of an alkane is a FRS reaction

RH +
X2 Heat/UV
light
RX
+
HX
alkane
halogen
haloalkane
hydrogen halide

radical - highly reactive because it contains an atom
with an odd number of electrons
achieve a valence-shell octet in several ways

radical might abstract an atom and one bonding
electron from another reactant, leaving behind a
new radical
(radical substitution reaction)
Steps:
A halogen atom abstracts hydrogen from the alkane

(RH) to form an alkyl radical (R).
The radical in turn abstracts a halogen atom from a
halogen molecule to yield the alkyl halide (RX).
Which alkyl halide is obtained depends upon which
alkyl radical is formed.

Study of the halogenation of many alkanes has shown
that the rate of abstraction of H atoms is always found
to follow the sequence: 3 > 2 > 1

The relative ease with which the different classes of H
atoms are abstracted is:
Ease of abstraction of H atoms:
3 > 2 > 1 > CH4
(based on the relative stability of the free radicals)
relative stability of the free radicals:

-
the amount of E needed to form the various classes of

radicals decreases in the order:
CH 3 > 1 > 2 > 3
(abstraction of a 1 H yields a 1 radical,

abstraction of a 2 H yields a 2 radical...)

R-H
R+H
H= bond dissociation energy
if less E is needed to form one radical than another

- the one radical contains less E than the other is more
stable
Relative to the alkane from which it is formed,

Stability of free radicals:
3 > 2 > 1 > CH 3

Ease of abstraction of H atoms:
3 > 2 > 1 > CH4
Ease of formation of free radicals:

3 > 2 > 1 > CH 3
The more stable the free radical, the more easily it is
formed.
Reaction: cyclohexane
Reaction: toluene
Reaction:
toluene undergoes bromination at a faster rate despite
that it is brominated at a 1 carbon
explained by the resonance stabilization of benzyllic
free radical
Reaction:
stability of free-radical:
benzyllic > 3o > 2o > 1o > CH3
ease
of formation of free-radical:
benzyllic > 3o > 2o > 1o > CH3

simple generalization:
the reactivity of a H depends chiefly upon its class, and
not upon the alkane to which it is attached
Electrophilic Addition (EA)

can take place even in the dark
no HBr is produced
mechanism by which alkenes and alkynes are
brominated
Electrons in the bond of alkenes/alkynes react with

electrophiles
these reagents that are seeking a pair of electrons are
called electrophilic reagents (Greek: electron-loving)
Alkenes are readily converted by Br2 into saturated cpds

that contain two atoms of halogen attached to adjacent
carbons
addition proceeds rapidly at room T or below, and does

not require exposure to UV light
With alkynes the addition may occur once or twice,

depending on the number of molar equivalents of halogen
we employ:
addition proceeds rapidly at room T or below, and does

not require exposure to UV light
electrophilic addition to an alkene/alkyne involves the

intermediate formation of the more stable carbocation
Stability of carbocation:
benzyllic > 3o > 2o > 1o
Reaction: cyclohexene
Reaction: acetylene
Reaction with Baeyers Reagent

Reagent: cold, dilute, neutral KMnO4
Positive Result: disappearance of purple color of permanganate
solution and formation of brown precipitate (MnO 2)
Sample
Results
Explanation
cyclohexane
absence of unsaturation
cyclohexene
presence of unsaturation
acetylene
presence of unsaturation
benzene
presence of unsaturation but

resonance stabilized
toluene
presence of unsaturation but

resonance stabilized

Reagent: cold, dilute, neutral KMnO4
Positive Result: disappearance of purple color of permanganate
solution and formation of brown precipitate (MnO 2)
(-)
(+)

Explanation:
Alkenes: 1,2-Dihydroxylation is an important oxidative
addition reaction of alkenes. (Glycol or dihydroxy alcohols
formation)
(Heat and the addition of acid are avoided which can promote further
oxidation of the glycol, with cleavage of the carbon-carbon double
bond)

Reaction: cyclohexene
Oxidation: Alkenes can be partially oxidized by permanganate

Explanation:
Alkynes: leads to cleavage at the carboncarbon triple
bond. The products are carboxylic acids:

Reaction: acetylene
Reaction with Ammoniacal AgNO3

Reagent: Ammoniacal AgNO3 [Ag(NH3)2+]
Positive Result: formation of insoluble substance or gray ppt
Sample
cyclohexane
cyclohexene
acetylene
Results
Explanation

Reagent: Ammoniacal AgNO3 [Ag(NH3)2+]
Positive Result: formation of insoluble substance or gray ppt
Sample
Results
Explanation
cyclohexane
not a terminal alkyne
cyclohexene
not a terminal alkyne
acetylene
terminal alkyne

Reaction: acetylene
an acid-base reaction (not an oxidation)

used to detect presence of terminal alkynes
Preparation of Acetylene Gas

Reaction:
Exercise 7
ORGANIC DERIVATIVES OF WATER
OBJECTIVES:
At the end of the exercise, the student should be able to:
identify the chemical properties of organic derivatives of

water; and
observe the differences in chemical reactivity of primary,

secondary, and tertiary alcohols, phenols, and ethers
towards selected chemical reagents.
Organic Derivatives of Water
Alcohol
Phenol
Ether
Alcohol
have a hydroxyl (-OH) group bonded

to a saturated carbon atom
general formula: R-OH
classified as 1o, 2o, or 3o
Alcohol

have a hydroxyl group attached
directly to a benzene ring
Phenol
Ether
organic compounds in which two
saturated carbon atoms are bound
through a single oxygen atom
Samples:
1-Butanol
2-Butanol
tert-Butanol
Phenol
Diisopropyl ether
Solubility Tests
Sample
H2O
NaOH
H2SO4
1-butanol
2-butanol
+/-
tert-butanol
phenol
diisopropyl ether
Immiscibility can be explained by:

size of the hydrophobic parts in each molecule is
so great compared to the hydrophilic portion, thus,
rendering each molecule as water-insoluble
Solubility Tests
Sample
H2O
NaOH
H2SO4
1-butanol
2-butanol
+/-
tert-butanol
phenol
diisopropyl ether
Increasing solubility of the alcohols as

branching increase is explained in terms of the
shape of each molecule.
Solubility Tests
Sample
H2O
NaOH
H2SO4
1-butanol
2-butanol
+/-
tert-butanol
phenol
diisopropyl ether
degree of branching, molecule becomes more spherical

in shape
inc in spherical shape reduces the surface area of each
molecule, thus reducing the IMFA of the alcohol molecules
this makes it easier for water to solvate the molecules
Solubility Tests
Sample
H2O
NaOH
1-butanol
2-butanol
+/-
tert-butanol
phenol
diisopropyl ether
H2SO4
Comparative acidities of alcohols and phenols:

Both alcohols and phenols, under certain conditions,
can act as Lewis acids due to the proton (H+) present
in the molecule.
Solubility Tests
Sample
H2O
NaOH
1-butanol
2-butanol
+/-
tert-butanol
phenol
diisopropyl ether
H2SO4

However, the solubility test in NaOH clearly shows
that phenols are stronger Lewis acids than alcohols.
Solubility Tests
Explanation:
Solubility Tests
Explanation:
The differences in acidities can be explained by the
relative stabilities of the conjugate bases.
Solubility Tests
Explanation:
conjugate base of alcohol: alkoxide
e.g. butanol 1-butoxide
The negative charge on the
O atom of the butoxide is
intensified by the electron
releasing alkyl group
(CH3CH2CH2CH2-) and is
therefore destabilized.
Solubility Tests
Explanation:
conjugate base of alcohol: alkoxide
e.g. 1-butanol 1-butoxide
In fact, most alkoxides are

strong bases and will easily
attract protons to form back
the alcohols.
Solubility Tests
Explanation:
For phenol, it forms upon losing a proton the
resonance-stabilized phenoxide ion.
Solubility Tests
Explanation:
Because of the resonance forms of the phenoxide,
phenol has a greater tendency to lose a proton to form
the more stable phenoxide ion.
phenol is thus a stronger acid than butanol
Solubility Tests
Sample
H2O
NaOH
H2SO4
1-butanol
2-butanol
+/-
tert-butanol
phenol
diisopropyl ether
Solubility in H2SO4
Most organic derivatives of water are soluble in H2SO4.
This solubility test is often used to indicate the presence of
oxygen atoms in a molecule.
Solubility Tests
Explanation:
2o alcohols are oxidized to ketones
Potassium permanganate Test

Reactions: 2-butanol
Solubility Tests
Explanation:
3o alcohols dont normally react with most oxidizing
agents (no H on the C-OH to oxidize)

Reactions: tert-butanol
Solubility Tests
Explanation:
reaction of a phenol with strong oxidizing agents
yields a quinone

Reaction: phenol
Lucas Test
Reagent: HCl-ZnCl2
Positive Result: appearance of cloudiness due to (alkyl chloride
formed)
Sample
1-butanol
2-butanol
tert-butanol
Result
Lucas Test
Reagent: HCl-ZnCl2
Positive Result: appearance of cloudiness due to (alkyl chloride
formed)
Sample
Result
1-butanol
2-butanol
tert-butanol
Lucas Test
Left to right: 1, 2 & 3 alcohol
immediately after addition of Lucas reagent
Lucas Test
2 minutes after addition of Lucas reagent
Lucas Test
Lucas Test
Note:
1 alcohols do not turn cloudy
2 alcohols turn cloudy after
2-5 minutes
3 alcohols turn cloudy
instantly with addition of Lucas
reagent
Lucas Test
The time required for

cloudiness to appear is a
measure of the reactivity of
the alcohol.
3 alcohols reacts
immediately with the Lucas
reagent
2 alcohols reacts within
five minutes
1 alcohols does not react
appreciably
Lucas Test
Reactions:
KMnO4 and Lucas Test

The KMnO4 and Lucas test may be used in combination
to classify alcohols as primary, secondary and tertiary.
Alcohol
KMnO4
Lucas
1 ROH
2 ROH
3 ROH
Ferric Chloride Test

Reagent: FeCl3
Positive Result: formation of a colored (usually purple or red) complex
Sample
Result
1-butanol
phenol

Left to Right: Hydrocarbon and Phenol reacted with 1% FeCl 3
(-)
(+)
Note:
formation of red color indicates
positive results and therefore the
presence of an aromatic
compound

Reactions:
A (+) reaction with the test is indicated by a distinct color

change.
Phenols are usually confirmed using this test.
form colored complexes, ranging from green through blue
and violet to red, with ferric chloride
Tollens Test
Reagent: Ag(NH3)2+
Positive Result: formation of silver mirror
Sample
Result
1-butanol
2-butanol
phenol
Tollens Test
Reagent: Ag(NH3)2+
(+)
(-)
Tollens Test
Reactions:
A (+) Tollens' test is given by easily oxidized compounds.
Iodoform Test
Reagent: I2/KI
Positive Result: formation of yellow precipitate
Sample
Result
1-butanol
2-butanol
Iodoform Test
Left to right: methyl ketone, 2-butanol and alkane
an alcohol of the structure
yields a yellow precipitate of

iodoform (CHI3)
Iodoform Test
Iodoform Test
Note:
Formation of pale yellow precipitate
indicates positive test for the
presence of methyl ketones.
2-Butanol is oxidized to 2butanone which is a methyl ketone.
it will also produce a pale yellow
precipitate
Iodoform Test
The reaction involves oxidation, halogenation, and cleavage.
Iodoform Test
Generalization:
Sample
Hot Acidic
KMnO4
Lucas Test
FeCl3
Tollens Test
1 ROH
2 ROH
3 ROH
Ar-OH
NA
R-O-R
NA
Exercise 8
CARBONYL COMPOUNDS AND

CARBOHYDRATES
CARBONYL COMPOUNDS AND CARBOHYDRATES
OBJECTIVES:
At the end of this laboratory exercise, the student should
be able to:
identify the chemical properties of carbonyl compounds
and carbohydrates
to recognize the similarities and differences in the
chemical reactivity of aldehydes and ketones; and
to apply chemical tests that distinguish among the
different types of carbohydrates.
CARBONYL COMPOUNDS
Solubility Test (in H2O)

Sample
Result
benzaldehyde
acetone
glucose
starch
solubility of carbonyl compounds

(presence of polar groups)
Solubility Test (in H2O)

Samples:
Benzaldehyde
Glucose
Acetone
Starch
Reaction with 2,4-DNP

Reagent: 2,4-dinitrophenylhydrazine
Positive Result: yellow to orange precipitate
Sample
Result
acetaldehyde
acetone

Left to right: aldehyde, ketone and amine
Note:
precipitate indicates (+)
test for aldehydes and
ketones
while yellow solution

indicates (-) test

Explanation:
Aldehydes and ketones can be differentiated from
non-carbonyl cpds through their reactions with
derivatives of ammonia

Explanation:

Explanation:
reactions with other derivatives of ammonia

Explanation:
2,4-DNP used a general test for carbonyl cpds
form C = N derivatives of aldehydes and ketones

Reaction: acetone
Tollens Test
Reagent: Ag(NH3)2+
Sample
Result
acetaldehyde
acetone
Tollens Test
Explanation:
Tollens test is used to differentiate aldehydes from ketones
based on their ability to be oxidized
aldehydes - easily oxidized to carboxylic acids
oxidation of the aldehyde is accompanied by reduction of silver

ion to free silver (metallic silver) silver mirror test
ketones - inert to most oxidizing agents
oxidation takes place only under vigorous conditions
Iodoform Test
Reagent: I2/KI
Positive Result: formation of yellow precipitate
Sample
Result
cyclohexanone
acetone
Iodoform Test
a haloform reaction that

converts methyl ketones to
carboxylic acids
when iodine is the halogen
component, the bright yellow
solid iodoform (CHI3) results.
Iodoform Test
Iodoform test is used to

detect methyl ketones and
methyl 2 alcohols
Iodoform Test
Reaction:
CARBOHYDRATES
often have the formula C x(H2O)y - hydrates of carbon
simple carbohydrates are also known as sugars or
saccharides (Latin saccharum, Greek sakcharon, sugar) and the
ending of the names of most sugars is ose
usually defined as polyhydroxy aldehydes and ketones
substances that hydrolyze to yield polyhydroxy
aldehydes and ketones
they exist primarily in their hemiacetal or acetal forms
CARBOHYDRATES
Classification based on whether the carbohydrate can be
broken down into smaller units:
monosaccharides - simplest CHO, those that cannot be
hydrolyzed into simpler carbohydrates
disaccharides - CHO that undergo hydrolysis to produce
only 2 molecules of monosaccharide
oligosaccharides CHO that hydrolyze to yield 210
molecules of monosaccharide
polysaccharides - CHO that yield a large number of
molecules of monosaccharides (>10)
CARBOHYDRATES
Monosaccharides
further classified as either aldoses or ketoses
ose suffix designates a carbohydrate

aldo- and keto- prefixes identify whether aldehyde or ketone
CARBOHYDRATES
Monosaccharides
further classified as either aldoses or ketoses
ose suffix designates a carbohydrate

aldo- and keto- prefixes identify whether aldehyde or ketone
CARBOHYDRATES
Monosaccharides
D (dextrorotatory) and L (levorotatory) designations of
D sugars have the -OH on their penultimate carbon on the

right
CARBOHYDRATES
Monosaccharides
Addition of an alcohol to an aldehyde:
The product is called a hemiacetal (-OH and OR attached to

the same carbon).
CARBOHYDRATES
Monosaccharides
Ketones undergo analogous addition reactions with alcohols.
The initial product is a reactive hemiketal (two R groups, one

OH, and one OR).
CARBOHYDRATES
Monosaccharides
undergo cyclization
to form hemiacetals
and hemiketals
nucleophilic
addition of the OH
group on C-5
CARBOHYDRATES
Monosaccharides
undergo cyclization
to form hemiacetals
and hemiketals
CARBOHYDRATES
Monosaccharide addition reactions
alcohol
aldehyde
-glucose
CARBOHYDRATES
Hemiacetal:
one H
one OH
one OR
one -R
CARBOHYDRATES
Monosaccharides
2 possible
configurations on the
hemiacetal and hemiketal:
a). -anomer - -OH
group on anomeric C is
oriented downward
b). -anomer - -OH
group is oriented upward
CARBOHYDRATES
Disaccharides
two monosaccharides joined by glycosidic bond
example:
Lactose composed of D-galactose and D-glucose
Only the anomeric carbon of D-galactose is involved in the formation
of glucosidic bond between D-galactose and D-glucose. That of Dglucose if left free.
CARBOHYDRATES
Disaccharides
two monosaccharides joined by glycosidic bond
example:
Sucrose composed of D-glucose and D-fructose
Both the anomeric carbon of D-glucose and D-fructose are used in the
formation of glycosodic bond.
CARBOHYDRATES
Polysaccharides
composed of several monosaccharide units
examples:
Starch composed of D-glucose units; orientation of

anomeric carbon is
CARBOHYDRATES
Polysaccharides
composed of several monosaccharide units
examples:
Cellulose made up of D-glucose units, but glycosidic bonds
formed are - at the anomeric carbon
Hydrolysis of Di- and Polysaccharides

Explanation:
Sample
Hydrolysis
Reaction
sucrose
sucrose:
D-glucose + D-fructose
starch
cellulose
Sucrose is hydrolyzed easily since only

one glycosidic linkage per molecule has
to be broken.

Explanation:
Sample
Hydrolysis
Reaction
sucrose
sucrose:
starch
sucrose:
cellulose
Starch is hydrolyzed because the glycosidic bond is hydrolysable (less
stable than the -glycosidic bond).

Explanation:
Sample
Hydrolysis
Reaction
sucrose
sucrose:
starch
sucrose:
cellulose
Cellulose is not hydrolyzed due to orientation is glycosidic bond which is

stable.
Molisch Test
Reagent: 10% naphthol in ethanol
Positive Result: purple color at the interface
(-)
(+)
Molisch Test
Reagent: 10% naphthol in ethanol
Positive Result: purple color at the interface
Sample
Result
cyclohexanone
glucose
sucrose
starch
Molisch test is a general test for the presence of

carbohydrates
monosaccharides give a rapid (+) test
disaccharides and polysaccharides react slower
Molisch Test
Explanation:
reaction involves hydrolysis of
glycosidic bond followed by
formation of furfural and
hydroxymethyl furfural
furfurals further react with

naphthol present in the reagent
to produce a purple product
Benedicts Test
Reagent: Cu2+ in Na citrate solution
Positive Result: formation of brick red precipitate
(+)
(+)
(-)
Benedicts Test
Explanation:
Benedicts test is used to differentiate between reducing and
non-reducing sugars
sugars that give (+) tests with Benedicts solutions (known as

reducing sugars) contain a hemiacetal group
CHOs that contain only acetal groups do not give (+) tests
with Benedicts solutions, and they are called non-reducing
sugars
CARBOHYDRATES
Hemiacetal:
one H
one OH
one OR
one -R
CARBOHYDRATES
CARBOHYDRATES
Benedicts Test
Explanation:
noncyclic aldehydes or -hydroxy ketones - undergo the oxidation

in order for oxidation to occur, the cyclic form must first ringopen to give the reactive aldehyde or -hydroxy ketones
Benedicts Test
Explanation:
reducing sugars reduce the Cu2+ to Cu+ which forms as a red

precipitate (copper(I) oxide)
Benedicts Test
Explanation:
Sample
Result
glucose
fructose
sucrose
lactose
sucrose hydrolysate
starch hydrolysate
cellulose hydrolysate
All monosaccharides give

(+) results due to availability
of the anomeric carbon.
all monosaccharides are
reducing sugars
Benedicts Test
Explanation:
Sample
Result
glucose
fructose
sucrose
lactose
sucrose hydrolysate
starch hydrolysate
In sucrose, both potential

carbonyl groups of fructose
and glucose are used in
glycosidic bond, hence nonreducing.
Benedicts Test
Explanation:
Sample
Result
glucose
fructose
sucrose
lactose
sucrose hydrolysate
starch hydrolysate
In lactose, the potential

carbnyl group of the glucose
unit is not used in the
glycosidic bond; hence it is
free (reducing sugar)
Benedicts Test
Explanation:
Sample
Result
glucose
fructose
sucrose
lactose
sucrose hydrolysate
starch hydrolysate
Hydrolysis of sucrose yields

the monosaccharides
glucose and fructose which
are reducing sugars.
Benedicts Test
Explanation:
Sample
Result
glucose
fructose
sucrose
lactose
sucrose hydrolysate
starch hydrolysate
In starch, hydrolysis yields

glucose (reducing sugar).
Benedicts Test
Explanation:
Sample
Result
glucose
fructose
sucrose
lactose
sucrose hydrolysate
starch hydrolysate
In cellulose, no hydrolysis
takes place.
Osazone Test
Reagent: phenyl hydrazine HCl
Positive Result: formation of yellow orange precipitate/crystals
Sample
Reaction time*
fructose
2 min
glucose
5 min
sucrose
30 min
lactose
Crystals formed are soluble in hot

H2O and crystallizes upon cooling
* the time required in forming crystals is used to

identify the carbohydrate
Osazone Test
Reagent: phenyl hydrazine HCl
Positive Result: formation of yellow orange precipitate/crystals
Osazone Test
Explanation:
Phenylhydrazine reacts with carbonyl compounds to
produce phenyhydrazones (osazones)
Osazone Test
Explanation:
with enough phenylhydrazine, 3 molar equivalents of

phenylhydrazine are consumed and a second
phenylhydrazone group is introduced at C2
Osazone Test
Explanation:
with enough phenylhydrazine, 3 molar equivalents of

phenylhydrazine are consumed and a second
phenylhydrazone group is introduced at C2
The real value of infinity

is known when we open the
first page of our notebook on the
night before exam and see the number of
pages to be read.. ! :D

Exercises 6,7,8 Handout

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Exercise 6

develop ability to detect and record various signs of chemical

describe how hydrocarbon types may be detected and

compare the reactivity of alkanes, alkenes, alkynes and

carry out the laboratory preparation of acetylene.

Alkanes and Cycloakanes

described as saturated hydrocarbons

general formula: CnH2n+2 (n is an integer)

sometimes referred to as paraffins

show little chemical reactivity

sometimes called an olefin

contain a carbon-carbon triple bond

the carbon atoms are arranged to form

likes dissolves like

-HCs are soluble in CH2Cl2 but insoluble in

HCs have no reaction with dilute base

Alkenes are reactive with cold

CH2Cl2 serves as the solvent

Bromination reaction of HCs proceed by 2 diff

Free Radical Substitution (FRS)

Free Radical Substitution (FRS)

Halogenation of an alkane is a FRS reaction

Free Radical Substitution (FRS)

achieve a valence-shell octet in several ways

Free Radical Substitution (FRS)

Free Radical Substitution (FRS)

A halogen atom abstracts hydrogen from the alkane

Free Radical Substitution (FRS)

Free Radical Substitution (FRS)

Free Radical Substitution (FRS)

relative stability of the free radicals:

the amount of E needed to form the various classes of

(abstraction of a 1 H yields a 1 radical,

Free Radical Substitution (FRS)

H= bond dissociation energy

if less E is needed to form one radical than another

Free Radical Substitution (FRS)

Relative to the alkane from which it is formed,

3 > 2 > 1 > CH 3

Free Radical Substitution (FRS)

Ease of formation of free radicals:

Free Radical Substitution (FRS)

Free Radical Substitution (FRS)

Free Radical Substitution (FRS)

Free Radical Substitution (FRS)

benzyllic > 3o > 2o > 1o > CH3

Electrophilic Addition (EA)

Electrophilic Addition (EA)

Electrons in the bond of alkenes/alkynes react with

Electrophilic Addition (EA)

Alkenes are readily converted by Br2 into saturated cpds

addition proceeds rapidly at room T or below, and does

Electrophilic Addition (EA)

Electrophilic Addition (EA)

With alkynes the addition may occur once or twice,

addition proceeds rapidly at room T or below, and does

Electrophilic Addition (EA)

electrophilic addition to an alkene/alkyne involves the

Electrophilic Addition (EA)

Electrophilic Addition (EA)

Reaction with Baeyers Reagent

presence of unsaturation but

presence of unsaturation but

Reaction with Baeyers Reagent