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Alkenes

Alkenes
Alkenes are organic molecules that contain at least one carbon-carbon double bond,
which is referred to as unsaturation. Saturation is when all of the carbons have all single
bonds. If the double bonds are just next to each other, they are called cummulated dienes.
If there is only one C-C bond between two double bonds, it is called a conjugated diene.
If more than one single bond intervenes it is an isolated diene.
The double bonds in alkenes are higher in energy than single bonds and are more
reactive. Molecules will favor single bonds over double or triple ones when given a
chance.
Bond dissociation energy is the energy needed to break a bond.
Bond dissociation energy
C-C C + C 85 kcal/mole
C=C C + C 145 kcal/mole
Ethene is the smallest, simplest alkene. It is planar and the angle between its bonds is
approximately 120.
The C-H bonds are stronger in ethene than in ethane because the bond draws electron
density away from from the carbon, which draws electron density away from the
hydrogens. This makes ethene unreactive and gives the carbons sp2 character, which is
more s-like and lower in energy.

Gallery of alkenes
IUPAC
common names
CH2=CH2
ethene
ethylene
CH3CH=CH2
propene
propylene
CH2=CH2CH2CH3 1-Butene
1-Butylene
CH3CH=CHCH3 2-Butene
2-Butylene
CH2=C(CH3)2
2-Methylpropene
Isobutene
Cyclobutene
3-Methylcyclopropene

IUPAC alkene nomenclature


1. find the longest chain of carbons containing both carbons of the double bond
2. number this chain left to right and right to left and choose the method that gives
the double bond the lowest numbers

3. using the smallest of the two numbers identifying the double bond as prefix,
followed by a hyphen without spaces, name the chain as for an alkane changing
the -ane to -ene
Then follow the rest of the rules for naming halogenoalkanes

Alkenols
Alkenols are compounds containing both a double bond and an OH group.
To name, find the longest carbon chain that contains both the C=C and the OH-. The OH
group gets the higher priority (lower number). Oxygen takes precedence over carbon.

CH2=CH2CH-OH 2-Propen-1-ol or Prop-2-en-1-ol


(IUPAC name)
The "2" refers to the double bond and can go at the beginning of the name or right before
the "en".

Gallery of alkenols
IUPAC
2-Cyclohexen-1,4-diol
4-Cyclohexen-1,3-diol

Naming alkane and alkene substituents


Alkyl means a saturated substituent (all single bonds).
Alkenyl means an unsaturated substituent (en indicates a double
bond).

IUPAC name
Common name
(1-Methylcyclohexyl)ethene
1-Ethenylcyclohexanol
1-Vinylcyclohexanol
(a cyclopropane diol) 1-(1-Propenyl)-1,2-cyclopropanediol
1-(2-Propenyl)-1,2-cyclopropanediol 1-Allyl-1,2-cyclopropanediol

CH2=C=CH2
CH2=C=CH-CH3
CH2=CH-CH=CH2

Naming alkenes with multiple double bonds


Propacanadienne
Allene
1,2-Butadiene
1,3-Butadiene
1,3-Cyclopentadiene
1,3,5-Hexatriene
3-Methylene-1,4-pendadiene

Preparation of alkenes, or how to make double bonds.


R-H + X2 + (heat or light) R-X

R-X + H2O (by SN1 or SN2) R-OH

CH3CH2Br H2C=CH2 + HBr

CH3CH2-OH CH2=CH2 + H2O

CH3CH2Br CH2=CH2

H2C-CH2Br + (strong base) + CH2=CH2 (one step) ( heat)

What is ""?
is the capital Greek letter "Delta" and is used in science to
indicate a change in something. It is used as a shorthand in organic
chemistry and in this book to indicate a change in heating
conditions, that is, the addition of heat.

Rate equation
Rate = K2[CH3CH2Br][base]
1, 2, 3 all work for E2 reactions (remember that the methyl group doesnt have a second
carbon for an elimination to function).
(pictures)

E1 reactions
Elimination reactions are one way to produce alkenes.

Elimination vs Substitution ?
There are ways to predict if a reaction will follow an elimination or a substitution
mechanism or pathway.

Elimination
High temperature (the biggest
factor)
Strong base

Substitution
Low temperature
Good nucleophile (bulkiness interferes with
nucleophilicity)

Tertiary halides favor E1, SN1.

Reactions of alkenes
Bromine
Electrophilic addition reaction between Bromine and Ethene gas:

CH2=CH2 + Br2 CH2BrCH2Br

Complete Combustion
Like other hyrdrocarbons alkenes will combust in excess air or oxygen provided that
there is sufficient activation energy for the combustion reaction. The following reaction is
the complete combustion of ethene with oxygen:

CH2=CH2 + 3O2 2CO2 + 2H2O

Hydrogen Bromide
Electrophilic addition reaction between concentrated Hydrogen Bromide and Ethene gas:

CH2=CH2 + HBr CH3CH2Br


The general formula for the reaction of any alkene with HBr is:

RCH=CHR' + HBr RCH2-CHR'Br


For asymetrical alkenes such as But-1-ene the following reaction is also feasible:

RCH=CHR' + HBr RCHBr-CH2R'


Where R and R' are alkyl groups e.g. CH3 or CH3CH2

Sulphuric Acid
Electrophilic addition reaction between cold concentrated Sulphuric Acid and Ethene gas:

CH2=CH2 + H2SO4 CH3CH3SO3H


Ethyl Hydrogensulphate is hydrolysed if warmed with water:

CH3CH3SO3H + H2O CH3CH2OH + H2SO4


Overall reaction for the two steps:

CH2=CH2 + H2O CH3CH2OH