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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
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.
Gallery of alkenols
IUPAC
2-Cyclohexen-1,4-diol
4-Cyclohexen-1,3-diol
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
CH3CH2Br CH2=CH2
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)
Reactions of alkenes
Bromine
Electrophilic addition reaction between Bromine and Ethene gas:
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:
Hydrogen Bromide
Electrophilic addition reaction between concentrated Hydrogen Bromide and Ethene gas:
Sulphuric Acid
Electrophilic addition reaction between cold concentrated Sulphuric Acid and Ethene gas: