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Alkenes

Alkenes are unsaturated hydrocarbons characterized by a carbon-carbon double bond, with the general formula CnH2n. They can exhibit geometric isomerism, classified as cis/trans or E/Z, and are named by modifying the alkane nomenclature to include the double bond location. Alkenes are significant in biological molecules and can be prepared through various methods, including dehydrohalogenation and dehydration, and they participate in numerous chemical reactions such as hydrogenation and halogenation.

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11 views30 pages

Alkenes

Alkenes are unsaturated hydrocarbons characterized by a carbon-carbon double bond, with the general formula CnH2n. They can exhibit geometric isomerism, classified as cis/trans or E/Z, and are named by modifying the alkane nomenclature to include the double bond location. Alkenes are significant in biological molecules and can be prepared through various methods, including dehydrohalogenation and dehydration, and they participate in numerous chemical reactions such as hydrogenation and halogenation.

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ALKENES

Alkenes CnH2n “unsaturated” hydrocarbons

H H
C2H4 ethylene C C
H H
Functional group = carbon-carbon double bond
C3H6 propylene

C4H8 butylene

CH3CH=CHCH3
β-butylene
isobutylene
2-butene 2-methylpropene
there are two 2-butenes:

H H H CH3
C C C C
H3C CH3 H3C H

cis-2-butene trans-2-butene

Diastereomers
C=C are called “vinyl” carbons

If either vinyl carbon is bonded to two equivalent groups,


then no geometric isomerism exists.

CH3CH=CHCH3 CH3CH2CH=CH2
yes no

CH3
(CH3)2C=CHCH3 CH3CH=CCH2CH3
no yes
E/Z system is recommended by IUPAC for the designation
of geometric isomerism.
1. Use the sequence rules to assign the higher priority * to
the two groups attached to each vinyl carbon.
2. * * *

*
(Z)- “zusammen” (E)- “entgegen”
together opposite
* *
H3C CH2CH3
C C (Z)-
H CH3

*
H3C Cl
C C (E)-
H Br
*
Nomenclature, alkenes:
1. Parent chain = longest continuous carbon chain that
contains the C=C.
alkane => change –ane to –ene
prefix a locant for the carbon-carbon double bond using
the principle of lower number.
2. Similar to alkanes
3. If a geometric isomer, use E/Z (or cis/trans) to indicate
which isomer it is.
* *
H3C CH2CH3
C C
(Z)-3-methyl-2-pentene
H CH3
(3-methyl-cis-2-pentene)

*
H3C Cl
C C (E)-1-bromo-1-chloropropene
H Br
*
CH3
CH3CH2 CHCH2CH3
\ /
C=C 3-ethyl-5-methyl-3-heptene
/ \
CH3CH2 H (not a geometric isomer)
-ol has the priority when naming

CH2=CHCH2-OH 2-propen-1-ol

CH3CHCH=CH2 3-buten-2-ol
OH
Physical properties:
non-polar or weakly polar
no hydrogen bonding
low mp/bp similar to alkanes
Insoluble in water

Importance:
common group in biological molecules
Preparation of alkenes:

1. dehydrohalogenation of alkyl halides

2. dehydration of alcohols

3. dehalogenation of vicinal dihalide


2. dehydration of alcohols
1. dehydrohalogenation of alkyl halides

| | | |
—C—C— + KOH(alc.)  —C=C— + KX + H 2O
| |
H X
3. dehalogenation of vicinal dihalides

| | | |
—C—C— + Zn  —C=C— + ZnX2
| |
X X

eg.
CH3CH2CHCH2 + Zn  CH3CH2CH=CH2 + ZnBr2
Br Br
H+
R-OH

KOH
R-X Alkene
(alc.)

Zn

vicinal
dihalide
3. Reduction of alkynes
Reactions of Alkenes

Addition of hydrogen
Addition of halogens
Addition of hydrogen halides
Addition of hydrogen halides
Additon of water
Halohydrin formation
Dimerization
Alklyation
Oxymercuration-Demercuration
Hydroboration-Oxidation
Polymerization
Hydroxylation

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