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CHAPTER 12
HYDROCARBONS

12.2 Alkenes

Learning Outcomes
At the end of this topic, students should be able to:
a)

Describe alkenes as unsaturated hydrocarbon with the general formula
CnH2n, n≥2.

(b)

Draw the structures and name the compunds according to the IUPAC nomenclature for:
i)

straight chain and branched alkenes

(parent chain ≤ C10) ii) cyclic alkenes (C3-C6)

iii)

simple dienes (C4-C6)
2

Learning Outcomes
At the end of this topic, students should be able to:
c) Show the preparation of alkenes through:

i) dehydration of alcohols ii) dehydrohalogenation of haloalkanes
d) Write the mechanism for c(i)
e) State Saytzeff’s Rule.
f)

Deduce the major product of elimination reaction. 3

Alkenes
- General formula CnH2n , n  2.
- Functional group  C=C double bond

- Unsaturated hydrocarbon
- C═C  1 σ bond and 1 π bond

A
B

C=C

A
B

Restricted rotation of carbon-carbon double bond causes cis-trans isomerism

4

Alkenes
Cycloalkenes
- General formula CnH2n-2
- Isomeric to alkynes CnH2n-2
Example : C4H6

CH2

CH

CH2

Functional group isomerism CH

CH3C – CCH3

5

Alkenes
Common Names Of Alkenes
Many older names for alkenes are still in use … example: CH2

CH3

CH2

ethene
 ethylene
CH2

CH

CH3

CH2

2–methylpropene
 isobutylene

CH3

CH3

propene
 propylene

C

CH3

C

CH

CH2

2–methylbut-1,3-diene
6
 isoprene

Alkenes
IUPAC Nomenclature
1. Determine the parent name by selecting the longest chain that contains the double bond

and change the ending ‘-ane’ in alkane to
‘-ene’.
2. When the chain contains more than three carbon atoms, numbering is needed to indicate the location of the double bond.
3. The chain is numbered starting from the end closest to the double bond.
4. Indicate the position of the substituent by the number of the carbon atoms to which they
7
are attached to.

Alkenes
IUPAC Nomenclature
Try this … 1

CH3

CH

CH

H3 C

Cl

CH

CH

CH3

CH3
H3C

CH

CH

CH
CH2

CH2

Br
8

Alkenes
IUPAC Nomenclature
Try this … 2
CH3
HC

Br
C
H3C

CH3

C
Br

9

Alkenes
IUPAC Nomenclature
Try this … 3
CH3

H3C
C
Br

Br

CH3
C

C
Br

H3C

C
Br

Cis isomers have higher boiling points.
Reason :
Cis is a polar molecular and trans is a non-polar!
Cis – isomers have stronger Van der Waals forces, higher boiling point.
10

Alkenes
IUPAC Nomenclature
Try this … 4
H

CH3
C

H3C

CH3

H3C
C

C
H

H

C
H

Cis isomers have higher boiling points.
Reason :
Alkyl group is electron donating group, so… cis is a polar molecular and trans is a non-polar!
Cis – isomers have stronger Van der Waals forces, higher boiling point. 11

Alkenes
IUPAC Nomenclature
5. If more than one double bond present, change from - ene to : diene – 2 double bonds triene – 3 double bonds
CH3
CH
H3C

C
C

CH3
CH

Cl
12

Alkenes
IUPAC Nomenclature
6. In Cycloalkenes :
Number the carbon atoms with a double bond as 1 and 2, in the direction that gives the substituent encountered first with a small number.

CH3
Br C

CH

H2C

CH
CH
CH3

3-bromo-3,5-dimethylcyclopentene

Alkenes
IUPAC Nomenclature
Try this …
1

H3 C isopropyl HC

ene

2

Br

bromo

3

6

CH3

H3 C
5

ene

methyl

4

3-bromo -6-isopropyl -3-methyl cyclohexa-1,4-diene

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