Which is the correct structure for E-3-bromo-2-chloro-2-pentene?

CH3 CH2CH3 CH3 Br

1. C C 2. C C
Cl Br Cl CH2CH3

CH3 CH3 Cl
CH2CH3
3. C C 4. C C
Br Br CH2CH3
Cl
 Alkenes: Stability
The stability of alkenes depends
upon number of substituents
 Stability of Disubstituted
Alkenes
H3C H H H H3C H
> >
H3C H H3C CH3 H CH3
ELECTROPHILIC ADDITION & OXIDATION

REACTION OF
ALKENES
 Reactive Sites of Alkenes &
Alkynes

CH3
H3C C CH
H3C
 Alkenes: Electrophilic
Addition
electrophil
e
R R R Z
+ Y+ + Z- R
R R
R Y R
nucleophil
e

Electrophilic addition to the double bond is a

two-step process
Alkenes: Electrophilic
Addition
Alkenes: Electrophilic
Addition
 Alkenes: AE -
Hydrogenation
CH3 CH3
Pt/C
H
+ H2
H

With the help of metal catalysts, H2 adds to

the double bond.
(Catalytic Reduction)
 Alkenes: AE -
Hydrogenation
 Alkenes: AE -
Hydrogenation
Alkenes: AE -
Halogenation
Alkenes: AE -
Halogenation
 Alkenes: AE -
Hydrohalogenation

Electrophilic reagents we can use are hydrogen halides:

HF, HCl, HBr, HI
 Alkenes: AE -
Hydrohalogenation
 Alkenes: AE - Hydration

H
CH2 CH2 HCl, trace CH2 CH2
H3C CH + H2O H3C CH
1-butene 2-butanol OH
Alkenes: AE - Hydration
 AE – Markovnikov’s Rule
HI
I+ H
H I
1-methylcycohexene 1-iodo-1-methyl- 2-iodo-1-methyl-
cyclohexane cyclohexane

Major product Minor product

We obtain both products; however, one is the

major product.

We have a regioselective reaction.

 AE – Markovnikov’s Rule
• In the addition of HX or H2O to an alkene,
H adds to the C of the double bond having
the greater number of hydrogens.
AE – Markovnikov’s Rule
AE – Markovnikov’s Rule
Carbocation Stability
Carbocation Stability
AE – Markovnikov’s Rule
AE – Markovnikov’s Rule
HBr
+
Br H
A B
H Br
1-bromo-1-methyl- 1-bromomethyl-
cyclopentane cyclopentane
AE – Markovnikov’s Rule
 Alkenes: AE – Addition of
Alcohols
Alcohols react the same way as water

+
H H3C CH3
H3C
CH3
C CH2 + CH3CH2OH
O
H3C
H2C CH3
2-methylpropene ethanol
tert-butyl-ethyl ether

Note: the reaction works only in the

presence of acid.
Alkenes: AE – Addition of
Alcohols