3.

Electrophilic Addition on
Alkynes & Alkadienes
Reaction Mechanisms 13

Anupam Gupta
Anupam Gupta
B.Tech & M.Tech - IIT Delhi

10+ Years Total Experience

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Electrophilic Addition on
Alkynes & Alkadienes
Reaction Mechanisms 13

Anupam Gupta
 Reaction Mechanism

Nucleophilic substitution reaction:

Elimination reactions: Addition reactions:

● SN2 ● E1 ● Nucleophilic Addition to

● SN1 ● E2 carbonyls

● SNi ● E1cB ● Electrophilic Addition to

● SN2Ar ● Ei pi-bonds

● SN2Th
● Benzyne Mechanism

Electrophilic Substitution reactions

● EAS
 Electrophilic Addition to Alkynes
General Reaction
Addition of Halogen (Halogenation)
Addition of Halogen (Halogenation)
Addition of HOX
 Addition of HOX

1. Two molecules of HOX can be added. the end product is α, α-Dihaloketone.

2. The intermediate product is an enol which gives a minor product α-haloketone.
Addition of Hydrogen Halides (+HX)
 Addition of Hydrogen Halides (+HX)

Mechanism
 Addition of Hydrogen Halides (+HX)

1. Markovnikov's Addition in both steps.

2. If two moles of HX are added the final product is Gem dihalide.
3. Electrophilic addition to terminal alkyne is regioselective.
Which will form 2, 2 - Dibromopropane with HBr ?

A. CH2 = CH - CH3 B. CH3 - C ≡ CH3

C. D. Both B & C
What is the product when one mole of Pent-1-yne treated with two
moles of HCl?
A. 1, 2-Dichloropentane
B. 2, 3-Dichloropentane
C. 1, 1-Dichloropentane
D. 2, 2-Dichloropentane
The reaction of one equivalent of HBr with CH2 = CH - CH2- C ☰ CH gives

A. CH2 = CH - CH2 - C ☰ CBr

B. CH2 = CH - CH2 - C = CH2

l
Br

C. CH3 - CH - CH2 - C ☰ CH
l
Br

D. CH2 = CH - CH2 - CH = CHBr

The reaction of one equivalent of HBr with CH2 = CH - C ☰ CH gives

A. CH2 = CH - C ☰ CBr

B. CH2 = CH - C = CH2
l
Br

C. CH3 - CH - C ☰ CH
l
Br

D. CH2 = CH - CH = CHBr
Addition of H2O (Hydration Reaction)
Addition of H2O (Hydration Reaction)
 Hg2+/H+
Ph - C ☰ C - CH3 A, A is:

[JEE 2003]

A. B.

C. D.
Alkadienes
In the following reaction, the major product is

[IIT 2015; Main 2021]

A. B.

C. D.
The product(s) via-oxymercuration (HgSO4 + H2SO4) of 1-Butyne would be :
O
II
A. CH3 - CH2 - C - CH3

B. CH3 - CH2 - CH2 - CHO

C. CH3 - CH2 - CHO + HCHO

D. CH3 - CH2 - COOH + HCOOH

A. B.

C. D.
At given temperature, these reaction tell about control of reaction which is :

(1) (2)
A. Kinetic Thermodynamic
B. Thermodynamic Kinetic
C. Kinetic Kinetic
D. Thermodynamic Thermodynamic
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