597706-14-20E AID: 2419 | 23/10/2015

AID: 1112 |4/07/2017

(a)

The reaction between hexa-2, 4-diene and HCl is following:

HCl

40oC
Hexa-2,4-diene
Cl
2-Chloro-hex-3-ene

Mechanism:
The addition of HCl on hexa-2, 4 diene occurs in three steps as follows:

Step I:
In the first step addition of proton and formation of a carbocation as follows:

HCl

40oC +
CH

Hexa-2,4-diene

Step II:
In this step carbocation cation converts into more stable allylic carbocation as follows:

+ +
CH CH

Step III:
In this step allylic carbocation forms bond with chlorine ion to form product as follows:

-
Cl
+
CH

Cl
2-Chloro-hex-3-ene

(b)

The reaction between 3-methyl-penta-1,3 diene and HBr is following:

Br

HBr

40oC

3-Methyl-penta-1,3-diene 4-Bromo-3-methyl-pent-2-ene

Mechanism:
The addition of HBr on 3-methyl-penta-1, 3- diene occurs in three steps as follows:

Step I:
In the first step addition of proton and formation of a carbocation as follows:

Step II:
In this step carbocation cation converts into more stable allylic carbocation as follows:

+
+ CH
CH

Step III:
In this step allylic carbocation forms bond with bromine ion to form product as follows:

Br
-
Br
+
CH

4-Bromo-3-methyl-pent-2-ene

(c)
The reaction between 1,2dimethylene-cyclobutane and HCl is following:

HCl

40oC
Cl

1,2-Dimethylene-cyclobutane 1-Chloromethyl-2-methyl-cyclobutene

Mechanism:
The addition of HCl on 1,2dimethylene-cyclobutane occurs in three steps as follows:

Step I:
In the first step addition of proton and formation of a carbocation as follows:

Step II:
In this step carbocation cation converts into more stable allylic carbocation as follows:

+
C

+
CH2
Step III:
In this step allylic carbocation forms bond with chlorine ion to form product as follows:

-
Cl

+
CH2
Cl
1-Chloromethyl-2-methyl-cyclobutene