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Chapter 14: 27Ea (page 447)

What product (s) would you expect to obtain from reaction of 1,3-cyclohexadiene with each of the following?

(a) 1 mol Br2inCH2Cl2

Short Answer

Expert verified

1,3 cyclohexadiene is a an unsaturated six member ring where two conjugated double bonds are present. When conventional alkenes undergo halogenation (chlorination and bromination), vicinal di halides (halogen atoms on adjacent carbon atoms) are obtained. But dienes react differently with halogens (Br2).Reaction of 1,3-cyclohexadiene with 1 mol of Br2inCH2Cl2gives to isomeric products (dibromo derivatives).

Reaction

Step by step solution

01

Reaction of 1,3-cyclohexadiene with 1 mol of Br2in CH2Cl2

1,3 cyclohexadiene is a an unsaturated six member ring where two conjugated double bonds are present. When conventional alkenes undergo halogenation (chlorination and bromination), vicinal di halides (halogen atoms on adjacent carbon atoms) are obtained. But dienes react differently with halogens (Br2).Reaction of 1,3-cyclohexadiene with 1 mol of Br2inCH2Cl2gives to isomeric products (dibromo derivatives).

Reaction

02

Explanation

The reason for the formation of two isomeric products is that, the carbocation formed during the reaction is resonance stablised, leading to the formtation of two products.

Reaction

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Adiponitrile, a starting material used in the manufacture of nylon, can be prepared in three steps from 1,3-butadiene. How would you carry out this synthesis?

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