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Chapter 20: Q-6-8P (page 1038)

(a) Propose a mechanism for the following reaction:

(b) Use the bond-dissociation enthalpies given in Table 4-2 (page 203) to calculate the value of 鈭咹掳 for each step shown in your mechanism. (The BDE for is about 280 kJ/mol, or 67 kcal/mol.) Calculate the overall value of 鈭咹掳 for the reaction. Are these values consistent with a rapid free-radical chain reaction?

Short Answer

Expert verified

1) Chain initiation

In this step bromine free radical is formed.

2) The second step is the chain propagation step. Thebrmonie free radical reacts with the hydrogen atom of an allylic carbon atom.

3) Chain termination reaction

The required product, the alkyl halide, will be formed in this.

Step by step solution

01

Homolytic fission

When a halogen molecule undergoes homolytic fission, it forms free radicals. These free radical intermediates are highly reactive and react with alkanes and form the respective alkyl halides.

02

 Mechanism

The mechanism of the reaction involves the following steps:

4) Chain initiation

In this step bromine free radical is formed.

5) The second step is the chain propagation step. The bromine free radical reacts with the hydrogen atom of an allylic carbon atom.

6) Chain termination reaction

The required product, the alkyl halide, will be formed in this.

03

Step 3:Explanation

Thus, alkyl halides can be synthesized from the saturated hydrocarbons on reactin with halogens in the presence of light.

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