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Chapter 10: 10-10-21 E (page 308)

Alkyl halides can be reduced to alkanes by a radical reaction with tributyltinhydride, (C4H9)3SnH in the presence of light (hv). Propose aradical chain mechanism by which the reaction might occur. The initiationstep is the light-induced homolytic cleavage of the Sn-H bondto yield a tributyltin radical.

R-X+(C4H9)3SnH鈫�hvR-H+(C4H9)3SnX

Short Answer

Expert verified

Radical chain mechanism of the reaction is:

(C4H9)3SnH鈫�hv(C4H9)3Sn路+H路(C4H9)3Sn路+RX鈫�(C4H9)3SnX+R路(C4H9)3SnH+R路鈫�(C4H9)3Sn路+RH

Step by step solution

01

Free radical reaction

Free radicals are intermediates and these are highly reactive. Free- radical mechanism takes place in the presence of free radicals and this reaction is also known as chain reaction. This reaction takes place in three different steps i.e. chain- initiation, chain鈥� propagation and chain- termination.

02

Example

This is an example halogenation reaction in which formation of carbon- carbon bond is taking place via free radical reaction mechanism.

03

Step-by-Step mechanism of above reaction

The mechanism is given below:

(C4H9)3SnH鈫�hv(C4H9)3Sn路+H路(C4H9)3Sn路+RX鈫�(C4H9)3SnX+R路(C4H9)3SnH+R路鈫�(C4H9)3Sn路+RH

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Most popular questions from this chapter

Give IUPAC names for the following alkyl halide (f):

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