Question

In: Chemistry

Draw the major monobromination product when the following Allan's is subjected to radical bromination at 25 ℃

Draw the major monobromination product when the following Allan's is subjected to radical bromination at  25 ℃. If there is more than one product,both may be drawn in the same box.

Solutions

Expert Solution

This would undergo what is called radical halogenation. The product would be 2-bromo-2,4-dimethylpentane. The heat causes the sigma bond in the bromine molecule to split and form two bromine radicals. One of these bromine radical will perform a radical hydrogen abstraction of the hydrogen atom at the 2-position of 2,4-dimethylpentane and form a tertiary radical. This alkyl radical will then either react with the other bromine radical or another bromine molecule to form the product. I hope this helps!

Photoinduced bromination of 2,4-dimethylpentane can give three different products having a single bromo substituent. The relative amounts of each is according to the relative reactivity of 3° > 2° > 1° hydrogens and the product formed is in the ratio of 1:82:1640.


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