Answer to Question #255723 in Organic Chemistry for moore

Question

In the following reaction, the expected product 3-Chloro-2,2-dimethyl-butane, is only produced in small amounts whilst the seemingly unusual product, 2-Chloro-2,3-dimethyl-butane is produced in large quantities.

 

The reason for this is:

A.

The major product is obtained first, in line with Markovnikov’s rule then undergoes elimination and addition once again to give the observed major product.

B.

The reaction is one of those rare instances in which Markovnikov’s rule does not apply.

C.

The initially formed secondary carbocation rearranges by a shift of a methyl group to generate a more stable tertiary carbocation which is then attacked by Cl- to give the observed major product.

D.

The initially formed secondary carbocation rearranges by a shift of a hydrogen to generate a more stable tertiary carbocation which is then attacked by Cl- to give the observed major product.

Answer 1

C.

The initially formed secondary carbocation rearranges by a shift of a methyl group to generate a more stable tertiary carbocation which is then attacked by Cl- to give the observed major product.