Question

Question: Draw a stepwise mechanism that shows how all three alcohols are formed from the bicyclic alkene.

Short answer

Answer

Step-by-step solution

Stability of carbocation

The formation of the major product of the alkene addition reaction depends on the stability of the carbocation. If the reaction gives secondary and tertiary carbocation intermediates, the tertiary carbocation will form the major product.

Explanation

The protonation of alkene occurs in the presence of sulfuric acid to form a secondary carbocation. The tertiary carbocation is generated by 1,2-methyl shift.

The mechanism is shown below:

Reaction mechanism