Question

Acid-catalyzed hydrolysis of a 1,2-epoxycyclohexane produces a transdiaxial 1,2-diol. What product would you expect to obtain from acidic hydrolysis of cis-3-tert-butyl-1,2-epoxycyclohexane? (Recall that the bulky tert-butyl group locks the cyclohexane ring into a specific conformation.)

Short answer

The expected product of acidic hydrolysis of cis-3-tert-butyl-1,2-epoxy cyclohexane is shown below:

Step-by-step solution

Acid Catalysis

The reaction that carried out in the presence of acid is an acid catalyzed reaction. The acid catalysed reaction of epoxide can take place by both mechanism ${\mathbf{SN}}^1$and${\mathbf{SN}}^2$ mechanism.A mixture of products is formed that are major and minor.

Result

When cis-3-tert-butyl-1,2-epoxy cyclohexane is acid catalyzed the final product is trans diaxial-1,2-diol.

The expected product of acidic hydrolysis of cis-3-tert-butyl-1,2-epoxy cyclohexane is shown below:

Expected product of acidic hydrolysis