Q49E - Organic Chemistry (Mcmurry)

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.)

Step-by-Step Solution

Answer

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

Step 1: 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.

Step 2: 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