Question

Predict the oxidation product of treating dihydro naphthalene with the reagents shown below. Only draw one enantiomer if more than one is possible. Include H's on chirality centers. (mCPBA = meta-chloroperoxybenzoic acid)



(1) mCPBA, CH2CL2
----------------------->
dihydro naphthalene (2) H+, H2O

Answer 1

Concepts and reason

The concept used to solve this problem is epoxidation of the double bond using meta chloro perbenzoic acid followed by the reaction with acid.

Fundamentals

Epoxidation is the addition of single oxygen atom the double bond.

Under acidic conditions, the nucleophile preferentially attacks the more substituted ring carbon.

Under basic or neutral conditions, the nucleophile preferentially attacks at the less substituted (or less sterically hindered ring carbon).

The reaction is as follows:

The reaction is as follows:

Ans:

The oxidation product is as follows: