Chapter 11, Problem 23PP

Interpretation Introduction

Interpretation:

The missing reagents and intermediates A–E are to be determined.

Concept introduction:

Addition of hydrogen to alkyne in the presence of Lindlar’s catalyst is a reduction reaction and yields the corresponding alkene.

Alkenes react with peroxy acids in a syn manner and this reaction is stereospecific.

When a strong nucleophile, such as an alkoxide or a hydroxide ion, reacts with an epoxide ring, the later gets opened.

The reaction proceeds by ${\text{S}}_{\text{N}}\text{2}$ mechanism.

The attack of the alkoxide ion happens at the less hindered carbon atom.