Chapter 9.9, Problem 32ATS

(a)

Interpretation Introduction

Interpretation:

Product should be found for the given alkenes while treating with ozone followed by DMS.

Concept introduction:

• Anti-dihydroxylation: two hydroxyl groups adding across the double bond from both the planes is known as anti-dihydroxylation.
• This anti-hydroxylation happens when alkene is treated with peroxy acids followed by aqueous acid.
• In this reaction, intermediate is three membered cyclic oxonium ion (epoxide formation), this cyclic strain will be revealed by the attack of nucleophile (water) molecule.

To find: the structure of ${\text{C}}_{\text{6}}{\text{H}}_{\text{12}}$, which gives non-chiral product during anti-hydroxylation reaction.

 (b)

Interpretation Introduction

Interpretation:

Product should be found for the given alkenes while treating with ozone followed by DMS.

Concept introduction:

• Anti-dihydroxylation: two hydroxyl groups adding across the double bond from both the planes is known as anti-dihydroxylation.
• This anti-hydroxylation happens when alkene is treated with peroxy acids followed by aqueous acid.
• In this reaction, intermediate is three membered cyclic oxonium ion (epoxide formation), this cyclic strain will be revealed by the attack of nucleophile (water) molecule.

To find: the structure of ${\text{C}}_{\text{6}}{\text{H}}_{\text{12}}$, which gives meso product with two chiral centers during anti-hydroxylation reaction.