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 C 6 H 12 , which gives non-chiral product during anti-hydroxylation reaction.

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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 C6H12 , 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 C6H12 , which gives meso product with two chiral centers during anti-hydroxylation reaction.

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