Organic Chemistry, Binder Ready Version
Organic Chemistry, Binder Ready Version
2nd Edition
ISBN: 9781118454312
Author: David R. Klein
Publisher: WILEY
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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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Organic Chemistry, Binder Ready Version

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