Organic Chemistry
Organic Chemistry
3rd Edition
ISBN: 9781119338352
Author: Klein
Publisher: WILEY
Question
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Chapter 8.10, Problem 26ATS

(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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None

Chapter 8 Solutions

Organic Chemistry

Ch. 8.5 - Prob. 3LTSCh. 8.5 - Prob. 10PTSCh. 8.5 - Prob. 11ATSCh. 8.6 - Prob. 12CCCh. 8.6 - Prob. 13CCCh. 8.7 - Below are several examples of...Ch. 8.7 - Prob. 15CCCh. 8.7 - Prob. 4LTSCh. 8.7 - Prob. 16PTSCh. 8.7 - Prob. 17ATSCh. 8.8 - Prob. 5LTSCh. 8.8 - Prob. 18PTSCh. 8.8 - Prob. 19ATSCh. 8.9 - Prob. 20CCCh. 8.9 - Predict the major product(s) for the following...Ch. 8.9 - Prob. 21PTSCh. 8.9 - Prob. 22ATSCh. 8.9 - Prob. 23ATSCh. 8.10 - Prob. 7LTSCh. 8.10 - Prob. 24PTSCh. 8.10 - Prob. 25ATSCh. 8.10 - Prob. 26ATSCh. 8.11 - Prob. 27CCCh. 8.12 - Prob. 8LTSCh. 8.12 - Prob. 28PTSCh. 8.12 - Prob. 29PTSCh. 8.12 - Prob. 30ATSCh. 8.13 - Prob. 9LTSCh. 8.13 - Prob. 31PTSCh. 8.13 - Prob. 32ATSCh. 8.13 - Prob. 33ATSCh. 8.13 - Prob. 34ATSCh. 8.14 - Prob. 10LTSCh. 8.14 - Prob. 35PTSCh. 8.14 - Prob. 36ATSCh. 8.14 - Prob. 11LTSCh. 8.14 - Prob. 37PTSCh. 8.14 - Bioethanol, ethanol produced by fermentation of...Ch. 8.14 - Prob. 12LTSCh. 8.14 - Prob. 39PTSCh. 8.14 - Prob. 40ATSCh. 8 - Prob. 41PPCh. 8 - Prob. 42PPCh. 8 - Prob. 43PPCh. 8 - Prob. 44PPCh. 8 - Prob. 45PPCh. 8 - Prob. 46PPCh. 8 - Prob. 47PPCh. 8 - Prob. 48PPCh. 8 - Prob. 49PPCh. 8 - Prob. 50PPCh. 8 - Prob. 51PPCh. 8 - Prob. 52PPCh. 8 - Prob. 53PPCh. 8 - Prob. 54PPCh. 8 - Prob. 55PPCh. 8 - Prob. 56PPCh. 8 - Prob. 57PPCh. 8 - Prob. 58PPCh. 8 - Prob. 59PPCh. 8 - Prob. 60PPCh. 8 - Prob. 61PPCh. 8 - Prob. 62PPCh. 8 - Prob. 63PPCh. 8 - Prob. 64PPCh. 8 - Prob. 65PPCh. 8 - Prob. 66PPCh. 8 - Prob. 67PPCh. 8 - Prob. 68PPCh. 8 - Prob. 69PPCh. 8 - Prob. 70PPCh. 8 - Prob. 71PPCh. 8 - Prob. 72PPCh. 8 - Prob. 73PPCh. 8 - Prob. 74IPCh. 8 - Prob. 75IPCh. 8 - Prob. 76IPCh. 8 - Prob. 77IPCh. 8 - Prob. 78IPCh. 8 - Prob. 79IPCh. 8 - Prob. 80IPCh. 8 - Prob. 81IPCh. 8 - Prob. 82IPCh. 8 - Prob. 83IPCh. 8 - Prob. 84IPCh. 8 - Prob. 85IPCh. 8 - Prob. 86IPCh. 8 - Prob. 87IPCh. 8 - Prob. 88IPCh. 8 - Prob. 90IPCh. 8 - Prob. 91IPCh. 8 - Prob. 92IPCh. 8 - Prob. 93CPCh. 8 - Prob. 95CPCh. 8 - Prob. 96CP
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