Organic Chemistry, Third Edition Binder Ready Version
Organic Chemistry, Third Edition Binder Ready Version
3rd Edition
ISBN: 9781119110453
Author: Klein
Publisher: WILEY
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Chapter 8.6, Problem 13CC

(a)

Interpretation Introduction

Interpretation:

The product of given oxymercuration-demercuration has to be identified.

Concept Introduction:

  • Oxymercuration-Demercuration:  In this reaction, alkene undergoes oxymercuration to form mercurinium ion intermediate.  This intermediate reacts with nucleophile and mercury can be removed by sodium borohydride.

    Organic Chemistry, Third Edition Binder Ready Version, Chapter 8.6, Problem 13CC , additional homework tip  1

  • The intermediate (mercurinium ion) obtained in this reaction does not undergo rearrangement because of partial positive charge on more substituted carbon.  Hence, the product is obtained without any rearrangement.

    Organic Chemistry, Third Edition Binder Ready Version, Chapter 8.6, Problem 13CC , additional homework tip  2

(b)

Interpretation Introduction

Interpretation:

The product of given oxymercuration-demercuration has to be identified.

Concept Introduction:

  • Oxymercuration-Demercuration:  In this reaction, alkene undergoes oxymercuration to form mercurinium ion intermediate.  This intermediate reacts with nucleophile and mercury can be removed by sodium borohydride.

    Organic Chemistry, Third Edition Binder Ready Version, Chapter 8.6, Problem 13CC , additional homework tip  3

  • The intermediate (mercurinium ion) obtained in this reaction does not undergo rearrangement because of partial positive charge on more substituted carbon.  Hence, the product is obtained without any rearrangement.

    Organic Chemistry, Third Edition Binder Ready Version, Chapter 8.6, Problem 13CC , additional homework tip  4

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Chapter 8 Solutions

Organic Chemistry, Third Edition Binder Ready Version

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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