ORGANIC CHEMISTRY, WITH SOL. MAN/ STUDY
ORGANIC CHEMISTRY, WITH SOL. MAN/ STUDY
3rd Edition
ISBN: 9781119477617
Author: Klein
Publisher: WILEY
Question
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Chapter 8.6, Problem 12CC

(a)

Interpretation Introduction

Interpretation:

The products of acid-catalysed hydration and oxymercuration-demercuration of given reactants have to be identified.

Concept Introduction:

  • Simple hydration in acidic media gives the addition product through carbocation intermediate and follows Markovnikov’s addition.
  • An acid-catalysed hydration is shown below.

    ORGANIC CHEMISTRY, WITH SOL. MAN/ STUDY, Chapter 8.6, Problem 12CC , additional homework tip  1

  • Markovnikov’s rule: An unsymmetrical alkene reacts with hydrogen halide in which halide ions goes to the more substitution position of carbon-carbon double bond which provides alkyl halides.

ORGANIC CHEMISTRY, WITH SOL. MAN/ STUDY, Chapter 8.6, Problem 12CC , additional homework tip  2

  • 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, WITH SOL. MAN/ STUDY, Chapter 8.6, Problem 12CC , additional homework tip  3

(b)

Interpretation Introduction

Interpretation:

The products of acid-catalysed hydration and oxymercuration-demercuration of given reactants have to be identified.

Concept Introduction:

  • Simple hydration in acidic media gives the addition product through carbocation intermediate and follows Markovnikov’s addition.
  • An acid-catalysed hydration is shown below.

    ORGANIC CHEMISTRY, WITH SOL. MAN/ STUDY, Chapter 8.6, Problem 12CC , additional homework tip  4

  • Markovnikov’s rule: An unsymmetrical alkene reacts with hydrogen halide in which halide ions goes to the more substitution position of carbon-carbon double bond which provides alkyl halides.

ORGANIC CHEMISTRY, WITH SOL. MAN/ STUDY, Chapter 8.6, Problem 12CC , additional homework tip  5

  • 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, WITH SOL. MAN/ STUDY, Chapter 8.6, Problem 12CC , additional homework tip  6

(c)

Interpretation Introduction

Interpretation:

The products of acid-catalysed hydration and oxymercuration-demercuration of given reactants have to be identified.

Concept Introduction:

  • Simple hydration in acidic media gives the addition product through carbocation intermediate and follows Markovnikov’s addition.
  • An acid-catalysed hydration is shown below.

    ORGANIC CHEMISTRY, WITH SOL. MAN/ STUDY, Chapter 8.6, Problem 12CC , additional homework tip  7

  • Markovnikov’s rule: An unsymmetrical alkene reacts with hydrogen halide in which halide ions goes to the more substitution position of carbon-carbon double bond which provides alkyl halides.

ORGANIC CHEMISTRY, WITH SOL. MAN/ STUDY, Chapter 8.6, Problem 12CC , additional homework tip  8

  • 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, WITH SOL. MAN/ STUDY, Chapter 8.6, Problem 12CC , additional homework tip  9

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Chapter 8 Solutions

ORGANIC CHEMISTRY, WITH SOL. MAN/ STUDY

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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