Organic Chemistry
Organic Chemistry
3rd Edition
ISBN: 9781119338352
Author: Klein
Publisher: WILEY
Question
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Chapter 21, Problem 68PP

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared from diethyl malonate and other reagents.

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic ester).  By use of this method two new alkyl groups can be introduced.  A general scheme of this synthesis is shown below,

Organic Chemistry, Chapter 21, Problem 68PP , additional homework tip  1

Please do remember that if alkyldihalide is used for malonic ester synthesis a cyclic product is expected. (Intramolecular malonic ester synthesis)

Organic Chemistry, Chapter 21, Problem 68PP , additional homework tip  2

Steps involved in malonic ester synthesis are,

  • Deprotonation of α carbon in malonic acid ester
  • Alkylation of enolate
  • Hydrolysis of ester using aqueous acid
  • Decarboxylation at high temperature

(b)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared from diethyl malonate and other reagents.

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic ester).  By use of this method two new alkyl groups can be introduced.  A general scheme of this synthesis is shown below,

Organic Chemistry, Chapter 21, Problem 68PP , additional homework tip  3

Please do remember that if alkyldihalide is used for malonic ester synthesis a cyclic product is expected. (Intramolecular malonic ester synthesis)

Organic Chemistry, Chapter 21, Problem 68PP , additional homework tip  4

Steps involved in malonic ester synthesis are,

  • Deprotonation of α carbon in malonic acid ester
  • Alkylation of enolate
  • Hydrolysis of ester using aqueous acid
  • Decarboxylation at high temperature

(c)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared from diethyl malonate and other reagents.

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic ester).  By use of this method two new alkyl groups can be introduced.  A general scheme of this synthesis is shown below,

Organic Chemistry, Chapter 21, Problem 68PP , additional homework tip  5

Please do remember that if alkyldihalide is used for malonic ester synthesis a cyclic product is expected. (Intramolecular malonic ester synthesis)

Organic Chemistry, Chapter 21, Problem 68PP , additional homework tip  6

Steps involved in malonic ester synthesis are,

  • Deprotonation of α carbon in malonic acid ester
  • Alkylation of enolate
  • Hydrolysis of ester using aqueous acid
  • Decarboxylation at high temperature

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Chapter 21 Solutions

Organic Chemistry

Ch. 21.2 - Prob. 10CCCh. 21.2 - Prob. 11CCCh. 21.2 - Prob. 12CCCh. 21.2 - Prob. 13CCCh. 21.3 - Prob. 2LTSCh. 21.3 - Prob. 14PTSCh. 21.3 - Prob. 15PTSCh. 21.3 - Prob. 16ATSCh. 21.3 - Prob. 3LTSCh. 21.3 - Prob. 17PTSCh. 21.3 - Prob. 18ATSCh. 21.3 - Prob. 4LTSCh. 21.3 - Prob. 19PTSCh. 21.3 - Prob. 20ATSCh. 21.3 - Prob. 21CCCh. 21.3 - Prob. 22CCCh. 21.3 - Prob. 23CCCh. 21.4 - Prob. 24CCCh. 21.4 - Prob. 25CCCh. 21.4 - Prob. 26CCCh. 21.4 - Prob. 27CCCh. 21.4 - Prob. 28CCCh. 21.5 - Prob. 29CCCh. 21.5 - Prob. 30CCCh. 21.5 - Prob. 5LTSCh. 21.5 - Prob. 31PTSCh. 21.5 - Prob. 32ATSCh. 21.5 - Prob. 6LTSCh. 21.5 - Prob. 33PTSCh. 21.5 - Prob. 34ATSCh. 21.6 - Prob. 35CCCh. 21.6 - Prob. 36CCCh. 21.6 - Prob. 37CCCh. 21.6 - Prob. 7LTSCh. 21.6 - Prob. 38PTSCh. 21.6 - Prob. 39ATSCh. 21.6 - Prob. 40CCCh. 21.6 - Prob. 41CCCh. 21.7 - Prob. 8LTSCh. 21.7 - Prob. 42PTSCh. 21.7 - Prob. 43PTSCh. 21.7 - Prob. 9LTSCh. 21.7 - Prob. 45PTSCh. 21.7 - Prob. 46ATSCh. 21 - Prob. 47PPCh. 21 - Prob. 48PPCh. 21 - Prob. 49PPCh. 21 - Prob. 50PPCh. 21 - Prob. 51PPCh. 21 - Prob. 52PPCh. 21 - Prob. 53PPCh. 21 - Prob. 54PPCh. 21 - Prob. 55PPCh. 21 - Prob. 56PPCh. 21 - Prob. 57PPCh. 21 - Prob. 58PPCh. 21 - Prob. 59PPCh. 21 - Prob. 60PPCh. 21 - Prob. 61PPCh. 21 - Prob. 62PPCh. 21 - Prob. 63PPCh. 21 - Prob. 64PPCh. 21 - Prob. 65PPCh. 21 - Prob. 66PPCh. 21 - Prob. 67PPCh. 21 - Prob. 68PPCh. 21 - Prob. 69PPCh. 21 - Prob. 70PPCh. 21 - Prob. 71PPCh. 21 - Prob. 72PPCh. 21 - Prob. 73PPCh. 21 - Prob. 74PPCh. 21 - Prob. 75PPCh. 21 - Prob. 76PPCh. 21 - Prob. 77PPCh. 21 - Prob. 78PPCh. 21 - Prob. 79PPCh. 21 - Prob. 80PPCh. 21 - Prob. 81PPCh. 21 - Prob. 82PPCh. 21 - Prob. 83PPCh. 21 - Prob. 84PPCh. 21 - Prob. 85PPCh. 21 - Prob. 86PPCh. 21 - Prob. 87PPCh. 21 - Prob. 88PPCh. 21 - Prob. 89IPCh. 21 - Prob. 90IPCh. 21 - Prob. 91IPCh. 21 - Prob. 92IPCh. 21 - Prob. 93IPCh. 21 - Prob. 94IPCh. 21 - Prob. 95IPCh. 21 - Prob. 96IPCh. 21 - Prob. 97IPCh. 21 - Prob. 98IPCh. 21 - Prob. 99IPCh. 21 - Prob. 100IPCh. 21 - Prob. 101IPCh. 21 - Prob. 102IPCh. 21 - Prob. 103IPCh. 21 - Prob. 104IPCh. 21 - Prob. 105IPCh. 21 - Prob. 106IPCh. 21 - Prob. 107IPCh. 21 - Prob. 108IPCh. 21 - Prob. 109IPCh. 21 - Prob. 110IPCh. 21 - Prob. 111IPCh. 21 - Prob. 112IPCh. 21 - Prob. 113IPCh. 21 - Prob. 114IPCh. 21 - Prob. 115IPCh. 21 - Prob. 116CPCh. 21 - Prob. 117CPCh. 21 - Prob. 118CP
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