Organic Chemistry, Binder Ready Version
Organic Chemistry, Binder Ready Version
2nd Edition
ISBN: 9781118454312
Author: David R. Klein
Publisher: WILEY
Question
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Chapter 22.5, Problem 36ATS

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using malonic ester synthesis starting 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, Binder Ready Version, Chapter 22.5, Problem 36ATS , 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, Binder Ready Version, Chapter 22.5, Problem 36ATS , 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

The formed carboxylic acid can be converted into carboxylic acid derivatives by reaction with respective reagents,

  • Ester=carboxylic acid + alcohol
  • Alchol=reduction of carboxylic acid
  • Amide=Reaction with ammonia

To describe : To describe how the given compound can be synthesized using diethyl malonate and other reagent.

(b)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using malonic ester synthesis starting 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, Binder Ready Version, Chapter 22.5, Problem 36ATS , 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, Binder Ready Version, Chapter 22.5, Problem 36ATS , 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

The formed carboxylic acid can be converted into carboxylic acid derivatives by reaction with respective reagents,

  • Ester=carboxylic acid + alcohol
  • Alchol=reduction of carboxylic acid
  • Amide=Reaction with ammonia

To describe : To describe how the given compound can be synthesized using diethyl malonate and other reagent.

(c)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using malonic ester synthesis starting 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, Binder Ready Version, Chapter 22.5, Problem 36ATS , 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, Binder Ready Version, Chapter 22.5, Problem 36ATS , 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

The formed carboxylic acid can be converted into carboxylic acid derivatives by reaction with respective reagents,

  • Ester=carboxylic acid + alcohol
  • Alchol=reduction of carboxylic acid
  • Amide=Reaction with ammonia

To describe : To describe how the given compound can be synthesized using diethyl malonate and other reagent.

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Chapter 22 Solutions

Organic Chemistry, Binder Ready Version

Ch. 22.2 - Prob. 10CCCh. 22.2 - Prob. 11CCCh. 22.2 - Prob. 12CCCh. 22.2 - Prob. 13CCCh. 22.2 - Prob. 14CCCh. 22.3 - Prob. 2LTSCh. 22.3 - Prob. 15PTSCh. 22.3 - Prob. 16PTSCh. 22.3 - Prob. 17ATSCh. 22.3 - Prob. 18ATSCh. 22.3 - Prob. 19ATSCh. 22.3 - Prob. 3LTSCh. 22.3 - Prob. 20PTSCh. 22.3 - Prob. 21ATSCh. 22.3 - Prob. 22ATSCh. 22.3 - Prob. 4LTSCh. 22.3 - Prob. 23PTSCh. 22.3 - Prob. 24ATSCh. 22.3 - Prob. 25CCCh. 22.3 - Prob. 26CCCh. 22.3 - Prob. 27CCCh. 22.4 - Prob. 28CCCh. 22.4 - Prob. 29CCCh. 22.4 - Prob. 30CCCh. 22.4 - Prob. 31CCCh. 22.4 - Prob. 32CCCh. 22.5 - Prob. 33CCCh. 22.5 - Prob. 34CCCh. 22.5 - Prob. 5LTSCh. 22.5 - Prob. 35PTSCh. 22.5 - Prob. 36ATSCh. 22.5 - Prob. 37ATSCh. 22.5 - Prob. 38ATSCh. 22.5 - Prob. 6LTSCh. 22.5 - Prob. 39PTSCh. 22.5 - Prob. 40ATSCh. 22.5 - Prob. 41ATSCh. 22.5 - Prob. 42ATSCh. 22.5 - Prob. 43ATSCh. 22.6 - Prob. 44CCCh. 22.6 - Prob. 45CCCh. 22.6 - Prob. 46CCCh. 22.6 - Prob. 7LTSCh. 22.6 - Prob. 47PTSCh. 22.6 - Prob. 48ATSCh. 22.6 - Prob. 49CCCh. 22.6 - Prob. 50CCCh. 22.7 - Prob. 8LTSCh. 22.7 - Prob. 51PTSCh. 22.7 - Prob. 52PTSCh. 22.7 - Prob. 53ATSCh. 22.7 - Prob. 9LTSCh. 22.7 - Prob. 54PTSCh. 22.7 - Prob. 55ATSCh. 22.7 - Prob. 56ATSCh. 22 - Prob. 57PPCh. 22 - Prob. 58PPCh. 22 - Prob. 59PPCh. 22 - Prob. 60PPCh. 22 - Prob. 61PPCh. 22 - Prob. 62PPCh. 22 - Prob. 63PPCh. 22 - Prob. 64PPCh. 22 - Prob. 65PPCh. 22 - Prob. 66PPCh. 22 - Prob. 67PPCh. 22 - Prob. 68PPCh. 22 - Prob. 69PPCh. 22 - Prob. 70PPCh. 22 - Prob. 71PPCh. 22 - Prob. 72PPCh. 22 - Prob. 73PPCh. 22 - Prob. 74PPCh. 22 - Prob. 75PPCh. 22 - Prob. 76PPCh. 22 - Prob. 77PPCh. 22 - Prob. 78PPCh. 22 - Prob. 79PPCh. 22 - Prob. 80PPCh. 22 - Prob. 81PPCh. 22 - Prob. 82PPCh. 22 - Prob. 83PPCh. 22 - Prob. 84PPCh. 22 - Prob. 85PPCh. 22 - Prob. 86PPCh. 22 - Prob. 87PPCh. 22 - Prob. 88PPCh. 22 - Prob. 89PPCh. 22 - Prob. 90PPCh. 22 - Prob. 91PPCh. 22 - Prob. 92PPCh. 22 - Prob. 93PPCh. 22 - Prob. 94PPCh. 22 - Prob. 95PPCh. 22 - Prob. 96PPCh. 22 - Prob. 97PPCh. 22 - Prob. 98PPCh. 22 - Prob. 99PPCh. 22 - Prob. 100IPCh. 22 - Prob. 101IPCh. 22 - Prob. 102IPCh. 22 - Prob. 103IPCh. 22 - Prob. 104IPCh. 22 - Prob. 105IPCh. 22 - Prob. 106IPCh. 22 - Prob. 107IPCh. 22 - Prob. 108IPCh. 22 - Prob. 109IPCh. 22 - Prob. 110IPCh. 22 - Prob. 111IPCh. 22 - Prob. 112IP
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