Organic Chemistry, 3e WileyPLUS Registration Card + Loose-leaf Print Companion
Organic Chemistry, 3e WileyPLUS Registration Card + Loose-leaf Print Companion
3rd Edition
ISBN: 9781119340577
Author: Klein
Publisher: Wiley (WileyPLUS Products)
Question
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Chapter 21, Problem 105IP

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using acetoacetic ester synthesis starting from ethyl acetoacetate and other reagents

Concept introduction:

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

Organic Chemistry, 3e WileyPLUS Registration Card + Loose-leaf Print Companion, Chapter 21, Problem 105IP , additional homework tip  1

Please do remember that if alkyldihalide is used for acetoacetic ester synthesis a cyclic product is expected.

Organic Chemistry, 3e WileyPLUS Registration Card + Loose-leaf Print Companion, Chapter 21, Problem 105IP , additional homework tip  2

Steps involved in acetoacetic ester synthesis are,

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

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

  • Acetal=ketone + diol
  • Alchol=reduction of ketone
  • Imine=Reaction with excess ammonia

To describe : To describe how the given compound can be synthesized using ethyl acetoacetate and other reagents.

(b)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using acetoacetic ester synthesis starting from ethyl acetoacetate and other reagents

Concept introduction:

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

Organic Chemistry, 3e WileyPLUS Registration Card + Loose-leaf Print Companion, Chapter 21, Problem 105IP , additional homework tip  3

Please do remember that if alkyldihalide is used for acetoacetic ester synthesis a cyclic product is expected.

Organic Chemistry, 3e WileyPLUS Registration Card + Loose-leaf Print Companion, Chapter 21, Problem 105IP , additional homework tip  4

Steps involved in acetoacetic ester synthesis are,

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

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

  • Acetal=ketone + diol
  • Alchol=reduction of ketone
  • Imine=Reaction with excess ammonia

To describe : To describe how the given compound can be synthesized using ethyl acetoacetate and other reagent.

(c)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using acetoacetic ester synthesis starting from ethyl acetoacetate and other reagents

Concept introduction:

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

Organic Chemistry, 3e WileyPLUS Registration Card + Loose-leaf Print Companion, Chapter 21, Problem 105IP , additional homework tip  5

Please do remember that if alkyldihalide is used for acetoacetic ester synthesis a cyclic product is expected.

Organic Chemistry, 3e WileyPLUS Registration Card + Loose-leaf Print Companion, Chapter 21, Problem 105IP , additional homework tip  6

Steps involved in acetoacetic ester synthesis are,

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

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

  • Acetal=ketone + diol
  • Alchol=reduction of ketone
  • Imine=Reaction with excess ammonia

To describe : To describe how the given compound can be synthesized using ethyl acetoacetate and other reagent.

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Chapter 21 Solutions

Organic Chemistry, 3e WileyPLUS Registration Card + Loose-leaf Print Companion

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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