ORG.CHEM EBOOK W/BBWILEY PLUS>CUSTOM<
ORG.CHEM EBOOK W/BBWILEY PLUS>CUSTOM<
2nd Edition
ISBN: 9781118872925
Author: Klein
Publisher: JOHN WILEY+SONS INC.CUSTOM
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Chapter 22.4, Problem 30CC

(a)

Interpretation Introduction

Interpretation:

To predict the reagent used for obtaining the given set of compounds synthesized by claisen condensation.

Concept introduction:

Claisen condensation is a process where a carbon-carbon bond is formed when reaction occurs between two esters or one ester and carbonyl compound in presence of a strong base to form a β -keto ester or a β -diketone, respectively

  • Deprotonation of α carbon to form ester enolate
  • Attach of enolate ion with the carbonyl of ester or ketone (nucleophilic attack)
  • Loss of alkoxide ion to reform carbonyl

ORG.CHEM EBOOK W/BBWILEY PLUS>CUSTOM<, Chapter 22.4, Problem 30CC , additional homework tip  1

Please note if the considered ester is of two different types then the reaction is known as crossed-claisen condensation.  LDA is used as a base in crossed claisen condensation.

To identify : The identify the reagent used for the given compound synthesized via claisen condensation

ORG.CHEM EBOOK W/BBWILEY PLUS>CUSTOM<, Chapter 22.4, Problem 30CC , additional homework tip  2

(b)

Interpretation Introduction

Interpretation:

To predict the reagent used for obtaining the given set of compounds synthesized by claisen condensation.

Concept introduction:

Claisen condensation is a process where a carbon-carbon bond is formed when reaction occurs between two esters or one ester and carbonyl compound in presence of a strong base to form a β -keto ester or a β -diketone, respectively

  • Deprotonation of α carbon to form ester enolate
  • Attach of enolate ion with the carbonyl of ester or ketone (nucleophilic attack)
  • Loss of alkoxide ion to reform carbonyl

ORG.CHEM EBOOK W/BBWILEY PLUS>CUSTOM<, Chapter 22.4, Problem 30CC , additional homework tip  3

Please note if the considered ester is of two different types then the reaction is known as crossed-claisen condensation.  LDA is used as a base in crossed claisen condensation.

To identify : The identify the reagent used for the given compound synthesized via claisen condensation

ORG.CHEM EBOOK W/BBWILEY PLUS>CUSTOM<, Chapter 22.4, Problem 30CC , additional homework tip  4

(c)

Interpretation Introduction

Interpretation:

To predict the reagent used for obtaining the given set of compounds synthesized by claisen condensation.

Concept introduction:

Claisen condensation is a process where a carbon-carbon bond is formed when reaction occurs between two esters or one ester and carbonyl compound in presence of a strong base to form a β -keto ester or a β -diketone, respectively

  • Deprotonation of α carbon to form ester enolate
  • Attach of enolate ion with the carbonyl of ester or ketone (nucleophilic attack)
  • Loss of alkoxide ion to reform carbonyl

ORG.CHEM EBOOK W/BBWILEY PLUS>CUSTOM<, Chapter 22.4, Problem 30CC , additional homework tip  5

Please note if the considered ester is of two different types then the reaction is known as crossed-claisen condensation.  LDA is used as a base in crossed claisen condensation.

To identify : The identify the reagent used for the given compound synthesized via claisen condensation

ORG.CHEM EBOOK W/BBWILEY PLUS>CUSTOM<, Chapter 22.4, Problem 30CC , additional homework tip  6

(d)

Interpretation Introduction

Interpretation:

To predict the reagent used for obtaining the given set of compounds synthesized by claisen condensation.

Concept introduction:

Claisen condensation is a process where a carbon-carbon bond is formed when reaction occurs between two esters or one ester and carbonyl compound in presence of a strong base to form a β -keto ester or a β -diketone, respectively

  • Deprotonation of α carbon to form ester enolate
  • Attach of enolate ion with the carbonyl of ester or ketone (nucleophilic attack)
  • Loss of alkoxide ion to reform carbonyl

ORG.CHEM EBOOK W/BBWILEY PLUS>CUSTOM<, Chapter 22.4, Problem 30CC , additional homework tip  7

Please note if the considered ester is of two different types then the reaction is known as crossed-claisen condensation.  LDA is used as a base in crossed claisen condensation.

To identify : The identify the reagent used for the given compound synthesized via claisen condensation

ORG.CHEM EBOOK W/BBWILEY PLUS>CUSTOM<, Chapter 22.4, Problem 30CC , additional homework tip  8

(e)

Interpretation Introduction

Interpretation:

To predict the reagent used for obtaining the given set of compounds synthesized by claisen condensation.

Concept introduction:

Claisen condensation is a process where a carbon-carbon bond is formed when reaction occurs between two esters or one ester and carbonyl compound in presence of a strong base to form a β -keto ester or a β -diketone, respectively

  • Deprotonation of α carbon to form ester enolate
  • Attach of enolate ion with the carbonyl of ester or ketone (nucleophilic attack)
  • Loss of alkoxide ion to reform carbonyl

ORG.CHEM EBOOK W/BBWILEY PLUS>CUSTOM<, Chapter 22.4, Problem 30CC , additional homework tip  9

Please note if the considered ester is of two different types then the reaction is known as crossed-claisen condensation.  LDA is used as a base in crossed claisen condensation.

To identify : The identify the reagent used for the given compound synthesized via claisen condensation

ORG.CHEM EBOOK W/BBWILEY PLUS>CUSTOM<, Chapter 22.4, Problem 30CC , additional homework tip  10

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Chapter 22 Solutions

ORG.CHEM EBOOK W/BBWILEY PLUS>CUSTOM<

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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