ORGANIC CHEMISTRY (LL)-W/WILEYPLUS
ORGANIC CHEMISTRY (LL)-W/WILEYPLUS
4th Edition
ISBN: 9781119659556
Author: Klein
Publisher: WILEY
Question
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Chapter 21.5, Problem 33PTS

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using acetoacetic ester synthesis

Concept introduction:

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

ORGANIC CHEMISTRY (LL)-W/WILEYPLUS, Chapter 21.5, Problem 33PTS , additional homework tip  1

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

ORGANIC CHEMISTRY (LL)-W/WILEYPLUS, Chapter 21.5, Problem 33PTS , 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

(b)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using acetoacetic ester synthesis

Concept introduction:

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

ORGANIC CHEMISTRY (LL)-W/WILEYPLUS, Chapter 21.5, Problem 33PTS , additional homework tip  3

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

ORGANIC CHEMISTRY (LL)-W/WILEYPLUS, Chapter 21.5, Problem 33PTS , 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

(c)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using acetoacetic ester synthesis

Concept introduction:

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

ORGANIC CHEMISTRY (LL)-W/WILEYPLUS, Chapter 21.5, Problem 33PTS , additional homework tip  5

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

ORGANIC CHEMISTRY (LL)-W/WILEYPLUS, Chapter 21.5, Problem 33PTS , 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

(d)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using acetoacetic ester synthesis

Concept introduction:

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

ORGANIC CHEMISTRY (LL)-W/WILEYPLUS, Chapter 21.5, Problem 33PTS , additional homework tip  7

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

ORGANIC CHEMISTRY (LL)-W/WILEYPLUS, Chapter 21.5, Problem 33PTS , additional homework tip  8

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

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> You are trying to decide if there is a single reagent you can add that will make the following synthesis possible without any other major side products: 1. ☑ CI 2. H3O+ O Draw the missing reagent X you think will make this synthesis work in the drawing area below. If there is no reagent that will make your desired product in good yield or without complications, just check the box under the drawing area and leave it blank. Click and drag to start drawing a structure. Explanation Check ? DO 18 Ar B © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Accessibility
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Chapter 21 Solutions

ORGANIC CHEMISTRY (LL)-W/WILEYPLUS

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. 3LTSCh. 21.3 - Prob. 4LTSCh. 21.3 - Prob. 19PTSCh. 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. 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. 21.7 - Prob. 8LTSCh. 21.7 - Prob. 42PTSCh. 21.7 - Prob. 43PTSCh. 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. 97IPCh. 21 - Prob. 98IPCh. 21 - Prob. 99IPCh. 21 - Prob. 100IPCh. 21 - Prob. 101IPCh. 21 - Prob. 107IPCh. 21 - Prob. 108IPCh. 21 - Prob. 109IP
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