Organic Chemistry, Third Edition Binder Ready Version
Organic Chemistry, Third Edition Binder Ready Version
3rd Edition
ISBN: 9781119110453
Author: Klein
Publisher: WILEY
Question
Book Icon
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, Third Edition Binder Ready Version, 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, Third Edition Binder Ready Version, 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, Third Edition Binder Ready Version, 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, Third Edition Binder Ready Version, 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, Third Edition Binder Ready Version, 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, Third Edition Binder Ready Version, 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, Third Edition Binder Ready Version, 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, Third Edition Binder Ready Version, 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

Blurred answer
Students have asked these similar questions
Record the amounts measured and calculate the percent yield for Part 2 in the table below. Dicyclopentadiene measured in volume Cyclopentadiene measured in grams 0 Measured Calculated Mol Yield Mass (g) or Volume (mL) Mass (g) or Volume (ml) 0.6 2.955 Part 2 Measurements and Results Record the amounts measured and calculate the percent yield for Part 2 in the table below. 0.588 0.0044 2.868 0.0434 N/A Table view List view Measured Calculated Mol $ Yield Melting Point (C) Mass (g) or Volume (ml) Mass (g) or Volume (ml.) Cyclopentadiene 0.1 0.08 0.001189 measured in volume Maleic Anhydride 0.196 N/A cis-norbornene-5,6-endo- dicarboxylic anhydride 0.041 0.0002467 N/A N/A N/A 0.002 N/A N/A 128
Draw the condensed structural formula and line-angle formula for each: 2,3-dimethylheptane 3-bromo-2-pentanol 3-isopropyl-2-hexene 4-chlorobutanoic acid
Record the IUPAC names for each of the structures shown below. a) b) c) OH d) OH e)

Chapter 21 Solutions

Organic Chemistry, Third Edition Binder Ready Version

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
Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Text book image
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Text book image
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Text book image
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Text book image
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY