EBK ORGANIC CHEMISTRY-PRINT COMPANION (
EBK ORGANIC CHEMISTRY-PRINT COMPANION (
4th Edition
ISBN: 9781119776741
Author: Klein
Publisher: WILEY CONS
Question
Book Icon
Chapter 21.5, Problem 34ATS
Interpretation Introduction

Interpretation:

To draw the product when 1,4-dibromobutane undergoes acetoacetic ester synthesis

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,

EBK ORGANIC CHEMISTRY-PRINT COMPANION (, Chapter 21.5, Problem 34ATS , additional homework tip  1

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

EBK ORGANIC CHEMISTRY-PRINT COMPANION (, Chapter 21.5, Problem 34ATS , additional homework tip  2

Steps involved in malonic ester synthesis are,

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

To draw : To draw the structure of product when 1,4-dibromobutane is subjected to malonic ester synthesis.

Blurred answer

Chapter 21 Solutions

EBK ORGANIC CHEMISTRY-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. 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
Knowledge Booster
Background pattern image
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