ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY
ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY
4th Edition
ISBN: 9781119761105
Author: Klein
Publisher: WILEY
Question
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Chapter 21.5, Problem 31PTS

(a)

Interpretation Introduction

Interpretation:

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

Concept introduction:

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

ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY, Chapter 21.5, Problem 31PTS , additional homework tip  1

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

ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY, Chapter 21.5, Problem 31PTS , additional homework tip  2

Steps involved in malonic ester synthesis are,

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

To describe : To describe how the given compound can be synthesized using malonic ester synthesis.

(b)

Interpretation Introduction

Interpretation:

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

Concept introduction:

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

ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY, Chapter 21.5, Problem 31PTS , additional homework tip  3

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

ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY, Chapter 21.5, Problem 31PTS , additional homework tip  4

Steps involved in malonic ester synthesis are,

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

To describe : To describe how the given compound can be synthesized using malonic ester synthesis.

(c)

Interpretation Introduction

Interpretation:

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

Concept introduction:

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

ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY, Chapter 21.5, Problem 31PTS , additional homework tip  5

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

ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY, Chapter 21.5, Problem 31PTS , additional homework tip  6

Steps involved in malonic ester synthesis are,

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

To describe : To describe how the given compound can be synthesized using malonic ester synthesis.

(d)

Interpretation Introduction

Interpretation:

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

Concept introduction:

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

ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY, Chapter 21.5, Problem 31PTS , additional homework tip  7

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

ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY, Chapter 21.5, Problem 31PTS , additional homework tip  8

Steps involved in malonic ester synthesis are,

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

To describe : To describe how the given compound can be synthesized using malonic ester synthesis.

(e)

Interpretation Introduction

Interpretation:

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

Concept introduction:

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

ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY, Chapter 21.5, Problem 31PTS , additional homework tip  9

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

ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY, Chapter 21.5, Problem 31PTS , additional homework tip  10

Steps involved in malonic ester synthesis are,

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

To describe : To describe how the given compound can be synthesized using malonic ester synthesis.

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Students have asked these similar questions
3. Propose a synthesis for the following transformation. Do not draw an arrow-pushing mechanism below, but make sure to draw the product of each proposed step (3 points). CN + En CN
3) Propagation of uncertainty. Every measurement has uncertainty. In this problem, we'll evaluate the uncertainty in every step of a titration of potassium hydrogen phthalate (a common acid used in titrations, abbreviated KHP, formula CsH5KO4) with NaOH of an unknown concentration. The calculation that ultimately needs to be carried out is: concentration NaOH 1000 x mass KHP × purity KHP molar mass KHP x volume NaOH Measurements: a) You use a balance to weigh 0.3992 g of KHP. The uncertainty is ±0.15 mg (0.00015 g). b) You use a buret to slowly add NaOH to the KHP until it reaches the endpoint. It takes 18.73 mL of NaOH. The uncertainty of the burst is 0.03 mL.. c) The manufacturer states the purity of KHP is 100%±0.05%. d) Even though we don't think much about them, molar masses have uncertainty as well. The uncertainty comes from the distribution of isotopes, rather than random measurement error. The uncertainty in the elements composing KHP are: a. Carbon: b. Hydrogen: ±0.0008…
Don't used hand raiting and don't used Ai solution

Chapter 21 Solutions

ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY

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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