EBK ESSENTIAL ORGANIC CHEMISTRY
EBK ESSENTIAL ORGANIC CHEMISTRY
3rd Edition
ISBN: 8220100659461
Author: Bruice
Publisher: PEARSON
Question
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Chapter 12.10, Problem 26P

(a)

Interpretation Introduction

Interpretation: The major product of the given reaction has to be identified.

Concept Introduction:

Major product in the reaction of α,β- unsaturated carbonyl compounds with weak bases:

α,β- Unsaturated carbonyl compounds on reaction with weak bases gives conjugate addition products as the major products as shown in the following general scheme:

General scheme:

  EBK ESSENTIAL ORGANIC CHEMISTRY, Chapter 12.10, Problem 26P , additional homework tip  1

It can be observed that the conjugate addition product has been formed by the addition of basic anion to the beta-carbon atom and that of hydrogen atom to the alpha-carbon carbon atom.

The examples for the weak bases are:

  HBrCH3SHCH3OHNH3

(b)

Interpretation Introduction

Interpretation: The major product of the given reaction has to be found.

Concept Introduction:

Major product in the reaction of α,β- unsaturated carbonyl compounds with strong bases:

α,β- Unsaturated carbonyl compounds on reaction with strong bases gives direct addition products as the major products as shown in the following general scheme:

General scheme:

EBK ESSENTIAL ORGANIC CHEMISTRY, Chapter 12.10, Problem 26P , additional homework tip  2

It can be observed that the direct addition product has been formed from the direct reaction of the strong base with the carbonyl functional group of the α,β- unsaturated carbonyl compounds.

The examples for the strong bases are:

CH3Mg2+BrGignardreagentNaBH4H-hydridedonor

(c)

Interpretation Introduction

Interpretation: The major product of the given reaction has to be found.

Concept Introduction:

Major product in the reaction of α,β- unsaturated carbonyl compounds with weak bases:

α,β- Unsaturated carbonyl compounds on reaction with weak bases gives conjugate addition products as the major products as shown in the following general scheme:

General scheme:

EBK ESSENTIAL ORGANIC CHEMISTRY, Chapter 12.10, Problem 26P , additional homework tip  3

It can be observed that the conjugate addition product has been formed by the addition of basic anion to the beta-carbon atom and that of hydrogen atom to the alpha-carbon carbon atom.

The examples for the weak bases are:

HBrCH3SHCH3OHNH3

(d)

Interpretation Introduction

Interpretation: The major product of the given reaction has to be found.

Concept Introduction:

Major product in the reaction of α,β- unsaturated carbonyl compounds with strong bases:

α,β- Unsaturated carbonyl compounds on reaction with strong bases gives direct addition products as the major products as shown in the following general scheme:

General scheme:

EBK ESSENTIAL ORGANIC CHEMISTRY, Chapter 12.10, Problem 26P , additional homework tip  4

It can be observed that the direct addition product has been formed from the direct reaction of the strong base with the carbonyl functional group of the α,β- unsaturated carbonyl compounds.

The examples for the strong bases are:

CH3Mg2+BrGignardreagentNaBH4H-hydridedonor

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Done 11:14 ⚫ worksheets.beyondlabz.com 5 (a). Using the peak information you listed in the tables for both structures, assign each peak to that portion of the structure that produces the peak in the NMR spectrum. Draw this diagram on your own sheet of paper and attach the sketch of your drawing to this question. Question 6 5 (b). Using the peak information you listed in the tables for both structures, assign each peak to that portion of the structure that produces the peak in the NMR spectrum. Draw this diagram on your own sheet of paper and attach the sketch of your drawing to this question. Question 7 6. Are there any differences between the spectra you obtained in Beyond Labz and the predicted spectra? If so, what were the differences? <
2. Predict the NMR spectra for each of these two compounds by listing, in the NMR tables below, the chemical shift, the splitting, and the number of hydrogens associated with each predicted peak. Sort the peaks from largest chemical shift to lowest. **Not all slots must be filled** Peak Chemical Shift (d) 5.7 1 Multiplicity multiplate .......... 5.04 double of doublet 2 4.98 double of doublet 3 4.05 doublet of quartet 4 5 LO 3.80 quartet 1.3 doublet 6 Peak Chemical Shift (d) Multiplicity
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