Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
Question
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Chapter 9.2, Problem 10P

(a)

Interpretation Introduction

Interpretation:

From the given species stronger base has to be identified.

Concept Introduction:

  • Aprotic solvent are polar solvent molecules which do not have hydrogen bonded to oxygen to nitrogen.
  • Protic solvent are polar solvent molecules which do have hydrogen bonded to oxygen to nitrogen.
  • The stronger base is always a better nucleophile in an aprotic solvent.

(b)

Interpretation Introduction

Interpretation:

The better nucleophile in aqueous solution has to be identified.

Concept Introduction:

  • Aprotic solvent are polar solvent molecules which do not have hydrogen bonded to oxygen to nitrogen.
  • Protic solvent are polar solvent molecules which do have hydrogen bonded to oxygen to nitrogen.
  • The stronger base is always a better nucleophile in an aprotic solvent.

(c)

Interpretation Introduction

Interpretation:

The better nucleophile in DMSO solution has to be identified.

Concept Introduction:

  • Aprotic solvent are polar solvent molecules which do not have hydrogen bonded to oxygen to nitrogen.
  • Protic solvent are polar solvent molecules which do have hydrogen bonded to oxygen to nitrogen
  • The stronger base is always a better nucleophile in an aprotic solvent.

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4. Provide a clear arrow-pushing mechanism for each of the following reactions. Do not skip proton transfers, do not combine steps, and make sure your arrows are clear enough to be interpreted without ambiguity. a. 2. 1. LDA 3. H3O+ HO
b. H3C CH3 H3O+ ✓ H OH
2. Provide reagents/conditions to accomplish the following syntheses. More than one step is required in some cases. a. CH3

Chapter 9 Solutions

Organic Chemistry

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