Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)
Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)
2nd Edition
ISBN: 9780393655551
Author: KARTY, Joel
Publisher: W. W. Norton & Company
Question
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Chapter 19, Problem 19.14P
Interpretation Introduction

(a)

Interpretation:

To find out which reduction reaction can be used to carry out the transformation among the Wolff-kishner, Clemmensen, or Raney-nickel.

Concept introduction:

The Wolff-Kishner reduction is used to convert the carbonyl (C=O) group of a ketone or aldehyde into a CH2 group. The Clemmensen reduction is also used to reduce the C=O group of a ketone or aldehyde. The Raney-nickel reduction is used to reduce the carbonyl group of a ketone or aldehyde to a methylene group. The Wolff-Kishner reduction should be avoided if there is a functional group present that is susceptible to reaction under basic conditions or with strong nucleophiles. The Raney-nickel reduction should be avoided if there is a functional group present that is susceptible to reaction with nucleophilic thiols or with H2 in the presence of a metal catalyst.

Interpretation Introduction

(b)

Interpretation:

To find out which reduction reaction can be used to carry out the transformation among the Wolff-kishner, Clemmensen, or Raney-nickel.

Concept introduction:

The Wolff-Kishner reduction is used to convert the carbonyl (C=O) group of a ketone or aldehyde into a CH2 group. The Clemmensen reduction is also used to reduce the C=O group of a ketone or aldehyde. The Raney-nickel reduction is used to reduce the carbonyl group of a ketone or aldehyde to a methylene group. The Wolff-Kishner reduction should be avoided if there is a functional group present that is susceptible to reaction under basic conditions or with strong nucleophiles. The Raney-nickel reduction should be avoided if there is a functional group present that is susceptible to reaction with nucleophilic thiols or with H2 in the presence of a metal catalyst.

Interpretation Introduction

(c)

Interpretation:

To find out which reduction reaction can be used to carry out the transformation among the Wolff-kishner, Clemmensen, or Raney-nickel.

Concept introduction:

The Wolff-Kishner reduction is used to convert the carbonyl (C=O) group of a ketone or aldehyde into a CH2 group. The Clemmensen reduction is also used to reduce the C=O group of a ketone or aldehyde. The Raney-nickel reduction is used to reduce the carbonyl group of a ketone or aldehyde to a methylene group. The Wolff-Kishner reduction should be avoided if there is a functional group present that is susceptible to reaction under basic conditions or with strong nucleophiles. The Raney-nickel reduction should be avoided if there is a functional group present that is susceptible to reaction with nucleophilic thiols or with H2 in the presence of a metal catalyst.

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Please answer the question and provide a detailed drawing of the structure. If there will not be a new C – C bond, then the box under the drawing area will be checked.  Will the following reaction make a molecule with a new C – C bond as its major product:  Draw the major organic product or products, if the reaction will work. Be sure you use wedge and dash bonds if necessary, for example to distinguish between major products with different stereochemistry.

Chapter 19 Solutions

Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)

Ch. 19 - Prob. 19.11PCh. 19 - Prob. 19.12PCh. 19 - Prob. 19.13PCh. 19 - Prob. 19.14PCh. 19 - Prob. 19.15PCh. 19 - Prob. 19.16PCh. 19 - Prob. 19.17PCh. 19 - Prob. 19.18PCh. 19 - Prob. 19.19PCh. 19 - Prob. 19.20PCh. 19 - Prob. 19.21PCh. 19 - Prob. 19.22PCh. 19 - Prob. 19.23PCh. 19 - Prob. 19.24PCh. 19 - Prob. 19.25PCh. 19 - Prob. 19.26PCh. 19 - Prob. 19.27PCh. 19 - Prob. 19.28PCh. 19 - Prob. 19.29PCh. 19 - Prob. 19.30PCh. 19 - Prob. 19.31PCh. 19 - Prob. 19.32PCh. 19 - Prob. 19.33PCh. 19 - Prob. 19.34PCh. 19 - Prob. 19.35PCh. 19 - Prob. 19.36PCh. 19 - Prob. 19.37PCh. 19 - Prob. 19.38PCh. 19 - Prob. 19.39PCh. 19 - Prob. 19.40PCh. 19 - Prob. 19.41PCh. 19 - Prob. 19.42PCh. 19 - Prob. 19.43PCh. 19 - Prob. 19.44PCh. 19 - Prob. 19.45PCh. 19 - Prob. 19.46PCh. 19 - Prob. 19.47PCh. 19 - Prob. 19.48PCh. 19 - Prob. 19.49PCh. 19 - Prob. 19.50PCh. 19 - Prob. 19.51PCh. 19 - Prob. 19.52PCh. 19 - Prob. 19.53PCh. 19 - Prob. 19.54PCh. 19 - Prob. 19.55PCh. 19 - Prob. 19.56PCh. 19 - Prob. 19.57PCh. 19 - Prob. 19.58PCh. 19 - Prob. 19.59PCh. 19 - Prob. 19.60PCh. 19 - Prob. 19.61PCh. 19 - Prob. 19.62PCh. 19 - Prob. 19.63PCh. 19 - Prob. 19.64PCh. 19 - Prob. 19.65PCh. 19 - Prob. 19.66PCh. 19 - Prob. 19.67PCh. 19 - Prob. 19.68PCh. 19 - Prob. 19.69PCh. 19 - Prob. 19.70PCh. 19 - Prob. 19.71PCh. 19 - Prob. 19.72PCh. 19 - Prob. 19.73PCh. 19 - Prob. 19.74PCh. 19 - Prob. 19.75PCh. 19 - Prob. 19.76PCh. 19 - Prob. 19.77PCh. 19 - Prob. 19.78PCh. 19 - Prob. 19.79PCh. 19 - Prob. 19.1YTCh. 19 - Prob. 19.2YTCh. 19 - Prob. 19.3YTCh. 19 - Prob. 19.4YTCh. 19 - Prob. 19.5YTCh. 19 - Prob. 19.6YTCh. 19 - Prob. 19.7YTCh. 19 - Prob. 19.8YTCh. 19 - Prob. 19.9YTCh. 19 - Prob. 19.10YT
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