Organic Chemistry: Principles And Mechanisms
Organic Chemistry: Principles And Mechanisms
2nd Edition
ISBN: 9780393630756
Author: KARTY, Joel
Publisher: W.w. Norton & Company,
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Chapter 19, Problem 19.44P
Interpretation Introduction

(a)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

The carbonyl groups of aldehyde or ketone can be reduced to methylene i.e. C=O to CH2 using the reactions like Wolff-Kishner reduction, Clemmensen reduction, and Raney-nickel reduction. Clemmensen reduction uses a zinc amalgam, which is an alloy (blend) of zinc with mercury. The ketone or aldehyde is refluxed (i.e., continuously evaporated and recondensed under heat) with the amalgam in concentrated HCl solution.

Interpretation Introduction

(b)

Interpretation:

The product of the given reaction is to be predicted

Concept introduction:

The carbonyl groups of aldehyde or ketone can be reduced to methylene i.e. C=O to CH2 using the reactions like Wolff-Kishner reduction, Clemmensen reduction, and Raney-nickel reduction. The reagent used for Wolff-Kishner reduction is NH2NH2, NaOH, H2O,Δ.

Interpretation Introduction

(c)

Interpretation: The product of the given reaction is to be predicted

Concept introduction:

The carbonyl groups of aldehyde or ketone can be reduced to methylene i.e. C=O to CH2 using reactions like Wolff-Kishner reduction, Clemmensen reduction, and Raney-nickel reduction. In a Raney-nickel reduction, the ketone or aldehyde is first converted to a thioacetal by treatment with a thiol under acidic conditions. Subsequent treatment with Raney nickel converts the thioacetal group to a methylene group.

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Shown below is the mechanism presented for the formation of biasplatin in reference 1 from the Background and Experiment document. The amounts used of each reactant are shown.  Either draw or describe a better alternative to this mechanism. (Note that the first step represents two steps combined and the proton loss is not even shown; fixing these is not the desired improvement.)  (Hints: The first step is correct, the second step is not; and the amount of the anhydride is in large excess to serve a purpose.)
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Draw a reasonable mechanism for the following reaction:

Chapter 19 Solutions

Organic Chemistry: Principles And Mechanisms

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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