ORGANIC CHEMISTRY-OWL V2 ACCESS
ORGANIC CHEMISTRY-OWL V2 ACCESS
8th Edition
ISBN: 9781305582422
Author: Brown
Publisher: CENGAGE L
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Chapter 21.5, Problem 21.7P

(a)

Interpretation Introduction

Interpretation: The products resulting from the vigorous oxidation of the given compound by H2CrO4 have to be predicted.

Concept Introduction:

Oxidation with H2CrO4at benzylic position:

The carbon atom attached to the benzene ring is known as benzylic carbon atom. The benzylic carbon that is attached with a benzylic hydrogen atom will be oxidized into carboxylic acid group on treatment with chromic acid (H2CrO4). In this process, the other groups attached to the benzylic carbon atom will be removed.

General scheme:

ORGANIC CHEMISTRY-OWL V2 ACCESS, Chapter 21.5, Problem 21.7P , additional homework tip  1

(b)

Interpretation Introduction

Interpretation: The products resulting from the vigorous oxidation of the given compound by H2CrO4 have to be predicted.

Concept Introduction:

Oxidation with H2CrO4at benzylic position:

The carbon atom attached to the benzene ring is known as benzylic carbon atom. The benzylic carbon that is attached with a benzylic hydrogen atom will be oxidized into carboxylic acid group on treatment with chromic acid (H2CrO4). In this process, the other groups attached to the benzylic carbon atom will be removed as CO2 .

General scheme:

ORGANIC CHEMISTRY-OWL V2 ACCESS, Chapter 21.5, Problem 21.7P , additional homework tip  2

In this oxidation, halogen and nitro substituents on the benzene ring are unaffected as shown in the following example:

Example:

ORGANIC CHEMISTRY-OWL V2 ACCESS, Chapter 21.5, Problem 21.7P , additional homework tip  3

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Chapter 21 Solutions

ORGANIC CHEMISTRY-OWL V2 ACCESS

Ch. 21 - Name the following compounds and ions.Ch. 21 - Prob. 21.9PCh. 21 - Draw a structural formula for each compound. (a)...Ch. 21 - Molecules of 6,6-dinitrobiphenyl-2,2-dicarboxylic...Ch. 21 - Following each name is the number of Kekul...Ch. 21 - Prob. 21.13PCh. 21 - Prob. 21.14PCh. 21 - Prob. 21.15PCh. 21 - Which of the molecules and ions given in Problem...Ch. 21 - Prob. 21.17PCh. 21 - Naphthalene and azulene are constitutional isomers...Ch. 21 - Prob. 21.19PCh. 21 - Prob. 21.20PCh. 21 - Following are IR and 1H-NMR spectra of compound D....Ch. 21 - Compound E (C8H10O2) is a neutral solid. Its mass...Ch. 21 - Following are 1H-NMR and 13C-NMR spectral data for...Ch. 21 - Following are 1H-NMR and 13C-NMR spectral data for...Ch. 21 - Compound H (C8H6O3) gives a precipitate when...Ch. 21 - Compound I (C11H14O2) is insoluble in water,...Ch. 21 - Propose a structural formula for compound J...Ch. 21 - Propose a structural formula for the analgesic...Ch. 21 - Prob. 21.29PCh. 21 - Prob. 21.30PCh. 21 - Given here are 1H-NMR and 13C-NMR spectral data...Ch. 21 - Prob. 21.32PCh. 21 - Prob. 21.33PCh. 21 - Prob. 21.34PCh. 21 - Arrange the molecules and ions in each set in...Ch. 21 - Prob. 21.36PCh. 21 - Prob. 21.37PCh. 21 - From each pair, select the stronger base.Ch. 21 - Prob. 21.39PCh. 21 - Prob. 21.40PCh. 21 - Prob. 21.41PCh. 21 - Prob. 21.42PCh. 21 - Following is an equation for iodination of...Ch. 21 - Prob. 21.44PCh. 21 - Prob. 21.45PCh. 21 - Prob. 21.46PCh. 21 - When warmed in dilute sulfuric acid,...Ch. 21 - In the chemical synthesis of DNA and RNA, hydroxyl...Ch. 21 - Prob. 21.49PCh. 21 - Write the products of the following sequences of...Ch. 21 - Prob. 21.51PCh. 21 - Show how to convert 1-phenylpropane into the...Ch. 21 - Prob. 21.53PCh. 21 - Cromolyn sodium, developed in the 1960s, has been...Ch. 21 - Prob. 21.55PCh. 21 - Prob. 21.56PCh. 21 - Prob. 21.57PCh. 21 - Prob. 21.58PCh. 21 - Prob. 21.59PCh. 21 - Prob. 21.60PCh. 21 - Prob. 21.61PCh. 21 - Prob. 21.62PCh. 21 - Prob. 21.63PCh. 21 - Following is a synthesis for toremifene, a...
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