Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
Question
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Chapter 20.SE, Problem 47AP
Interpretation Introduction

a) LiAlH4, then H3O+

Interpretation:

The product produced when p-methylbenzoic acid is treated with LiAlH4 and then with H3O+ is to be predicted.

Concept introduction:

Carboxylic acids get reduced to primary alcohols when treated with LiAlH4.

To predict:

The product produced when p-methylbenzoic acid is treated with LiAlH4 and then with H3O+.

Interpretation Introduction

b) N-Bromosuccinimide in CCl4

Interpretation:

The product produced when p-methylbenzoic acid is treated with N-bromosuccinimide in CCl4 is to be predicted.

Concept introduction:

N-bromosuccinimide in CCl4 is used for introducing a Br in the benzyl carbon.

To predict:

The product produced when p-methylbenzoic acid is treated with N-bromosuccinimide in CCl4.

Interpretation Introduction

c) CH3MgBr in ether, then H3O+

Interpretation:

The product produced when p-methylbenzoic acid is treated with CH3MgBr and then with H3O+ is to be predicted.

Concept introduction:

Grignard reagents will react with the carboxyl hydrogen to yield alkanes.

To predict:

The product produced when p-methylbenzoic acid is treated with CH3MgBr and then with H3O+.

Interpretation Introduction

d) KMnO4, H3O+

Interpretation:

The product produced when p-methylbenzoic acid is treated with KMnO4 in the presence of H3O+ is to be predicted.

Concept introduction:

When treated with KMnO4 in the presence of H3O+, the side chain in aromatic compounds is oxidized to carboxyl group.

To predict:

The product produced when p-methylbenzoic acid is treated with KMnO4 in the presence of H3O+.

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Chapter 20 Solutions

Organic Chemistry

Ch. 20.6 - Prob. 11PCh. 20.6 - How might you carry out the following...Ch. 20.7 - Prob. 13PCh. 20.7 - Prob. 14PCh. 20.8 - Cyclopentanecarboxylic acid and...Ch. 20.8 - Prob. 16PCh. 20.SE - Prob. 17VCCh. 20.SE - Prob. 18VCCh. 20.SE - The following carboxylic acid can’t be prepared...Ch. 20.SE - Electrostatic potential maps of anisole and...Ch. 20.SE - Predict the product(s) and provide the mechanism...Ch. 20.SE - Predict the product(s) and provide the mechanism...Ch. 20.SE - Prob. 23MPCh. 20.SE - Predict the product(s) and provide the complete...Ch. 20.SE - Acid-catalyzed hydrolysis of a nitrile to give a...Ch. 20.SE - Prob. 26MPCh. 20.SE - Naturally occurring compounds called cyanogenic...Ch. 20.SE - 2-Bromo-6, 6-dimethylcyclohexanone gives 2,...Ch. 20.SE - Naturally occurring compounds called terpenoids,...Ch. 20.SE - In the Ritter reaction, an alkene reacts with a...Ch. 20.SE - Give IUPAC names for the following compounds:Ch. 20.SE - Prob. 32APCh. 20.SE - Prob. 33APCh. 20.SE - Prob. 34APCh. 20.SE - Prob. 35APCh. 20.SE - Prob. 36APCh. 20.SE - Prob. 37APCh. 20.SE - Prob. 38APCh. 20.SE - Calculate the Ka's for the following acids: (a)...Ch. 20.SE - Thioglycolic acid, HSCH2CO2H, a substance used in...Ch. 20.SE - Prob. 41APCh. 20.SE - Prob. 42APCh. 20.SE - How could you convert butanoic acid into the...Ch. 20.SE - How could you convert each of the following...Ch. 20.SE - How could you convert butanenitrile into the...Ch. 20.SE - How would you prepare the following compounds from...Ch. 20.SE - Prob. 47APCh. 20.SE - Using 13CO2 as your only source of labeled carbon,...Ch. 20.SE - Prob. 49APCh. 20.SE - Which method-Grignard carboxylation or nitrile...Ch. 20.SE - Prob. 51APCh. 20.SE - Prob. 52APCh. 20.SE - Propose a structure for a compound C6H12O2 that...Ch. 20.SE - Prob. 54APCh. 20.SE - How would you use NMR (either 13C or 1H) to...Ch. 20.SE - Prob. 56APCh. 20.SE - A chemist in need of 2,2-dimethylpentanoic acid...Ch. 20.SE - Prob. 58APCh. 20.SE - Prob. 59APCh. 20.SE - Prob. 60APCh. 20.SE - Prob. 61APCh. 20.SE - Prob. 62APCh. 20.SE - Prob. 63APCh. 20.SE - The following pKa values have been measured....Ch. 20.SE - Identify the missing reagents a-f in the following...Ch. 20.SE - Propose a structure for a compound, C4H7N, that...Ch. 20.SE - Prob. 67APCh. 20.SE - The 1H and 13C NMR spectra below belong to a...Ch. 20.SE - Propose structures for carboxylic acids that show...Ch. 20.SE - Carboxylic acids having a second carbonyl group...
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