Introduction to General, Organic and Biochemistry
Introduction to General, Organic and Biochemistry
11th Edition
ISBN: 9781285869759
Author: Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher: Cengage Learning
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Chapter 19, Problem 19.43P
Interpretation Introduction

Interpretation:

N, N-diethyl m-toluamide (DEET) is the active ingredient in several common insect repellents. The acid and amine need to be identified from which DEET is synthesized.

Introduction to General, Organic and Biochemistry, Chapter 19, Problem 19.43P , additional homework tip  1

Concept Introduction:

Amides are formed by a reaction with a carboxylic acid and an amine which are the functional groups. This results in the formation of amide bond, in which OH group of carboxylic acid reacts with one of the H in amine group and CO-NH bond is formed. This bond is known as an amide bond.

The mechanism for formation of an amide is as follows taking example of propanoic acid and ethylamine:

Introduction to General, Organic and Biochemistry, Chapter 19, Problem 19.43P , additional homework tip  2

The hydrolysis of amide so formed can give back the carboxylic acid and amine.

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Using the data in Appendix C, determine which of the following bases is strong enough to deprotonate acetonitrile (CH3CN), so that equilibrium favors the products: (a) NaH; (b) Na2CO3; (c) NaOH; (d) NaNH2; (e) NaHCO3.
Explain why CH3 CH2 CH2NH2 is a Brønsted base. Its water solutions are basic. All substances containing nitrogen atoms are Brønsted bases. This amine is a proton donor. This amine can ассеpt a proton from a proton donor.
Determine which of the following bases is strong enough to deprotonate acetonitrile (CH3CN), so that equilibrium favors the products:(a) NaH; (b) Na2CO3; (c) NaOH; (d) NaNH2; (e) NaHCO3.
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