ORGANIC CHEMISTRY  W/CONNECT
ORGANIC CHEMISTRY W/CONNECT
10th Edition
ISBN: 9781307048513
Author: Carey
Publisher: MCG/CREATE
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Chapter 22, Problem 23P
Interpretation Introduction

Interpretation:

The structural formulas for all the amines of molecular formula C4H11N are to be written. An acceptable name is to be given for each formula and their classification is to be done as primary, secondary, or tertiary amine.

Concept introduction:

If the molecular formula of two compounds is same but their atoms are connected in different ways, they are known as constitutional or structural isomers.

In primary amines, the nitrogen atom is connected to two hydrogen atoms. In secondary amines, the nitrogen atom is connected to one hydrogen atom and tertiary amines have no hydrogen atom connected to the nitrogen atom.

Expert Solution & Answer
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Answer to Problem 23P

Solution:

The structural formulas for all the amines of molecular formula C4H11N along with their acceptable names and classification as primary, seconadry, or tertiary amine can be written as follows.

ORGANIC CHEMISTRY  W/CONNECT, Chapter 22, Problem 23P , additional homework tip  1

Explanation of Solution

The given molecular formula is C4H11N. The constitutional isomers of compound that has molecular formula C4H11N are shown below.

ORGANIC CHEMISTRY  W/CONNECT, Chapter 22, Problem 23P , additional homework tip  2

In each of the above isomer, the functional group is amine group. Therefore, the suffix used while naming the isomer is amine. On the basis of the number of hydrogen atoms attached to the nitrogen, the given isomers are classified as primary, secondary, and tertiary amine.

Conclusion

The structural formulas for all the seven isomeric amines possible for the molecular formula C4H11N are written and acceptable names are written for each of them. Their classification as primary, secondary, or tertiary amine is done on the basis of number of hydrogen atoms attached to the nitrogen atom in the amine.

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a.Primary amides tend to exist as dimers in the solid and liquid state. b.Dimethylacetamide, CH3CON(CH3)2 has a higher boiling point than acetamide. c.Nitrile is often classified as an acid derivative because it is hydrolyzed to a -COOH. d.Esters have lower boiling points than ketones of comparable molecular masses. Whice are correct?
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