Organic Chemistry (6th Edition)
Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 23.6, Problem 15P
Interpretation Introduction

(a)

Interpretation: The reason corresponding to the fact that phentermine cannot be made by reductive amination reaction is to be stated.

Concept introduction: The conversion of aldehydes and ketones into amines is known as reductive amination. The first step is the formation of imines using aldehydes or ketones and amines. The second step involves the reduction of imine to form amine. The best reagent for this reaction is sodiumcyanoborohydride.

Interpretation Introduction

(b)

Interpretation: The systematic name for phentermine, is to be predicted.

Concept introduction: IUPAC nomenclature is a systematic way of naming the organic compounds. The basic principles of IUPAC naming for hydrocarbon are:

1. The hydrocarbon is named after the carbon chain containing higher number of carbon atoms.

2. The parent alkane containing amino group is named as alkane with suffix amine.

3. When the nitrogen atom of amine is substituted with alkyl groups, then the amine is named with prefix N before the alkyl groups.

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(a) Explain why phentermine [PhCH2C(CH3)2NH2] can’t be made by a reductive amination reaction.(b) Give a systematic name for phentermine, one of the components of the banned diet drug fen–phen.
Fenfluramine and phentermine are two components of fen–phen, an appetite suppressant withdrawn from the market in 1997 after it was shown to damage the heart valves in some patients. What products are formed when fenfluramine and phentermine are each treated with acetic acid (CH3CO2H)?
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.
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