ORGANIC CHEMISTRY-ETEXT REG ACCESS
ORGANIC CHEMISTRY-ETEXT REG ACCESS
12th Edition
ISBN: 9781119308362
Author: Solomons
Publisher: WILEY
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Chapter 20, Problem 1PP
Interpretation Introduction

Interpretation:

The procedure for separation of hexylamine from cyclohexane using dilute HCl, aqueous NaOH and diethyl ether is to be explained..

Concept Introduction:

Amines are organic derivatives of ammonia, in which hydrogen atoms are replaced by some organic compounds.

On the basis of hydrogen atoms being replaced from ammonia by the organic groups, amines are of three types: primary amines (RNH2), secondary amines (R2NH) and tertiary amines (R3N). Amines are soluble in dilute acids.

Expert Solution & Answer
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Answer to Problem 1PP

Solution: Hexylamine is soluble in dilute acids but cyclohexane is not.

Explanation of Solution

Given information: A solution of cyclohexane and hexylamine is to be separated by dilute acid, aqueous NaOH and diethyl ether.

Amines with larger number of carbon atoms are insoluble in water but they are soluble in dilute acids. Thus, by dissolving amines in acids, they can be separated easily. Amines carry a lone pair, which forms a bond with the hydrogen atoms of acids while, cyclohexane being non-polar does not interact with acids. The interaction of amines with dilute acid is shown below:

ORGANIC CHEMISTRY-ETEXT REG ACCESS     , Chapter 20, Problem 1PP

The separated amines can be extracted from acid by dissolving in aqueous acid solution and then recovered by making the aqueous solution basic and extracting the amine in etheror CH2Cl2.

Conclusion

Hexylamine can be separated from cyclohexane by dissolving the amine derivative in dilute acid solution.

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Chapter 20 Solutions

ORGANIC CHEMISTRY-ETEXT REG ACCESS

Ch. 20 - Practice Problem 20.11 In the preceding examples...Ch. 20 - Prob. 12PPCh. 20 - Prob. 13PPCh. 20 - Practice Problem 20.14 Outline a synthesis of...Ch. 20 - Prob. 15PPCh. 20 - Prob. 16PPCh. 20 - Prob. 17PPCh. 20 - Prob. 18PPCh. 20 - Prob. 19PCh. 20 - 20.20 Give common or systematic names for each of...Ch. 20 - Which is the most basic nitrogen in each compound?...Ch. 20 - Prob. 22PCh. 20 - Prob. 23PCh. 20 - Show how you might synthesize each of the...Ch. 20 - Prob. 25PCh. 20 - 20.26 Provide the major organic product from each...Ch. 20 - Prob. 27PCh. 20 - 20.28 What products would you expect to be formed...Ch. 20 - Prob. 29PCh. 20 - Prob. 30PCh. 20 - Prob. 31PCh. 20 - Write equations for simple chemical rests or state...Ch. 20 - Prob. 33PCh. 20 - Explain the following, including mention of key...Ch. 20 - 20.35 Provide a detailed mechanism for each of the...Ch. 20 - Prob. 36PCh. 20 - Prob. 37PCh. 20 - Prob. 38PCh. 20 - Prob. 39PCh. 20 - 20.40 Give structures for compounds R-W: Ch. 20 - Prob. 41PCh. 20 - Prob. 42PCh. 20 - Diethylpropion (shown here) is a compound used in...Ch. 20 - Prob. 44PCh. 20 - 20.45 Compound W is soluble in dilute aqueous HCI...Ch. 20 - 20.46 Propose structures for compounds X, Y, and...Ch. 20 - Compound A(C10H15N) is soluble in dilute HCI. The...Ch. 20 - Prob. 48PCh. 20 - Prob. 49PCh. 20 - For each of the following, identify the product...Ch. 20 - 20.51 Develop a synthesis for the following...Ch. 20 - 20.52 When phenyl isochiocyanatc, , is reduced...Ch. 20 - Prob. 53PCh. 20 - 20.54 Propose a mechanism that can explain the...Ch. 20 - When acetone is treated with anhydrous ammonia in...Ch. 20 - Prob. 56P
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