Organic Chemistry (8th Edition)

Published by Pearson
ISBN 10: 0321768418
ISBN 13: 978-0-32176-841-4

Chapter 2 - Structure and Properties of Organic Molecules - Study Problems - Page 85: 2-38

Answer

The molecules have dramatically different boiling points because of hydrogen bonding. Explained in detail below.

Work Step by Step

Structure of diethyl ether is $CH_3-CH_2-O-CH_2-CH_3$. Structure of butan-1-ol is $CH_3-CH_2-CH_2-CH_2-OH$. Both these compounds have one oxygen, therefore they can both form hydrogen bonds with water. So, their solubilities are similar. But the molecules of butan-1-ol can also hydrogen bond with each other, but the molecules of diethyl ether cannot. So, more energy is needed to vaporise butan-1-ol. So, boiling point of butan-1-ol is much higher than that of diethl ether.
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