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Chapter 4: Problem 133

Directions: This section contains multiple choice questions. Each question has 4 choices (a), (b), (c) and (d), out of which ONLY ONE is correct. Which of the following isomeric alcohols has the highest solubility in water? (a)n-butyl alcohol (b) sec-butyl alcohol (c) isobutyl alcohol (d) tert-butyl alcohol

Short Answer

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a. n-butyl alcohol b. sec-butyl alcohol c. isobutyl alcohol d. tert-butyl alcohol Answer: d. tert-butyl alcohol

Step by step solution

01

Understanding the structures of the given isomeric alcohols

The first step is to understand the structures of the given alcohols: 1. n-butyl alcohol (CH3CH2CH2CH2OH) 2. sec-butyl alcohol (CH3CH2CHOHCH3) 3. isobutyl alcohol (CH3CH2CH(CH3)OH) 4. tert-butyl alcohol (CH3C(CH3)2OH) Notice that all of them have a single OH group as a hydrogen bond donor.
02

Comparing the structures of the given alcohols

Now we will compare the structures of the alcohols. The hydrogen bonding capacity of each alcohol is identical, as they all have a single OH group. However, their solubility in water will be influenced by the size and branching of their alkyl chains. Alcohols with smaller and more branched alkyl chains will generally have a higher solubility in water due to the decrease in the hydrophobic (water-repelling) interactions with their alkyl groups.
03

Determining the alcohol with the highest solubility in water

Comparing the given alcohols, we can see that tert-butyl alcohol (d) has the shortest and most branched alkyl group and is likely to form the strongest hydrogen bonds with water molecules. Therefore, it has the highest solubility in water. So the correct answer is (d) tert-butyl alcohol.

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