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Chapter 22: Problem 29

Draw the structural isomers of the alkane \(\mathrm{C}_{6} \mathrm{H}_{14} .\)

Short Answer

Expert verified
Answer: There are five structural isomers of C6H14: 1. Hexane 2. 2-methylpentane 3. 3-methylpentane 4. 2,2-dimethylbutane 5. 2,3-dimethylbutane.

Step by step solution

01

Identify the longest carbon chain

The longest carbon chain of C6H14 contains six carbon atoms. We will consider this as the parent chain and draw the first isomer called hexane.
02

Draw hexane

Hexane has six consecutive carbon atoms connected by single bonds and each carbon atom surrounded by hydrogen atoms. The structure can be represented as: \(\mathrm{CH}_{3} - \mathrm{CH}_{2} - \mathrm{CH}_{2} - \mathrm{CH}_{2} - \mathrm{CH}_{2} - \mathrm{CH}_{3}\)
03

Draw five-carbon chain isomers

Next, we will consider five-carbon chains with a one-carbon branch. There are two possible isomers: 2-methylpentane and 3-methylpentane. 2-methylpentane: \(\mathrm{CH}_{3} - \mathrm{CH} - \mathrm{CH}_{2} - \mathrm{CH}_{2} - \mathrm{CH}_{3}\) | \(\mathrm{CH}_{3}\) 3-methylpentane: \(\mathrm{CH}_{3} - \mathrm{CH}_{2} - \mathrm{CH} - \mathrm{CH}_{2} - \mathrm{CH}_{3}\) | \(\mathrm{CH}_{3}\)
04

Draw four-carbon chain isomers

Next, we will consider four-carbon chains with two or more branches. There are three possible isomers: 2,2-dimethylbutane, 2,3-dimethylbutane, and 3,3-dimethylbutane. 2,2-dimethylbutane: \(\mathrm{CH}_{3} - \mathrm{C} - \mathrm{CH}_{2} - \mathrm{CH}_{3}\) | \(\mathrm{CH}_{3}\) | \(\mathrm{CH}_{3}\) 2,3-dimethylbutane: \(\mathrm{CH}_{3} - \mathrm{CH} - \mathrm{CH} - \mathrm{CH}_{3}\) | | \(\mathrm{CH}_{3}\) \(\mathrm{CH}_{3}\) 3,3-dimethylbutane (not a valid isomer, since it is isomorphic to 2,2-dimethylbutane)
05

Identify all isomers of C6H14

The total number of structural isomers of \(\mathrm{C}_{6} \mathrm{H}_{14}\) is five. They are: 1. Hexane 2. 2-methylpentane 3. 3-methylpentane 4. 2,2-dimethylbutane 5. 2,3-dimethylbutane

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