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Chapter 12: Problem 6

In which of the following compounds do you think that intramolecular hydrogen bonding is an important factor: $(\mathrm{a}) \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3} ;(\mathrm{b}) \mathrm{HOOCCH}_{2} \mathrm{CH}_{2}$ $\mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{COOH} ;(\mathrm{c}) \mathrm{CH}_{3} \mathrm{COOH} ;$ (d) ortho-phthalic acid? Explain.

Short Answer

Expert verified
Intramolecular hydrogen bonding is an important factor in compound b (\(\mathrm{HOOCCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{COOH\)), compound c (\(\mathrm{CH}_{3} \mathrm{COOH}\)), and in ortho-phthalic acid. It is not important in compound a (\(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\)) as it lacks the required highly electronegative atom

Step by step solution

01

Identify Hydrogen Bonding Capability

Intramolecular hydrogen bonding requires a hydrogen atom to be bonded to a highly electronegative atom (like N, O, F) and the presence of another electronegative atom within the same molecule. The structures need to be examined for these criteria.
02

Analyze Compound (a)

For compound a (\(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\)), there are no highly electronegative atoms present (like N, O, F), and thus, it is not capable of hydrogen bonding.
03

Analyze Compound (b)

For compound b (\(\mathrm{HOOCCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{COOH\)), there exists a hydrogen atom bonded to an oxygen atom (in -COOH) and another oxygen atom within the same molecule. Therefore, intramolecular hydrogen bonding is likely to occur here.
04

Analyze Compound (c)

For compound c (\(\mathrm{CH}_{3} \mathrm{COOH}\)), the hydrogen in the -COOH group can potentially form a hydrogen bond with the oxygen in the -COOH group present on the same molecule. Therefore, intramolecular hydrogen bonding is also possible.
05

Analyze Compound (d)

Ortho-phthalic acid has two -COOH groups very close to each other within the same molecule. Thus, a hydrogen from one -COOH can form a bond with the oxygen of the neighbouring -COOH group. Therefore, intramolecular hydrogen bonding is possible here too.

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