Eventhough a carboxylic acid contains \(-\mathrm{C}\) - group, it does not form oxime with hydroxyl amine because (a) hydroxyl amine is less reactive to carboxylic acids. (b) in this case hydroxyl amine acts as a reducing agent, oxidized to \(\mathrm{HNO}_{2}\). (c) the \(\sum \mathrm{C}=\mathrm{O}\) group enters into resonance with lone pairs of \(-\mathrm{OH}\) group. (d) the -OH group of carboxylic acid reacts with \(\mathrm{NH}_{2} \mathrm{OH}\).

Short Answer

Expert verified
Based on the analysis of the given options, the reason why carboxylic acids do not form oximes with hydroxylamine is because the carbonyl group (\(\sum \mathrm{C}=\mathrm{O}\)) enters into resonance with the lone pairs of the hydroxyl group (\(-\mathrm{OH}\)). This resonance causes the carbonyl carbon to be less electrophilic, limiting the nucleophilic attack by the nitrogen atom of hydroxylamine (\(\mathrm{NH}_2\mathrm{OH}\)) and preventing the formation of an oxime. Option (c) is the correct answer.

Step by step solution

01

Understand the reaction to form oximes

When aldehydes or ketones react with hydroxylamine (\(\mathrm{NH}_2\mathrm{OH}\)), an oxime is formed. Typically, the reaction is driven by the nucleophilic attack on the carbonyl \(\sum \mathrm{C}=\mathrm{O}\) group by the nitrogen atom of hydroxylamine. The oxygen atom of the \(\sum \mathrm{C}=\mathrm{O}\) is then protonated and replaced with the nitrogen atom.
02

Examine the structure of carboxylic acid

A carboxylic acid has a structure \(\mathrm{R-COOH}\), which is an \(\mathrm{R-C}\) bond with a carbonyl group (\(\sum \mathrm{C}=\mathrm{O}\)) and a hydroxyl group (\(-\mathrm{OH}\)).
03

Analyze the given answers

(a) Although hydroxylamine can be less reactive to carboxylic acids, it is not the main reason why it does not form oximes with carboxylic acids. (b) In this case, hydroxylamine does not act as a reducing agent and is not oxidized to \(\mathrm{HNO}_2\) during the reaction. (c) Option (c) suggests that the carbonyl group \(\sum \mathrm{C}=\mathrm{O}\) enters into resonance with the lone pair of electrons of the hydroxyl group (\(-\mathrm{OH}\)). Due to resonance, the delocalization of electrons causes the carbonyl carbon to be less electrophilic, so the nucleophilic attack by the nitrogen atom of hydroxylamine (\(\mathrm{NH}_2\mathrm{OH}\)) is less likely to occur, thus not forming an oxime. (d) The -OH group of the carboxylic acid does not react with \(\mathrm{NH}_2\mathrm{OH}\) in this case.
04

Identify the correct answer

Based on the analysis, the correct answer is (c): the \(\sum \mathrm{C}=\mathrm{O}\) group enters into resonance with the lone pairs of the \(-\mathrm{OH}\) group. This resonance makes the carbonyl group less electrophilic and less reactive for nucleophilic attack by hydroxylamine, resulting in no oxime formation.

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Most popular questions from this chapter

Identify the true statements about methanoic acid. (a) It is formed by heating glycerol with oxalic acid to about \(373 \mathrm{~K}\). (b) It gives formyl chloride when treated with \(\mathrm{PCl}_{5^{*}}\) (c) It is a stronger acid than benzoic acid. (d) It gives carbon monoxide on heating with con. \(\mathrm{H}_{2} \mathrm{SO}_{4}\).

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