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Carboxylic acids contain carbonyl group but do not show the nucleophilic addition reaction like aldehydes or ketones. Why?

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प्रश्न

Carboxylic acids contain carbonyl group but do not show the nucleophilic addition reaction like aldehydes or ketones. Why?

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उत्तर

It is due to resonance as shown below. The partial positive charge on the carbonyl carbon atom is reduced

Similarly, a carbonyl group of aldehydes and ketones may be regarded as the resonance hybrid of the following structures.

The carbonyl carbon of carboxylic group is less electrophilic than carbonyl carbon in aldehydes and ketones and hence nucleophilic addition reactions of aldehydes and ketones do not takes place with carboxylic acids.

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अध्याय 12: Aldehydes, Ketones and Carboxylic Acids - Multiple Choice Questions (Type - I) [पृष्ठ १७३]

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एनसीईआरटी एक्झांप्लर Chemistry Exemplar [English] Class 12
अध्याय 12 Aldehydes, Ketones and Carboxylic Acids
Multiple Choice Questions (Type - I) | Q 32 | पृष्ठ १७३

संबंधित प्रश्न

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benzaldehyde from benzene


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1) `LiAlH_4"/"H_3O^+`

2) `PCl_3 , "heat"`

3) `P_2O_5, "heat"`


Write the structure of Phenylmethanamine.


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\[\ce{Carbonyl compound + MeOH <=>[HCl] acetal}\]

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The following questions are case-based questions. Read the passage carefully and answer the questions that follow:

The carbon-oxygen double bond is polarised in aldehydes and ketones due to higher electronegativity of oxygen relative to carbon. Therefore, they undergo nucleophilic addition reactions with a number of nucleophiles such as HCN, NaHSO3, alcohols, ammonia derivatives and Grignard reagents. Aldehydes are easily oxidised by mild oxidising agents as compared to ketones. The carbonyl group of carboxylic acid does not give reactions of aldehydes and ketones. Carboxylic acids are considerably more acidic than alcohols and most of simple phenols.

Answer the following:

(a) Write the name of the product when an aldehyde reacts with excess alcohol in the presence of dry HCl. (1)

(b) Why carboxylic acid is a stronger acid than phenol? (1)

(c) (i) Arrange the following compounds in increasing order of their reactivity towards CH3MgBr: (1)

CH3CHO, \[\begin{array}{cc}
\ce{(CH3)3C-C-CH3}\\
\phantom{....}||\\
\phantom{....}\ce{O}
\end{array}\],  \[\begin{array}{cc}
\ce{CH3-C-CH3}\\
||\\
\ce{O}
\end{array}\]

(ii) Write a chemical test to distinguish between propanal and propanone. (1)

OR

(c) Write the main product in the following: (2)

(i)
(ii)

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Draw structure of the following derivative.

The ethylene ketal of hexan-3-one


Give an example of the reaction in the following case.

Imine


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