MCQMediumJEE 2025Carboxylic Acids

JEE Chemistry 2025 Question with Solution

Reaction scheme showing compound A converting to B using NaOH followed by H3O+, then B converting to C using EtOH and H2SO4 under heat.

A shows positive Lassaigne's test for N and its molar mass is 121121

B gives effervescence with aqueous NaHCO3\text{NaHCO}_3

C gives fruity smell.

Identify A, B, and C from the following.

  • A

    A = CONH2\text{CONH}_2, B = CO2H\text{CO}_2\text{H}, C = CO2Et\text{CO}_2\text{Et}

  • B

    Option text could not be extracted from the provided HTML.

  • C

    Option text could not be extracted from the provided HTML.

  • D

    Option text could not be extracted from the provided HTML.

Answer

Correct answer:A

Step-by-step solution

Standard Method

Given: Compound A shows a positive Lassaigne's test for NN and has molar mass 121121. Compound B gives effervescence with aqueous NaHCO3\text{NaHCO}_3. Compound C gives fruity smell. The scheme shows A converting to B with NaOH\text{NaOH} followed by H3O+\text{H}_3\text{O}^+, and B converting to C with EtOH\text{EtOH} and H2SO4,Δ\text{H}_2\text{SO}_4, \Delta.

Find: Identify A, B, and C.

A positive Lassaigne's test for nitrogen shows that A contains nitrogen. From the solution working, the molar mass 121121 matches benzamide.

Treatment with base followed by acidic workup converts an amide into the corresponding carboxylic acid. Therefore,

benzamideNaOH,H3O+benzoic acid\text{benzamide} \xrightarrow{\text{NaOH},\, \text{H}_3\text{O}^+} \text{benzoic acid}

So B is benzoic acid.

Effervescence with aqueous NaHCO3\text{NaHCO}_3 is characteristic of a carboxylic acid because CO2\text{CO}_2 is evolved.

The next step uses EtOH\text{EtOH} and H2SO4\text{H}_2\text{SO}_4 with heating, which is esterification:

benzoic acid+ethanolethyl benzoate+water\text{benzoic acid} + \text{ethanol} \rightarrow \text{ethyl benzoate} + \text{water}

Esters give a fruity smell, so C is ethyl benzoate.

Therefore, A = benzamide, B = benzoic acid, C = ethyl benzoate. The correct option is A.

The solution indicates a discrepancy in the listed options: only the correct option content could be inferred from the solution, while the full option list was not available.

Functional Group Identification

Given:

  • A gives positive Lassaigne's test for NN
  • Molar mass of A is 121121
  • B gives effervescence with aqueous NaHCO3\text{NaHCO}_3
  • C gives fruity smell

Find: The identities of A, B, and C.

  1. For A, the positive Lassaigne's test confirms the presence of nitrogen.
  2. The solution text identifies the nitrogen-containing compound of molar mass 121121 as benzamide with formula C7H7NO\text{C}_7\text{H}_7\text{NO}.
  3. Hydrolysis of an amide with NaOH\text{NaOH} followed by acidification gives the corresponding carboxylic acid. Hence B is benzoic acid.
  4. A compound that reacts with aqueous NaHCO3\text{NaHCO}_3 with effervescence must be a carboxylic acid, supporting that B is benzoic acid.
  5. Reaction of a carboxylic acid with ethanol in presence of sulfuric acid and heat gives an ester. Thus C is ethyl benzoate.
  6. Fruity smell is also a characteristic property of esters, confirming C.

Therefore, the identified set is benzamide, benzoic acid, ethyl benzoate, so the correct option is A.

Common mistakes

  • Assuming that a positive Lassaigne's test for nitrogen identifies only any amine is incorrect. The test only confirms the presence of nitrogen; the molar mass and reaction sequence must also be used. Here, the correct identification is benzamide, not a low-molar-mass amine.

  • Missing that effervescence with aqueous NaHCO3\text{NaHCO}_3 is a specific test for carboxylic acids leads to wrong identification of B. Phenols and alcohols do not show this reaction. Use the CO2\text{CO}_2 evolution clue to identify B as benzoic acid.

  • Ignoring that fruity smell is characteristic of esters can lead to choosing an alcohol or acid for C. Since B reacts with EtOH\text{EtOH} in acidic medium on heating, the product must be an ester, namely ethyl benzoate.

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