MCQEasyJEE 2025Alcohols

JEE Chemistry 2025 Question with Solution

Which among the following compounds give yellow solid when reacted with NaOI/NaOH?

Five organic compounds labeled A to E: secondary alcohol, primary alcohol, methyl ketone, carboxylic acid, and aldehyde structures shown.

Choose the correct answer from the options given below:

  • A

    (B), (C) and (E) Only

  • B

    (A) and (C) Only

  • C

    (C) and (D) Only

  • D

    (A), (C) and (D) Only

Answer

Correct answer:B

Step-by-step solution

Standard Method

Given: We must identify which compounds give a yellow solid with NaOI/NaOH.

Find: Which labeled compounds undergo the iodoform reaction and hence form yellow CHI3\mathrm{CHI_3}.

This is the haloform reaction. A yellow precipitate is formed by compounds containing the methyl ketone group CH3COR\mathrm{CH_3COR}, or by alcohols of the type CH3CH(OH)R\mathrm{CH_3CH(OH)R} because they are oxidized to methyl ketones under these conditions.

From the given structures:

  • (A) is CH3CH(OH)C2H5\mathrm{CH_3-CH(OH)-C_2H_5}, a secondary alcohol of type CH3CH(OH)R\mathrm{CH_3CH(OH)R}, so it gives the iodoform test.
  • (B) is CH3CH2CH2OH\mathrm{CH_3-CH_2-CH_2-OH}, a primary alcohol, so it does not give the test.
  • (C) is CH3COC2H5\mathrm{CH_3COC_2H_5}, a methyl ketone, so it gives the test.
  • (D) is CH3COOH\mathrm{CH_3COOH}, a carboxylic acid, so it does not give the test.
  • (E) is CH3CH2CHO\mathrm{CH_3CH_2CHO}, an aldehyde other than ethanal, so it does not give the test.

Therefore, the compounds that give yellow solid are (A) and (C) only. Hence, the correct option is B.

Using the iodoform criterion

Given: NaOI/NaOH gives a yellow solid in the iodoform test.

Find: Which of (A) to (E) satisfy the structural requirement.

The required structural conditions are:

  1. A methyl ketone: CH3COR\mathrm{CH_3COR}
  2. Or a secondary alcohol oxidizable to a methyl ketone: CH3CH(OH)R\mathrm{CH_3CH(OH)R}

Checking each compound one by one:

  • (A) fits CH3CH(OH)R\mathrm{CH_3CH(OH)R} with R=C2H5\mathrm{R=C_2H_5}.
  • (B) is CH3CH2CH2OH\mathrm{CH_3CH_2CH_2OH} and does not fit the required pattern.
  • (C) directly fits CH3COR\mathrm{CH_3COR}.
  • (D) is a carboxylic acid, not a methyl ketone.
  • (E) is propanal, not ethanal, so it does not respond positively.

Thus only (A) and (C) form the yellow precipitate of iodoform. The correct option is B.

The second provided approach contains inconsistent structural descriptions, but the conclusion supported by the valid structural analysis is B.

Common mistakes

  • Assuming every alcohol gives the yellow precipitate is incorrect. Only alcohols of type CH3CH(OH)R\mathrm{CH_3CH(OH)R} are oxidized to methyl ketones. Check the carbon bearing OH\mathrm{OH} before concluding.

  • Treating any carbonyl compound as positive for the test is wrong. The compound must be a methyl ketone CH3COR\mathrm{CH_3COR}, not just any aldehyde or carboxylic acid.

  • Marking propanal (E) as positive is a common error. In the aldehydes, essentially only ethanal gives the iodoform reaction; CH3CH2CHO\mathrm{CH_3CH_2CHO} does not. Use the specific structural criterion instead of guessing from functional group name alone.

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