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JEE Advanced 2022 Paper 1 · Chemistry · Qualitative and Practical Chemistry · medium

Match the carbonyl compounds in List-I with the correct set of observations in List-II. Ethanal | 1. Reduces Tollens' reagent; no yellow precipitate…

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Match the carbonyl compounds in List-I with the correct set of observations in List-II.

| List-I | List-II |
|---|---|
| P. Ethanal | 1. Reduces Tollens' reagent; no yellow precipitate with I2/NaOH\mathrm{I_2/NaOH} |
| Q. Butan-2-one | 2. Yellow precipitate with I2/NaOH\mathrm{I_2/NaOH}; does not reduce Tollens' reagent |
| R. 2-Hydroxyacetophenone | 3. Reduces Tollens' reagent and also gives a yellow precipitate with I2/NaOH\mathrm{I_2/NaOH} |
| S. Benzaldehyde | 4. Violet colour with neutral FeCl3\mathrm{FeCl_3} and a yellow precipitate with I2/NaOH\mathrm{I_2/NaOH} |
| | 5. Violet colour with neutral FeCl3\mathrm{FeCl_3}; no yellow precipitate with I2/NaOH\mathrm{I_2/NaOH} |
  1. A. P→3, Q→2, R→4, S→1
  2. B. P→1, Q→2, R→4, S→3
  3. C. P→3, Q→2, R→5, S→1
  4. D. P→3, Q→4, R→2, S→1
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Answer: (A) P→3, Q→2, R→4, S→1

P: ethanal is an aldehyde (reduces Tollens' reagent) and has the CH3CO−\mathrm{CH_3CO{-}} group attached to H, so it gives the iodoform test: 3. Q: butan-2-one is a methyl ketone, positive iodoform, but a ketone does not reduce Tollens' reagent: 2. R: 2-hydroxyacetophenone has a phenolic OH (violet colour with neutral FeCl3\mathrm{FeCl_3}) and the COCH3\mathrm{COCH_3} methyl-ketone group (iodoform positive); it is not an aldehyde, so Tollens' is negative: 4. S: benzaldehyde reduces Tollens' reagent but has no CH3CO\mathrm{CH_3CO} or CH3CH(OH)\mathrm{CH_3CH(OH)} unit, so no iodoform: 1. Entry 5 describes a phenol without a methyl ketone and matches none. Correct code: P→3, Q→2, R→4, S→1.
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