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JEE Advanced 2019 Paper 1 · Chemistry · Carbonyl Compounds, Carboxylic Acids and Amines · medium

Propanal is treated with dilute aqueous NaOH at room temperature and the product is then heated to give X (aldol condensation).

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Propanal is treated with dilute aqueous NaOH\mathrm{NaOH} at room temperature and the product is then heated to give X\mathbf{X} (aldol condensation). The correct statement(s) is(are)
  1. A. X\mathbf{X} has the molecular formula C6H10O\mathrm{C_6H_{10}O}.
  2. B. X\mathbf{X} exhibits geometrical isomerism.
  3. C. Reductive ozonolysis of X\mathbf{X} gives propanal and ethanal.
  4. D. X\mathbf{X} gives a positive iodoform test.
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Answer: A, B

Two propanal molecules combine: the enolate of one (nucleophilic carbon C-2) attacks the carbonyl carbon of the other to give 3-hydroxy-2-methylpentanal; heating eliminates water to the conjugated enal X=CH3CH2CH=C(CH3)CHO\mathbf{X}=\mathrm{CH_3CH_2CH{=}C(CH_3)CHO}, 2-methylpent-2-enal. Formula: 2 C3H6O−H2O=C6H10O2\,\mathrm{C_3H_6O}-\mathrm{H_2O}=\mathrm{C_6H_{10}O}; (A) is true. Each alkene carbon bears two different substituents (C2: methyl and CHO; C3: ethyl and H), so E/Z isomerism exists; (B) is true. Cleaving the double bond gives CH3CH2CHO\mathrm{CH_3CH_2CHO} (propanal) and CH3COCHO\mathrm{CH_3COCHO} (2-oxopropanal), not ethanal, so (C) is false. There is no CH3CO−\mathrm{CH_3CO{-}} group or CH3CH(OH)−\mathrm{CH_3CH(OH){-}} unit, so the iodoform test is negative and (D) is false.
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