Two compounds A and B with same molecular formula (\(\mathrm{C_3H_6O}\)) undergo Grignard's reaction with methylmagnesium bromide to give products C and D. Products C and D show following chemical tests.
Test C D Ceric ammonium nitrate Test Positive Positive Lucas Test Turbidity obtained after five minutes Turbidity obtained immediately Iodoform Test Positive Negative
C and D respectively are :
| Test | C | D |
| Ceric ammonium nitrate Test | Positive | Positive |
| Lucas Test | Turbidity obtained after five minutes | Turbidity obtained immediately |
| Iodoform Test | Positive | Negative |
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The Correct Option is D
Solution and Explanation
Propanal + \(\mathrm{CH_3MgBr}\), then hydrolysis, gives \(\mathrm{CH_3CH_2CH(OH)CH_3}\) (butan-2-ol), a secondary alcohol.
Propanone + \(\mathrm{CH_3MgBr}\), then hydrolysis, gives \(\mathrm{(CH_3)_3C-OH}\) (2-methylpropan-2-ol), a tertiary alcohol.
Lucas test: tertiary alcohol gives turbidity immediately; secondary alcohol gives turbidity after about five minutes. So D is the tertiary alcohol and C is the secondary alcohol.
Iodoform test: butan-2-ol has the \(\mathrm{CH_3CH(OH)-}\) unit, so it is positive (C); tert-butyl alcohol has no such unit, so it is negative (D). Both are alcohols, so both give a positive ceric ammonium nitrate test.
Hence C = butan-2-ol, D = 2-methylpropan-2-ol, which is option (4).
Answer: (4) C = \(\mathrm{CH_3CH_2CH(OH)CH_3}\); D = \(\mathrm{(CH_3)_3COH}\)
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