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Alcohols Phenols and Ethers question

2021 · 26 Feb · Shift 1 · Q13
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Alcohols Phenols and Ethers question

2021 · 26 Feb · Shift 1 · Q13

JEE MainChemistryAlcohols Phenols and EthersMCQ+4 / −1
JEE Main 2021 (Online) 26th February Morning Shift Chemistry - Alcohols, Phenols and Ethers Question 107 English B reacts with Hydroxyl amine but does not give Tollen's test. Identify A and B.
  1. A
    1, 1-Dichlorobutane and Butanal
  2. B
    2, 2-Dichlorobutane and Butan-2-one
  3. C
    1, 1-Dichlorobutane and 2-Butanone
  4. D
    2, 2-Dichlorobutane and Butanal
View written solutionFree

Correct answer: B

  1. We are told that B reacts with hydroxylamine but does not give Tollens' test.

  2. Reaction with hydroxylamine: Hydroxylamine, NH2OHNH_2OHNH2​OH, reacts with carbonyl compounds to form oximes. So BBB must be either:

    • an aldehyde, or
    • a ketone.
  3. Tollens' test:

    • Aldehydes generally give a positive Tollens' test.
    • Ketones generally do not give Tollens' test.

    Therefore, since BBB does not give Tollens' test, BBB must be a ketone.

  4. Among the given options:

    • Butanal = aldehyde
    • Butan-2-one / 2-butanone = ketone

    Hence, B=B =B= Butan-2-one (2-butanone).

  5. Now identify AAA. The question implies that AAA on hydrolysis/related transformation gives BBB.

    • A gem-dihalide of type R2CCl2R_2CCl_2R2​CCl2​ on hydrolysis gives a ketone.
    • A gem-dihalide of type RCHCl2RCHCl_2RCHCl2​ on hydrolysis gives an aldehyde.
  6. Check the structures:

    • 1,1-Dichlorobutane has both Cl on terminal carbon: CH3CH2CH2CHCl2CH_3CH_2CH_2CHCl_2CH3​CH2​CH2​CHCl2​ On hydrolysis, this gives: CH3CH2CH2CHOCH_3CH_2CH_2CHOCH3​CH2​CH2​CHO which is butanal (aldehyde).

    • 2,2-Dichlorobutane has both Cl on second carbon: CH3CCl2CH2CH3CH_3CCl_2CH_2CH_3CH3​CCl2​CH2​CH3​ On hydrolysis, this gives: CH3COCH2CH3CH_3COCH_2CH_3CH3​COCH2​CH3​ which is butan-2-one (ketone).

  7. Since BBB must be butan-2-one, the corresponding AAA is 2,2-dichlorobutane.

  8. Therefore the correct pair is: A=2,2-Dichlorobutane,B=Butan-2-oneA = 2,2\text{-Dichlorobutane}, \quad B = \text{Butan-2-one}A=2,2-Dichlorobutane,B=Butan-2-one

  9. Option check:

    • A: 1,11,11,1-Dichlorobutane and Butanal ❌ (aldehyde gives Tollens' test)
    • B: 2,22,22,2-Dichlorobutane and Butan-2-one ✅
    • C: 1,11,11,1-Dichlorobutane and 2-Butanone ❌ (mismatch in conversion)
    • D: 2,22,22,2-Dichlorobutane and Butanal ❌

So, the correct answer is B.

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