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Aldehydes Ketones and Carboxylic Acids question

2004 · Shift 0 · Q17
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Aldehydes Ketones and Carboxylic Acids question

2004 · Shift 0 · Q17

JEE MainChemistryAldehydes Ketones and Carboxylic AcidsMCQ+4 / −1
Which one of the following reduced with zinc and hydrochloric acid to give the corresponding hydrocarbon?
  1. A
    Ethyl acetate
  2. B
    Butan -2-one
  3. C
    Acetamide
  4. D
    Acetic acid
View written solutionFree

Correct answer: B

  1. We need to identify which compound gives the corresponding hydrocarbon on reduction with zinc and hydrochloric acid.

  2. The reagent combination Zn/HCl is used in Clemmensen reduction, which reduces: Aldehydes and ketones⟶hydrocarbons\text{Aldehydes and ketones} \longrightarrow \text{hydrocarbons}Aldehydes and ketones⟶hydrocarbons

    In general: R−CO−R′→HClZn(Hg)R−CH2−R′R-CO-R' \xrightarrow[\text{HCl}]{\text{Zn(Hg)}} R-CH_2-R'R−CO−R′Zn(Hg)HCl​R−CH2​−R′

    Even when written as Zn/HCl in such questions, the intended reaction is the Clemmensen-type reduction of the carbonyl group.

  3. Now check each option:

    A. Ethyl acetate

    • It is an ester: CH3COOC2H5CH_3COOC_2H_5CH3​COOC2​H5​
    • Esters are not reduced to hydrocarbons by Zn/HCl.
    • So, incorrect.

    B. Butan-2-one

    • It is a ketone: CH3COCH2CH3CH_3COCH_2CH_3CH3​COCH2​CH3​
    • Ketones undergo Clemmensen reduction to hydrocarbons: CH3COCH2CH3→HClZnCH3CH2CH2CH3CH_3COCH_2CH_3 \xrightarrow[\text{HCl}]{\text{Zn}} CH_3CH_2CH_2CH_3CH3​COCH2​CH3​ZnHCl​CH3​CH2​CH2​CH3​
    • Product is butane, the corresponding hydrocarbon.
    • So, correct.

    C. Acetamide

    • It is an amide: CH3CONH2CH_3CONH_2CH3​CONH2​
    • Amides do not give the corresponding hydrocarbon with Zn/HCl.
    • So, incorrect.

    D. Acetic acid

    • It is a carboxylic acid: CH3COOHCH_3COOHCH3​COOH
    • Carboxylic acids are not reduced to hydrocarbons by Zn/HCl.
    • So, incorrect.
  4. Therefore, the only compound that gives the corresponding hydrocarbon on reduction with Zn/HCl is: Butan-2-one\boxed{\text{Butan-2-one}}Butan-2-one​

  5. Comparison with stored correct answer:

    • Derived answer: B
    • Stored correct answer: B
    • They match.
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