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Aldehydes Ketones and Carboxylic Acids question

2021 · 24 Feb · Shift 2 · Q5
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  5. /2021 · 24 Feb · Shift 2 · Q5

Aldehydes Ketones and Carboxylic Acids question

2021 · 24 Feb · Shift 2 · Q5

JEE MainChemistryAldehydes Ketones and Carboxylic AcidsMCQ+4 / −1
Which one of the following carbonyl compounds cannot be prepared by addition of water on an alkyne in the presence of HgSO4HgSO_4HgSO4​ and H2SO4H_2SO_4H2​SO4​?
  1. A
    JEE Main 2021 (Online) 24th February Evening Shift Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 158 English Option 1
  2. B
    JEE Main 2021 (Online) 24th February Evening Shift Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 158 English Option 2
  3. C
    JEE Main 2021 (Online) 24th February Evening Shift Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 158 English Option 3
  4. D
    JEE Main 2021 (Online) 24th February Evening Shift Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 158 English Option 4
View written solutionFree

Correct answer: C

  1. Reaction involved: hydration of alkynes in presence of HgSO4/H2SO4HgSO_4/H_2SO_4HgSO4​/H2​SO4​

    In acidic mercuric sulfate catalyzed hydration, water adds across the triple bond of an alkyne to first give an enol, which then undergoes keto-enol tautomerism to give a carbonyl compound.

  2. Products formed from different alkynes

    • For a terminal alkyne R−C≡CHR{-}C\equiv CHR−C≡CH: R−C≡CH→H2SO4HgSO4, H2OR−CO−CH3R{-}C\equiv CH \xrightarrow[H_2SO_4]{HgSO_4,\ H_2O} R{-}CO{-}CH_3R−C≡CHHgSO4​, H2​OH2​SO4​​R−CO−CH3​ So terminal alkynes give methyl ketones.

    • For acetylene HC≡CHHC\equiv CHHC≡CH: HC≡CH→H2SO4HgSO4, H2OCH3CHOHC\equiv CH \xrightarrow[H_2SO_4]{HgSO_4,\ H_2O} CH_3CHOHC≡CHHgSO4​, H2​OH2​SO4​​CH3​CHO This gives ethanal.

    • For an internal alkyne: hydration gives a ketone (or mixture of ketones if unsymmetrical).

  3. Important conclusion

    By this method, the obtainable carbonyl compounds are:

    • ketones
    • ethanal as the only aldehyde obtainable from acetylene

    Therefore, any aldehyde other than ethanal cannot be prepared by this method.

  4. Hence

    Among the given options, the correct one must be the compound corresponding to an aldehyde other than ethanal, which is Option C.

  5. Comparison with stored answer

    Stored correct answer = C

    Our derived answer = C

    So they agree.

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