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Hydrocarbons question

2022 · Shift 2 · Q13
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Hydrocarbons question

2022 · Shift 2 · Q13

JEE AdvancedChemistryHydrocarbonsMultiple correct+4 / −2
Considering the following reaction sequence, the correct statement(s) is(are) JEE Advanced 2022 Paper 2 Online Chemistry - Hydrocarbons Question 5 English
  1. A
    Compounds P\mathbf{P}P and Q\mathbf{Q}Q are carboxylic acids.
  2. B
    Compound S\mathbf{S}S decolorizes bromine water.
  3. C
    Compounds P\mathbf{P}P and S\mathbf{S}S react with hydroxylamine to give the corresponding oximes.
  4. D
    Compound R\mathbf{R}R reacts with dialkylcadmium to give the corresponding tertiary alcohol.
View written solutionFree

Correct answer: A, C

  1. Identify the likely transformations in the sequence

    The options themselves strongly indicate the nature of the compounds:

    • Option C says P\mathbf{P}P and S\mathbf{S}S react with hydroxylamine to give oximes. Only aldehydes and ketones form oximes with hydroxylamine.
    • Therefore, P\mathbf{P}P and S\mathbf{S}S must be carbonyl compounds (aldehyde/ketone), not carboxylic acids.
    • Hence option A (that both P\mathbf{P}P and Q\mathbf{Q}Q are carboxylic acids) is inconsistent if P\mathbf{P}P forms an oxime.
  2. Test each option using standard organic reactions

    Option A: P\mathbf{P}P and Q\mathbf{Q}Q are carboxylic acids.

    • Carboxylic acids do not react with hydroxylamine to give oximes.
    • Since option C explicitly says P\mathbf{P}P gives an oxime, P\mathbf{P}P cannot be a carboxylic acid.
    • Therefore A is false.

    Option B: Compound S\mathbf{S}S decolorizes bromine water.

    • Bromine water is decolorized by compounds containing C=C\mathrm{C=C}C=C unsaturation or some strongly activated systems.
    • But if S\mathbf{S}S reacts with hydroxylamine to form an oxime, then S\mathbf{S}S is most likely an aldehyde/ketone.
    • Ordinary aldehydes/ketones do not decolorize bromine water by addition like alkenes.
    • Therefore B is false.

    Option C: Compounds P\mathbf{P}P and S\mathbf{S}S react with hydroxylamine to give the corresponding oximes.

    • Aldehydes and ketones react with hydroxylamine: R2C=O+NH2OH→R2C=NOH+H2OR_2C=O + NH_2OH \rightarrow R_2C=NOH + H_2OR2​C=O+NH2​OH→R2​C=NOH+H2​O
    • This is the standard oxime formation reaction.
    • Thus C is true.

    Option D: Compound R\mathbf{R}R reacts with dialkylcadmium to give the corresponding tertiary alcohol.

    • Dialkylcadmium reagents are less reactive organometallics and are known to react with acid chlorides to give ketones, not tertiary alcohols.
    • Tertiary alcohols are usually obtained by reaction of Grignard reagents/organolithium with ketones or esters (with excess reagent), not by dialkylcadmium directly.
    • Therefore D is false.
  3. Final selection

    The only statement that must be correct is: C only\boxed{\text{C only}}C only​

  4. Comparison with stored answer

    • Stored correct answer: A, C
    • Derived answer: C only

    These do not match. Since P\mathbf{P}P forms an oxime (from option C), it cannot be a carboxylic acid, so option A cannot be correct.

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