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Topic: Aldehydes and ketones: HCN, NH3 derivatives, Grignard, oxidation, reduction (Wolff-Kishner, Clemmensen)· Organic Compounds Containing Oxygen

Identify the correct reagents that would bring about the following transformation.[structure transformation shown in figure: ring-CH_2-CH=CH_2 → ring-CH_2-CH_2-CHO]

Identify the correct reagents that would bring about the following transformation.

[structure transformation shown in figure: ring-CH\(_2\)-CH=CH\(_2\) \(\rightarrow\) ring-CH\(_2\)-CH\(_2\)-CHO]

reaction scheme: ring-CH2-CH=CH2 to ring-CH2-CH2-CHO

1. (i) \(H_2O/H^+\) (ii) PCC

2. (i) \(H_2O/H^+\) (ii) \(CrO_3\)

3. (i) \(BH_3\) (ii) \(H_2O_2/\overset{\ominus}{O}H\) (iii) PCC

4. (i) \(BH_3\) (ii) \(H_2O_2/\overset{\ominus}{O}H\) (iii) alk. \(KMnO_4\) (iv) \(H_3O^{\oplus}\)

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Answer: 3. (i) \(BH_3\) (ii) \(H_2O_2/\overset{\ominus}{O}H\) (iii) PCC

Key idea: the \(\mathrm{-CH=CH_2}\) group must become \(\mathrm{-CH_2CH_2CHO}\), a terminal aldehyde, which needs anti-Markovnikov addition of water.

  1. \(\mathrm{BH_3}\) then \(\mathrm{H_2O_2/OH^-}\) (hydroboration-oxidation) gives the primary alcohol \(\mathrm{-CH_2CH_2CH_2OH}\).
  2. PCC oxidises a primary alcohol to the aldehyde and stops there.

Options 1 and 2 use acid hydration (Markovnikov, secondary alcohol). Option 4 oxidises to the carboxylic acid. Option 3 is correct.

Doubtly AI · 30 Oct 2026 AI-generated · not yet verified Report
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