Verified Solution • 2025–26 Session moderate

QNEET-2024-Ch-7: NEET 2024 Chemistry - Class 12 NEET-2024-Ch-7 Solution: Identify the correct reagents that would bring about the…

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

Multiple Choice Options

  • A (i) H2O/H+\mathrm{H}_2\mathrm{O} / \mathrm{H}^{+} (ii) CrO3\mathrm{CrO}_3
  • B (i) BH3\mathrm{BH}_3 (ii) H2O2/OH−\mathrm{H}_2\mathrm{O}_2 / \mathrm{OH}^- (iii) PCC\mathrm{PCC}
  • C (i) BH3\mathrm{BH}_3 (ii) H2O2/OH−\mathrm{H}_2\mathrm{O}_2 / \mathrm{OH}^- (iii) alk. KMnO4\mathrm{KMnO}_4
  • D (i) H2O/H+\mathrm{H}_2\mathrm{O} / \mathrm{H}^{+} (ii) PCC\mathrm{PCC}

Step-by-Step Verified Solution

Explanation:

  1. Hydroboration-Oxidation (Anti-Markovnikov Hydration):
  2. Treatment of the terminal alkene with BH3\text{BH}_3 followed by H2O2/OH−\text{H}_2\text{O}_2/\text{OH}^- adds −H-\text{H} and −OH-\text{OH} across the double bond in an anti-Markovnikov fashion (syn-addition):
  3. R−CH=CH2→(i) BH3,  (ii) H2O2/OH−R−CH2−CH2OH(1∘ alcohol)\text{R}-\text{CH}=\text{CH}_2 \xrightarrow{\text{(i) } \text{BH}_3,\; \text{(ii) } \text{H}_2\text{O}_2/\text{OH}^-} \text{R}-\text{CH}_2-\text{CH}_2\text{OH}\quad (1^\circ \text{ alcohol})
  4. Selective Oxidation to Aldehyde:
  5. Oxidation of this primary alcohol using Pyridinium chlorochromate (PCC\text{PCC}) selectively stops at the aldehyde stage without over-oxidizing to a carboxylic acid:
  6. R−CH2−CH2OH→PCCR−CH2−CHO\text{R}-\text{CH}_2-\text{CH}_2\text{OH} \xrightarrow{\text{PCC}} \text{R}-\text{CH}_2-\text{CHO}

Why the other pathways fail:

  1. Acid-catalyzed hydration (H2O/H+\text{H}_2\text{O}/\text{H}^+) follows Markovnikov's rule (forming a 2∘2^\circ carbocation/alcohol), which on oxidation gives a ketone rather than an aldehyde.
  2. Alkaline KMnO4\text{KMnO}_4 is a strong oxidizing agent that would oxidize a primary alcohol directly to a carboxylic acid (−COOH-\text{COOH}) instead of stopping at an aldehyde (−CHO-\text{CHO}).


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