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Question #44134

Difficulty: 8/10 | 🟢 Free

The Question

Consider the following reaction sequence:

$\ce{4-vinylbenzonitrile ->[1. 9-BBN, THF, 0^{\circ}C][2. H_2O_2 (excess), NaOH (aq), 50^{\circ}C] P}$

Identify the major organic product $P$ .

Options

A.
4-(2-hydroxyethyl)benzamide
B.
4-(2-hydroxyethyl)benzonitrile
C.
4-(1-hydroxyethyl)benzamide
D.
4-(2-hydroxyethyl)benzoic acid

Check Your Answer

Correct Answer

Step-by-Step Solution

Explanation

How the Examiner Thinks

Exception_Exposure

Learn to identify edge cases and boundary exceptions that JEE examiners hide in math problems.

Concepts Behind This Question

Peroxy Linkage Identification|Hydroboration-Oxidation Logic|Reduction Selectivity (Hydrides)

Why This Question Is Tricky

Common Mistakes

This problem tests the student's understanding of the dual reactivity of the hydroperoxide ion ( $\ce{HOO^-}$ ) in the oxidation phase of the hydroboration-oxidation sequence.

The 'hidden variable' is the chemoselectivity trap: while $\ce{HOO^-}$ successfully oxidizes the alkylborane to an alcohol, its enhanced nucleophilicity (due to the $\alpha$ -effect) simultaneously triggers the Radziszewski reaction on the unprotected nitrile group under the same alkaline conditions.

Students who rote-learn the reagent as a simple 'alkene to anti-Markovnikov alcohol' converter will fail to account for the concurrent transformation of the nitrile into an amide, incorrectly selecting the unreacted nitrile distractor.

Quick Facts About This Question

Question Information

Subject	Chemistry
Chapter	Redox Reactions - Class 11 Part 2
Concept	Peroxy Linkage Identification
Difficulty	8
Cognitive Load	7
Target Solve Time	160 sec
Access	Free