Verified Solution • 2025–26 Session
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QNEET-2024-Ch-3: NEET 2024 Chemistry - Class 12 NEET-2024-Ch-3 Solution: Major products A and B formed in the following reaction…
Major products A and B formed in the following reaction sequence are
Multiple Choice Options
- A https://pub-09328fb7cd7b4b94aaf562e6bb66ceaf.r2.dev/photos/2f6c7ea8662a0ae72f0d40a6f2dc1af287de1450aea555d83a94b8cef1c20c92.webp
- B https://pub-09328fb7cd7b4b94aaf562e6bb66ceaf.r2.dev/photos/c76ed9ebd857913c7a10ab92e5ef6fc18796746259735f511ca85dbffc43c35b.webp
- C https://pub-09328fb7cd7b4b94aaf562e6bb66ceaf.r2.dev/photos/96cbf12ce03b87e165f41209d30dbba6fa44f003c8cac6dd41c6a0f18e227127.webp
- D https://pub-09328fb7cd7b4b94aaf562e6bb66ceaf.r2.dev/photos/50489c95003809da538df5c8049700b94ffd7f8e67bb284f2877445f3b3c3474.webp
Step-by-Step Verified Solution
**Core Concept & Governing Principle**
The reaction sequence involves (i) oxidation of a primary alcohol to an aldehyde, (ii) nucleophilic addition of phenol to the aldehyde forming a benzylic ether, and (iii) further oxidation of the benzylic carbon to a carboxylic acid which then undergoes intramolecular esterification (lactonisation). The major products are determined by the most favourable oxidation state changes and the stability of the intermediates.
**Step 1: Identify the functional groups in the starting material**
The substrate contains a primary –CH₂OH group attached to an aromatic ring bearing a phenolic –OH group.
**Step 2: First oxidation (e.g., PCC, Swern, or Na₂Cr₂O₇/H₂SO₄)**
Primary alcohol → aldehyde.
The phenolic –OH remains unchanged under these conditions.
**Step 3: Nucleophilic addition of the phenolic oxygen to the aldehyde**
The phenolic oxygen attacks the electrophilic carbonyl carbon of the newly formed aldehyde, giving a hemi‑acetal (benzylic alkoxy‑alcohol).
Because the aromatic ring can delocalise the positive charge, this intermediate is relatively stable.
**Step 4: Further oxidation of the benzylic carbon**
A stronger oxidising agent (e.g., KMnO₄, Na₂Cr₂O₇/H₂SO₄) oxidises the benzylic carbon bearing the –O–Ar substituent from the alcohol oxidation level to a carboxylic acid.
**Step 5: Intramolecular esterification (lactone formation)**
The carboxylic acid and the adjacent phenolic oxygen are positioned ortho‑to‑each other on the same aromatic ring, allowing a favorable 5‑ or 6‑membered cyclic ester (lactone) to form with loss of water.
**Step 6: Identify the major products**
- **Product A**: The lactone obtained after cyclisation (major, thermodynamically favoured).
- **Product B**: The benzylic ether (hemi‑acetal) formed after the phenolic addition, which can be isolated if the oxidation is stopped prematurely.
These two structures correspond exactly to the structures shown in option **A**.
**Final Conclusion & Correct Option**
The major products of the described reaction sequence are the cyclic ester (lactone) and the benzylic ether shown in option **A**.