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Q80.

Expert-verified
Organic Chemistry
Found in: Page 382

Short Answer

Question: Draw a stepwise mechanism for the following reaction.

Answer

The stepwise mechanism of the given reaction is shown hereunder.

Mechanism

See the step by step solution

Step by Step Solution

Step-by-Step solutionStep 1: Proton transfer reaction 

The base transfers its electron density to the acidic hydrogen and abstracts it from the acidic compound.

Step 2: Ring-opening reaction

Upon undergoing the proton transfer reaction, the nucleophilic site thus formed on the then acid attacks the carbon attached to the electronegative atom. During this step, the ring opens.

Step 3: Mechanism of the given reaction

NaOH attacks on the acidic hydrogen, i.e., the one attached to the oxygen atom. The newly formed carbanion species then attacks the carbon attached to the highly electronegative atom.

Thus, the ring breaks and an epoxide is formed. The mechanism of the given reaction is shown hereunder

Mechanism

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