Q10 (a) The following reaction does not produce the desired product A but produce a side product B. Propose a reaction mechanism for the formation of B. (Hint: these are tautomerizations) (b) Why is B observed instead of A? Explain briefly. OH 1) NaNHz 2) Mel A OH B

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**Question 10**

(a) The following reaction does not produce the desired product A but produces a side product B. Propose a reaction mechanism for the formation of B. (Hint: these are tautomerizations)

(b) Why is B observed instead of A? Explain briefly.

**Reaction Details:**

- Starting Material: Cyclohexanol derivative with an alkyne group
- Reagents:
  1) Sodium amide (NaNH₂)
  2) Methyl iodide (MeI)

- Desired Product (A): Cyclohexanol derivative with an alkyne group

- Observed Side Product (B): Cyclohexanone derivative with an alkyne group (tautomerization to a ketone)
Transcribed Image Text:**Question 10** (a) The following reaction does not produce the desired product A but produces a side product B. Propose a reaction mechanism for the formation of B. (Hint: these are tautomerizations) (b) Why is B observed instead of A? Explain briefly. **Reaction Details:** - Starting Material: Cyclohexanol derivative with an alkyne group - Reagents: 1) Sodium amide (NaNH₂) 2) Methyl iodide (MeI) - Desired Product (A): Cyclohexanol derivative with an alkyne group - Observed Side Product (B): Cyclohexanone derivative with an alkyne group (tautomerization to a ketone)
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