Chemistry · Organic Reaction Mechanisms
According to the Hard-Soft Acid-Base (HSAB) principle, what are the major products A and B formed when an amine group (-NH 2 ) and a thiol group (-SH) respectively react with an α,β-unsaturated carbonyl compound in the presence of a strong base like NaH?
Verified Solution4 OptionsUpdated: October 2026👁️1 View
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- 1Product A is formed by the attack of the nitrogen nucleophile at the β-carbon, and Product B is formed by the attack of the sulfur nucleophile at the carbonyl carbon.
- 2Product A is formed by the attack of the hard nitrogen nucleophile at the carbonyl carbon, and Product B is formed by the attack of the soft sulfur nucleophile at the β-carbon.✓
- 3Both A and B are formed by nucleophilic attack at the β-carbon (soft electrophilic center).
- 4Both A and B are formed by nucleophilic attack at the carbonyl carbon (hard electrophilic center).
Correct answer
Product A is formed by the attack of the hard nitrogen nucleophile at the carbonyl carbon, and Product B is formed by the attack of the soft sulfur nucleophile at the β-carbon.
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