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The reactivity of a leaving group decreases as its basic nature increases. Arrange the following groups based on their basicity:

1. Amide ion (NH2−) > Alkoxide ion (OR−) > Carboxylate ion (RCOO−) > Chloride ion (Cl−)
2. Amide ion (NH2−) > Carboxylate ion (RCOO−) > Alkoxide ion (OR−) > Chloride ion (Cl−)
3. Chloride ion (Cl−) > Amide ion (NH2−) > Alkoxide ion (OR−) > Carboxylate ion (RCOO−)
4. Carboxylate ion (RCOO−) > Amide ion (NH2−) > Chloride ion (Cl−) > Alkoxide ion (OR−)

Correct answer: Amide ion (NH2−) > Alkoxide ion (OR−) > Carboxylate ion (RCOO−) > Chloride ion (Cl−)

Solution

The basicity of a leaving group inversely affects its ability to leave; more basic groups are less stable and less likely to leave. The order NH2− > OR− > RCOO− > Cl− correctly reflects decreasing basicity.

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