SME
Organic Chemistry II
Carboxylic acid derivatives
Use this for “Rank methyl ethanoate, ethanoyl chloride and ethanamide by how fast each reacts with water.”
Put in order
Order from most to least reactive toward a nucleophile.
1
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2
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3
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4
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5
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6
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Assumptions
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Each derivative reacts by adding the nucleophile to the C=O carbon, then pushing out the group joined to it.
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The weaker the leaving group is as a base (Cl⁻ weakest, then RCOO⁻, RS⁻, RO⁻, H₂N⁻), the more reactive the derivative.
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An N or O next to the C=O shares its lone pair with it, which makes that carbon less open to attack; a carboxylate’s charge repels nucleophiles.
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A derivative can be made from any one above it, never from one below.
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