Question

Why only one mole of secondary amine reacts with diethyl oxalate? Whereas two moles of primary amines reacts with diethyl oxalate.

Answer 1

Answer:

Explanation:

1°, 2°, and 3° amines can be distinguished by their reactions with diethyl oxalate. Primary (1°) amines react with diethyl oxalate forming N,N-oxamide, which is a solid.

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Secondary (2°) amines react with diethyl oxalate forming oxamic ester, which is a liquid.

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Tertiary (3°) amines do not react with diethyl oxalate

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Answer 2

The tetrahedral intermediate in the primary amine attack case would have an intramolecular hydrogen bond to stabilize. In the secondary amine case, no such H-bond is available.

Also, the secondary amine group might have streic hinderance, which makes only one mole of secondary amine to react with diethyl oxalate

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