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Why does an amide carbonyl absorb lower than a ketone's?

  • A.Amide groups are always conjugated with a ring
  • B.The nitrogen donates electron density into the bond
  • C.Amides are more strongly hydrogen bonded
  • D.The nitrogen atom increases the reduced mass

Answer: B

The nitrogen's lone pair delocalises into the carbonyl, reducing its double bond character and dropping the band to about 1650 against a ketone's 1715. Hydrogen bonding contributes a little more, reduced mass is barely affected, and no ring is required. Ordering the carbonyl derivatives by how much the adjacent atom donates or withdraws - anhydride highest, amide lowest - turns a list of numbers into a pattern. A limit that survives making every external component ideal is an intrinsic one, and worth knowing for that reason.

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