Solution

ID: past-exam-of-the-chemistry-course-of-the-year-1-of-the-natural-sciences-course-of-the-university-of-cambridge/2021/paper-1/1/a/solution

A: conjugated ester; B: unconjugated ester; C: terminal alkyne acetal.
A has a strong ester C=O band at roughly –, lowered by conjugation with C=C. B's unconjugated ester carbonyl is nearer –; it also has terminal-alkene features, including the approximately pair.
C has no carbonyl band. Its terminal alkyne gives a relatively sharp sp C-H stretch near and a usually weaker C≡C feature near –. C-O stretching alone is less diagnostic because esters and the acetal all contain C-O bonds. The numbers are characteristic ranges, not exact frequencies inferred from an unprinted IR trace.

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