Solution

ID: past-exam-of-the-chemistry-course-of-the-year-1-of-the-natural-sciences-course-of-the-university-of-cambridge/2022/paper-1/1/a/i/solution

A is 3-Chlorobutan-2-one, . Counting chlorine as one hydrogen in the index of index of hydrogen deficiency gives . A single carbonyl accounts for that unsaturation; the resonance at ppm identifies a ketone, while the ppm methine bears chlorine.
The carbon-13 NMR assignments are for , for , for and ppm for . The four distinct carbon environments agree with the unsymmetrical structure. The small signal near 77 ppm belongs to the usual deuterated chloroform solvent, rather than to a fifth carbon of A.

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