Solution

ID: past-exam-of-the-chemistry-b-course-of-the-university-of-cambridge/2025/paper-2/b10/a/i/solution

Use C1 for the carbonyl carbon, C2 for the adjacent carbon, and C3 for the beta carbon of the reactive enone fragment . water adds conjugately at C3, giving a beta-hydroxy ketone. The oxygen lone pair of neutral water attacks C3; move the C2=C3 pi pair toward C1–C2 and the carbonyl pi pair onto oxygen. This produces the charge-separated enolate–oxonium intermediate
A second water molecule can relay a proton from the newly attached oxonium oxygen to the enolate system. Using the carbon-centered resonance structure, reform C1=O and protonate C2 while the donating O–H bond returns its pair to the added oxygen. Equivalently, oxygen protonation first gives an enol, followed by water-mediated keto-enol tautomerism. Either path yields a neutral beta-hydroxy ketone and regenerates the relay water. There is no need to introduce externally supplied H or OH; solvent molecules perform the proton transfers. The uncatalyzed charge separation has a large barrier, so this mechanism describes a slow formal pathway, not a claim of rapid hydration in pure water.
Figure 1.
Reactive-fragment mechanisms for conjugate hydration, steroid reduction and finasteride trapping
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