Complete these mechanisms by drawing the structure of the products in each case. The product of (a) and the size of the new ring formed in (b) are respectively :
(a)
(b)

Question

Complete these mechanisms by drawing the structure of the products in each case. The product of (a) and the size of the new ring formed in (b) are respectively : (a) (b)

TestHub · Accepted Answer

(a) The HO - ion removes the -OH proton. The resulting alkoxide then forms a C=O bond, while the C-H bond pair from the carbinol carbon moves (along with H) to the carbon bearing the chlorine atom, and Cl - leaves. The products are acetone, H 2 O, and Cl - . (b) The tethered amine undergoes an intramolecular 6-exo-trig cyclization, adding to the far carbon of the C=C bond. The π electrons shift towards the C-Br carbon, and Br - leaves. Subsequent loss of the N-H proton yields the fused bicyclic amine and HBr. Answer: (C).

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