Which of the following reactions is NOT correctly represented?
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Answer
(1) [figure]
Solution
(1) The ring is 3-methylcyclohexene: the CH3 is on the ring carbon next to the C=C. With Br2/h , free-radical substitution occurs at the allylic position; the tertiary H on the ring carbon carrying CH3 is both tertiary and allylic, so Br enters the ring (allylic) carbon, not the primary CH3 group. The product shown is not correct.
(2) Sandmeyer reaction: C6H5N2+Cl- Cu2Br2/HBr C6H5Br + N2 correct.
(3) Toluene with Br2/h : side-chain (benzylic) free-radical substitution gives benzyl bromide correct.
(4) Toluene with Br2/Fe in the dark: electrophilic ring substitution; -CH3 is o/p-directing o- and p-bromotoluenes correct.
Answer: (1)