Which is the most likely product of bromination of 4-methylpent-2-ene with NBS and initiation by photolysis of a peroxide?
A
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B
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C
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D
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Solution
The correct option is B Allylic bromination is the most likely reaction with NBS, initiated by photolysis of peroxide. There are two possible H-abstraction sites, C1 and C4 for the given molecule; Preferentially abstration of the tertiary H from C4 gives the more substituted allylic radical. The formed allylic radical will undergo delocalisation and form more substituted alkene product as the major product.