A student adds NBS to a solution of 1-methylcyclohexene and irradiates the mixture with a sunlamp until all the NBS has reacted. After a careful distillation, the product mixture contains two major products of formula C7H11Br.
(a) Draw the resonance forms of the three possible allylic free radical intermediates.
(b) Rank these three intermediates from least stable to most stable.
(c) Draw the products obtained from each free-radical intermediate.
(d) The two major products are the ones with the most stable double bonds that result from the two most stable intermediates. Indicate the compounds that are likely to be the major products.
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