The products of allyic bromination reaction are particularly useful for conversion into dienes by dehydrohalogenation with base. Cyclohexene can be converted into 1,3-clohexadiene, for example.
What products would you expect from reaction of 4,4-dimethylcyclohexene with NBS?
Strategy draw the alkene reaction, and identify the allylic positions. In this case, there are two different allyic positions; well all labe them a and b. now abstract an ally hydrogen from each position to generate the two corresponding allyic radicals. Each of the two ally radicals can add a br atom at either end (a or a ; b or b)} to give a mixture of up to four products. Draw and name the products. In the present instance, the “two” products from reaction at position b are identical, so a total of only three products are formed in this reaction
The products of allyic bromination reaction are particularly useful for conversion into dienes by dehydrohalogenation with base. Cyclohexene can be converted into 1,3-clohexadiene, for example.
What products would you expect from reaction of 4,4-dimethylcyclohexene with NBS?
Strategy draw the alkene reaction, and identify the allylic positions. In this case, there are two different allyic positions; well all labe them a and b. now abstract an ally hydrogen from each position to generate the two corresponding allyic radicals. Each of the two ally radicals can add a br atom at either end (a or a ; b or b)} to give a mixture of up to four products. Draw and name the products. In the present instance, the “two” products from reaction at position b are identical, so a total of only three products are formed in this reaction
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