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(a) Design an alkyl halide that will give only 2,4-diphenylpent-2-ene upon treatment

Chapter 7, Problem 7-65

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QUESTION:

(a) Design an alkyl halide that will give only 2,4-diphenylpent-2-ene upon treatment with potassium tert-butoxide (a bulky base that promotes E2 elimination). (b) What stereochemistry is required in your alkyl halide so that only the following stereoisomer of the product is formed? C C CH(Ph)CH3

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QUESTION:

(a) Design an alkyl halide that will give only 2,4-diphenylpent-2-ene upon treatment with potassium tert-butoxide (a bulky base that promotes E2 elimination). (b) What stereochemistry is required in your alkyl halide so that only the following stereoisomer of the product is formed? C C CH(Ph)CH3

ANSWER:

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We need to design an alkyl halide that will give only 2,4-diphenyl-2-ene upon treatment with potassium tert-butoxide and stereochemistry is required in your alkyl halide so that only the following stereoisomer of the product is formed.

If the base is  bulky it promotes E2 elimination.

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