Question

A graduate student was assigned to synthesize compound A starting from cyclohexanone. Said graduate reacted phenyl Grignard (C6H5MgBr) with ethylene oxide to give the primary alcohol that he then converted to the alkyl bromide with PBr3. The resulting alkyl bromide was converted to another Grignard and reacted with cyclohexanone to give tertiary alcohol. Unfortunately, this alcohol dehydrated to give B as the major product.

a. draw the reaction scheme to explain how they went wrong.
b. draw a new route to get A that will avoid B. You need to cyclohexanone and any carbon-containing compounds that this student used as well as any inorganic reagents necessary.

Answer 1

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