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Solved: Propose an efficient synthesis for the following
Chapter 18, Problem 18.55(choose chapter or problem)
Propose an efficient synthesis for the following transformation: Br
Questions & Answers
QUESTION:
Propose an efficient synthesis for the following transformation: Br
ANSWER:Step 1 of 2
Reaction with bromobenzene with magnesium metal inserts the magnesium between the benzene carbon and the bromine atom, forming PhMgBr. Because of the relative electronegativities of carbon and magnesium, the Grignard reagent possesses a strong negative charge character on the carbon atom attached to the magnesium. This makes it a strong nucleophile. Reaction of this Grignard reagent with acetaldehyde forms a secondary alkoxide, which is quenched with water to yield the secondary alcohol intermediate.