Question about malonic ester synthesis

[bullsfan1986]

The question reads as:

Which of the following halides would be the most suitable starting material for a malonic ester synthesis of dibenzylacetic acid?

a) bromobenzene

b)2-chlorophenol

c) 4-chlorophenol

d) benzyl bromide

the correct answer is d.

I eliminated b and c right away but I'm having a hard time understanding why choice a is incorrect. Thanks in advance.

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[Bali]

d is correct

look at the structure of dibenzylacetic acid....i think you're making the same mistake i did when i first saw this.

 

[Rabolisk]

Because benzyl bromide is not the same thing as bromobenzene, which is phenyl bromide. You're synthesizing dibenzylacetic acid not diphenylacetic acid.

 

[bullsfan1986]

ah, drawing it out helped. thanks guys.