Question #8533e

1 Answer
Truong-Son N.
Aug 27, 2017

I got #D#.

You should look up this sequence of reactions to understand these more:

  • Friedel-Crafts acylation
  • Aromatic bromination (reactions of substituted benzenes)
  • Wolff-Kishner reduction (in base)

Beyond that, I can go into more detail below.

The overall synthesis would be:

The Friedel-Crafts acylation turns the acetyl chloride into an electrophile using a strong Lewis acid, #"AlCl"_3# (this is the slow step). Benzene then acts as a nucleophile, later patched up by a #beta#-elimination.

The aromatic bromination is influenced by the acyl group, which is a meta director. The #"Br"_2# forms a #"Br"_2-"FeBr"_3# acid-base adduct (this is likely te slow step). That allows #"Br"^(+)# to be an electrophile, which is then going to add meta to the acyl group.

The Wolff-Kishner mechanism is quite long... It essentially turns a ketone into an alkane (removing the carbonyl) and releases #"N"_2(g)#. Here is a general one for acetone:

Thus, we obtain the product given for #D#.

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