Question

Question #8533e

Answer 1

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.

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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`.