Question

Draw the product of the following reaction between propanoyl chloride and p-methoxynitrobenzene. Include formal charges.

Draw the product of the following reaction between propanoyl chloride and p-methoxynitrobenzene. Include formal charges.

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General guidance

Concepts and reason

Friedel craft acylation reaction is an electrophilic substitution reaction on aromatic rings, where the acyl cation acts as an electrophile in the process. This reaction process is catalyzed by a Lewis acid.

Fundamentals

General friedal craft acylation reaction

AlCI3+ R

Acylation reaction proceeds through three steps

1.Generation of electrophile from the acyl chloride

2.Electrophile substitution on aryl ring

3.Transfer of proton to regain aromaticity

Step-by-step

Step 1 of 2

1.Generation of electrophile from the acyl chloride

The given acyl chloride is propionyl chloride

Cl+AlCl3+AICl+ AlCl

Explanation | Common mistakes | Hint for next step

An electrophile has been generated from the Lewis acid and the given acyl chloride. The Lewis acid abstracts the chloride ion from the acyl chloride and gives an acyl cation as well as a AlCl4\u2212{\\rm{AlC}}{{\\rm{l}}_{\\rm{4}}}^ - complex.

Step 2 of 2

2.Electrophile substitution on aryl ring

\u7530N10

3.Transfer of proton to attain aromiticity

HClAlCl4

The complete reaction is

AlCl3CI


An electrophile is substituted at the carbon position where the high electron density is located on the ring. Then, the aromatization process takes place to attain stability in the ring. Aromatization takes place through the transfer of adjacent protons to the ring. The proton is then abstracted by the halide ion, forms HCl{\\rm{HCl}} and a Lewis acid.

Answer

The complete reaction is

AlCl3CI

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