Show how you would use the Friedel–Crafts acylation, Clemmensen reduction, and/or Gatterman–Koch synthesis to prepare the following compounds:
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Step 1: Begin with benzene as the starting material. Use Friedel–Crafts acylation to introduce an acetyl group (-COCH3) onto the benzene ring. This reaction requires an acyl chloride (CH3COCl) and a Lewis acid catalyst such as AlCl3.

Step 2: Perform a Clemmensen reduction to convert the ketone group (-COCH3) introduced in the previous step into an alkyl group (-CH2CH3). This reduction is carried out using zinc amalgam (Zn(Hg)) and concentrated hydrochloric acid (HCl).

Step 3: Introduce the amine group (-NH2) onto the benzene ring. This can be achieved by nitration of the benzene ring (using HNO3 and H2SO4) followed by reduction of the nitro group (-NO2) to an amine (-NH2) using a reducing agent such as Sn/HCl or Fe/HCl.

Step 4: Convert the amine group (-NH2) into an amide group (-NHCOCH3) by reacting it with acetic anhydride (CH3CO)2O. This step forms the first amide bond on the benzene ring.

Step 5: Finally, introduce the second amide group (-NHCOCH3) onto the benzene ring by reacting the amine group with another equivalent of acetic anhydride. This completes the synthesis of the target compound.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Friedel–Crafts Acylation

Friedel–Crafts acylation is an electrophilic aromatic substitution reaction that introduces an acyl group into an aromatic ring. This reaction typically uses an acyl chloride and a Lewis acid catalyst, such as aluminum chloride, to generate the acylium ion, which then reacts with the benzene ring. This method is crucial for synthesizing aromatic ketones, which are often precursors for further functionalization.

Clemmensen Reduction

The Clemmensen reduction is a chemical reaction that reduces carbonyl groups (aldehydes and ketones) to methylene groups (alkanes) using zinc amalgam and hydrochloric acid. This reaction is particularly useful for converting aromatic ketones into aliphatic compounds, making it a valuable tool in organic synthesis when other reduction methods are not suitable due to the presence of sensitive functional groups.

Gatterman–Koch Synthesis

The Gatterman–Koch synthesis is a method for synthesizing aromatic aldehydes from aromatic compounds using carbon monoxide and hydrochloric acid in the presence of a Lewis acid catalyst, typically aluminum chloride. This reaction allows for the introduction of formyl groups into aromatic rings, which can be further transformed into various functional groups, making it a versatile approach in organic synthesis.

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