Carboxylic Acid to Acid Chloride Practice Problems

Phosgene (COCl₂) is a toxic gas used as a chemical weapon. Identify the product formed by the reaction of phosgene with acetic acid.

The reaction of pentanedioic acid with thionyl chloride results in an anhydride instead of an acyl chloride. Provide the mechanism for the formation of the anhydride.

Draw the mechanism for the reaction of 3-methylbutanoic acid and oxalyl chloride to form 3-methylbutanoyl chloride. The mechanism is similar to that of the reaction of thionyl chloride (SOCl₂) with a carboxylic acid. It starts with the formation of a mixed acid anhydride intermediate. This anhydride undergoes nucleophilic acyl substitution by the chloride ion, to remove the leaving group which further breaks into carbon dioxide, carbon monoxide, and chloride ion.

Show the missing reagents in the given synthesis.

Draw the expected product for the given reaction.

Give the final product of the reaction shown below.

Suggest a four-step synthesis involving an organocuprate reagent to produce the desired product.

Determine the structure of the compounds corresponding to i-iv for each of the following reactions:

Show how you could accomplish the following conversion.

Write the synthesis of the below-given compound starting with a carboxylic acid as one of the starting materials.

Use an alcohol and an alkyl halide each as a starting material in two different methods to make ethyl benzoate.

Draw the product of the reaction given below.

Identify the missing products.

Provide any necessary reagents to show how the following synthesis can be accomplished.

Show how the following synthesis can be carried out:

• butanoic acid → butanal

Use any reagents necessary.

Show how you would accomplish the following conversion through acid chloride intermediate.

• Phenyl benzoate from benzoic acid and phenol

Show how the following conversions can be accomplished using amides as intermediates.
a. butyric acid → N,N-dimethylbutan-1-amine
b. piperidine → N-ethylpiperidine
c. cyclohexanecarboxylic acid → cyclohexanecarbonitrile