Chemistry 9701 · AS & A Level · Carboxylic acids and derivatives

Carboxylic acids and derivatives — practice question

The structure of benzene-1,3-dicarboxylic acid appears below.
(a)[1]

State the empirical formula for benzene-1,3-dicarboxylic acid.

(b)[2]

Benzene-1,3-dicarboxylic acid is an isomer of benzene-1,4-dicarboxylic acid. These two isomers can be distinguished using carbon-13 ($^{13}\text{C}$) NMR spectroscopy. State the number of peaks in the carbon-13 ($^{13}\text{C}$) NMR spectrum of each compound.

(c(i))[1]

Name compound $P$.

(c(ii))[1]

Explain why the main product in this two-step synthesis is benzene-1,3-dicarboxylic acid rather than benzene-1,4-dicarboxylic acid.

(c)

Benzene-1,3-dicarboxylic acid can be made by the two-step synthesis shown below.

(c(iii))[1]

The reagents for step 1 are $\text{CH}_3\text{COCl}$ and $\text{AlCl}_3$. These reagents generate $\text{CH}_3\text{CO}^+$ ions, which then react with compound $P$. Name the mechanism of this reaction.

(c(iv))[3]

Draw the mechanism for the reaction of $\text{CH}_3\text{CO}^+$ ions with compound $P$. Include every relevant curly arrow and charge, the intermediate structure and the structure of compound $Q$.

(c(v))[1]

Suggest a reagent and conditions to convert compound $Q$ into benzene-1,3-dicarboxylic acid in step 2.

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