Test 4 - Chemistry of Arenes
Test 4 - Chemistry of Arenes
1 (a) By reference to the formation of σ and π bonds, describe and explain the shape of a benzene
(i) State the type of reaction mechanism that occurs in the reaction above. [1]
E [2]
(b) Cumene undergoes substitution reactions with chlorine to give several different isomeric
products with the formula C9H11Cl. The substitution can occur in the aromatic ring or in the
side-chain of cumene.
(i) Describe the conditions that are used to ensure substitution takes place only in the
(ii) Draw the structures of the two major isomeric products of the reaction, formula C 9H11Cl,
(iii) Describe the conditions that are used to ensure substitution takes place only in the
side-chain. [1]
(iv) Draw the structures of two isomeric products of the reaction, formula C 9H11Cl, when
(i) State the reagents and conditons for the reaction above. [2]
(ii) Write an equation to show the electrophile for the reaction is generated. [1]
(ii) Draw the mechanism of the reaction between this electrophile and 1,2-dimethylbenzene. Include
all relevant curly arrows and charges. [4]
(iii) When concentrated sulfuric acid is added to water, dissociation takes place in two stages.
(i) Write the expression for the acid dissociation constant Ka 2. [1]
(ii) H2SO4 is considered a strong acid whereas HSO 4– is considered a weak acid.
Suggest how the magnitude of the acid dissociation constant for stage 1 compares to Ka2. [1]
(e) Benzoic acid, C6H5CO2H, is a weak acid. A solution of 0.0250 mol dm –3 benzoic acid has a pH of
2.90. Calculate the Ka of benzoic acid. [2]
(e) The drug mefenamic acid can be made using 2,3-dimethylphenylamine in an excess of
2-chlorobenzoic acid.
(ii) Name the functional groups, apart from the benzene ring, in mefenamic acid. [1]
(iii) Calculate the maximum mass of mefenamic acid that could be formed from 5.00 g of
2,3-dimethylphenylamine in this reaction. Give your answer to three significant figures. [3]
(i) For this reaction name the type of reaction and identify the reagent and conditions needed. [2]