14.2. Alkenes
A subsection of Chemistry, 9701, through 14. Hydrocarbons
Listing 10 of 191 questions
By reference to the formation of σ and π bonds, describe and explain the shape of a benzene molecule, C6H6. 2,3-dimethylphenylamine can be prepared from 1,2-dimethylbenzene in two steps as shown. 1,2-dimethylbenzene CH3 CH3 M CH3 CH3 NO2 2,3-dimethylphenylamine CH3 CH3 NH2 HNO3 / H2SO4 step 1 step 2 Step1 is catalysed by H2SO4. Write an equation to show how H2SO4 generates the electrophile during step1. Draw the mechanism of the reaction between this electrophile and 1,2-dimethylbenzene to form M. Include all relevant curly arrows and charges. intermediate CH3 CH3 M CH3 CH3 NO2  Write an equation to show how the H2SO4 catalyst is reformed. For step2, suggest the reagents and conditions and name the type of reaction. ● reagents and conditions ● type of reaction  The drug mefenamic acid can be made using 2,3-dimethylphenylamine in an excess of 2‑chlorobenzoic acid. 2,3-dimethylphenylamine CH3 CH3 2-chlorobenzoic acid mefenamic acid CO2H CO2H Cl + + HCl NH2 CH3 CH3 N H Deduce the molecular formula of mefenamic acid. Name the functional groups, apart from the benzene ring, in mefenamic acid. 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.  mass of mefenamic acid = g The position of substitution in the electrophilic substitution of arenes can be explained based on the stability of the intermediate cations formed in the first step. The example given involves the bromination of methylbenzene. methylbenzene CH3 CH3 + CH3 3-position 2-position 4-position Br H Br H CH3 + + Br H Use this information and your knowledge about the stability of cations to suggest why the CH3 group directs incoming electrophiles to the 2- and 4-positions in preference to the 3-position. 
9701_s19_qp_42
THEORY
2019
Paper 4, Variant 2
Questions Discovered
191