OCR A Jan 2011 Paper 4 Q1

Answers available below

Answer all the questions. 1 Methylbenzene, C6H5CH3, is an aromatic hydrocarbon and is used widely as a solvent. It is readily nitrated and it can form mono-, di-, or tri-nitromethylbenzenes. (a) 4-Nitromethylbenzene can be formed by the nitration of methylbenzene. Outline the mechanism for the formation of 4-nitromethylbenzene from methylbenzene using NO2 + as the electrophile. (b) There are six possible structural isomers of CH3C6H3(NO2)2 that are dinitromethylbenzenes. Four of the isomers are shown below. Draw the structures of the other two isomers in the boxes provided. CH3 CH3 CH3 [4] NO2 NO2 isomer 1 CH3 NO2 NO2 isomer 4OCR 2011 O2N NO2 O2N NO2 isomer 2 isomer 3 isomer 5 isomer 6 [2]<br />
 (c) A research chemist investigated whether dinitromethylbenzenes could be used in the manufacture of fibres. The chemist devised a two-stage synthesis of the condensation polymer below, starting from one of the isomers in part (b). N H N H N H N H For the first stage of the synthesis,Which of the isomers 1, 2, 3 or 4 could be used? Identify the product formed and state suitable reagents.Write an equation. For the second stage of the synthesis, Suggest an organic compound that could react with the organic product from the first stage to form the polymer. State the type of condensation polymer formed.[6]OCR 2011 [Total: 12] Turn over<br />

Show answer