CIE Nov 2017 v3 Paper 2 Q3

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Some reactions based on 1-bromobutane, CH3(CH2)3Br, are shown. CH3(CH2)3OH reaction 1 CH3(CH2)3Br reaction 2 CH3CH2CH=CH2 PMT reaction 5 reaction 3 CH3(CH2)2CHO CH3(CH2)3CN reaction 6 reaction 4 CH3(CH2)2COOH CH3(CH2)3COOH (a) For each of the reactions state the reagent(s), the particular conditions required, if any, and the type of reaction. For the type of reaction choose from the list. Each type may be used once, more than once or not at all. Each reaction may be described by more than one type. elimination hydrolysis substitution oxidation addition condensation reaction reagent(s) and conditions type(s) of reactionUCLES 2017 9701/23/O/N/17 [6] [Turn over<br /> (b) Complete the diagram to show the SN2 mechanism of reaction 1. R represents the CH3(CH2)2 group. Include all necessary charges, dipoles, lone pairs and curly arrows. PMT Br C O (c) 2-bromo-2-methylpropane is a tertiary halogenoalkane that is a structural isomer of 1-bromobutane. (i) Define the term structural isomer and name the three different types of structural isomerism. [2] definitiontypes of structural isomerism 123[4] (ii) 2-bromo-2-methylpropane is treated with the same reagents as in reaction 1. Methylpropan-2-ol is formed. Identify the mechanism for this reaction. Explain why this reaction proceeds via a different mechanism from that of reaction 1. mechanismexplanation[3]UCLES 2017 9701/23/O/N/17<br /> PMT (d) The product of reaction 2, but-1-ene, does not show stereoisomerism. However, but-1-ene reacts with HCl to form a mixture of structural isomers X and Y. but-1-ene + HCl X (exists as a pair of stereoisomers and is produced in higher yield than Y) Y (does not show stereoisomerism) (i) Explain the meaning of the term stereoisomers.[2] (ii) Give two reasons why but-1-ene does not show stereoisomerism.[2] (iii) Name X and Y. XY[2] (iv) Name the type of stereoisomerism shown by X.[1] (v) Use the conventional representation to draw the two stereoisomers of X. [2] [Total: 24]UCLES 2017 9701/23/O/N/17 [Turn over<br />

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