CIE Nov 2016 v2 Paper 2 Q4 (with explained solutions) |

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CIE Nov 2016 v2 Paper 2 Q4

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In each section of this question the structural formula of an organic compound is shown. For each compound answer the questions about it. PMT (a) CH3CH2CHBrCH3 (i) Name this compound.[1] (ii) This compound shows stereoisomerism. Draw the two stereoisomers in the conventional way. (iii) Give the structures of three other structural isomers of C4H9Br. [2] [3] (b) (C2H5)3CBr (i) Name this compound.[1] (ii) (C2H5)3CBr reacts with aqueous OH. Complete the mechanism for this reaction including all necessary curly arrows, charges, partial charges and lone pairs. CH3CH2 CH3CH2C Br CH3CH2 (iii) What type of mechanism occurs in (ii)?[1]UCLES 2016 9701/22/O/N/16 [3]<br />
PMT (c) CH3CH2CH2CHBrCH3 (i) Give the reagents and conditions necessary for the conversion of this compound into a mixture of alkenes.[2] (ii) Give the name of the mechanism for the conversion in (i).[1] (iii) Draw the skeletal formulae of the three alkenes produced by the conversion in (i). [3] [Total: 17]UCLES 2016 9701/22/O/N/16 [Turn over<br />

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Page 6 Cambridge International AS/A LevelOctober/November 2016 Mark Scheme Syllabus 9701 Paper 22 Question 4(a)(i) 2bromobutane Answer 4(a)(ii) e.g. of mirror images CH3 CH3 C H Br CH Br CH2 CH3 e.g. of swapped groups CH2 CH3 CH3 C Br CH3 C H Br CH3 CH2 CH3 CH2 4(a)(iii) CH3CH2CH2CH2Br (CH3)2CHCH2Br (CH3)3CBr 4(b)(i) 3-bromo-3-ethylpentane 4(b)(ii) CH3 CH3 CH2 CH3 CH2 + C CH2Br CH3 CH3 CH2 CH3 CH2 C+ CH2 OH - M1 = dipole and curly arrow from bond to (or just beyond) Br M2 = correct carbocation M3 = OH with curly arrow from lone pair on O to C(+) 4(b)(iii) SN1 / nucleophilic substitutionUCLES 2016 Mark 1+1 1 1 1 1 1 1<br />
Page 7 Cambridge International AS/A LevelOctober/November 2016 Mark Scheme Syllabus 9701 Paper 22 Question 4(c)(i) Sodium / potassium hydroxide Ethanol / alcohol AND heat 4(c)(ii) elimination 4(c)(iii) Answer Mark 1 1 1 1 1 Total: 17UCLES 2016<br />

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