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CIE Jun 2015 v2 Paper 4 Q5
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![(a) Compound B is a component of several perfumes andavourings. It can be obtained by the hydrogenation of compound A. During the reaction, the hydrogen atoms all add onto the same side of the benzene ring. + 6[H] OH A OH (i) Suggest reagents and conditions for this reaction.[1] (ii) Circle all the chiral atoms on the structure of B above. [1] (iii) How many possible optical isomers are there with the same structural formula as B?[1] (iv) Complete the following part-structure to show the structure of one of the isomers of B that would be formed during the above reaction. (b) Compound A can be obtained from propan-2-ylbenzene by the following route. [1] step 1 step 2 propan-2-ylbenzene NO2 step 4 heat in water OH A NH2 step 3 (i) Suggest the structure of the intermediate cation C and draw it in the box above. [1]UCLES 2015 9701/42/M/J/15<br />
(ii) Suggest reagents and conditions for the following steps. step 1step 2step 3[4] (c) Suggest the structures of the organic products of the reactions between each of the compounds A and B and the following reagents. If no reaction occurs write no reaction in the relevant box. product with A, product with B, OH OH reagent HBr Na NaOH(aq)UCLES 2015 9701/42/M/J/15 [5] [Total: 14] [Turn over<br />](https://learnah.org/wp-content/uploads/2018/08/June_2015_v2_QP_-_Paper_4_CIE_Chemistry_A-level_5-0.jpg)
![Page 6 Cambridge International A LevelMay/June 2015 Mark Scheme o (a) (i) H2 + Pt or H2 + Ni / Pd + heat / warm or 50 < T < 500 (ii) o C (iv) 2 (iii) 2 = 4 OH CH(CH3)2 OH or CH(CH3)2 Syllabus Paper 9701 42 [1] [1] [1] [1] [1] [4] [5] 2 Hs have to be on the same side of the ring. Allow C3H7 or R for CH(CH3)2 OH (b) (i) or N2 or (ii) step 1: conc HNO3 + H2SO4 (@ 25 step 2: Sn / Fe + HCl step 3: HNO2 or NaNO2 + HCl (@ T< 10 Csee below) both temperatures correct for steps 1 + 3 (temperature not required for step 2) (inclusion of the word "heat" or "reflux" in step 3 negates the temperature mark) Csee below) ("aq" negates) C < T < 60 (c) HBr no reaction Br Na ONa ONa NaOH(aq) no reaction ONa [Total: 14]Cambridge International Examinations 2015<br />](https://learnah.org/wp-content/uploads/2018/08/June_2015_v2_MS_-_Paper_4_CIE_Chemistry_A-level_5.jpg)