CIE Nov 2017 v2 Paper 4 Q8

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(a) Compound A can be produced from a plant hormone. 18 OH HO PMT (i) Compound A shows optical and geometrical isomerism. On the structure of A above,draw a line through the bond(s) that give rise to geometrical isomerism, circle all chiral carbon atoms. [2] (ii) Give the names of four functional groups present in A.[2] (iii) A molecule of A has 17 carbon atoms. State the number of carbon atoms that are sp, sp2 and sp3 hybridised in A. sp carbons =sp2 carbons =sp3 carbons =[1] (iv) When A is reacted with an excess of hot, concentrated manganate(VII) ions, a mixture of three organic compounds is formed. X and Y and Z (C10H14O7) (C3H4O3) (C4H6O3) Suggest the structures of Y and Z. (C3H4O3) (C4H6O3) [2]UCLES 2017 9701/42/O/N/17<br /> 19 (b) A mixture of three different compounds, J, K and L, was analysed by thin layer chromatography using a polar stationary phase and a non-polar mobile phase. The three compounds all have similar molecular masses. The resulting chromatogram is shown. PMT solvent front mixture (i) Identify which spot corresponds to each compound. compound spot J CH3COCO2H K HO2CCO2H L CH3CH2COCH2CH3 [1] (ii) Explain your answers to (b)(i).[1] (iii) What is meant by the term Rf value?[1] [Total: 10]UCLES 2017 9701/42/O/N/17 [Turn over<br />

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