CIE Jun 2013 v3 Paper 2 Q5

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Examiners For Use 10 Compounds containing the allyl group, CH2=CHCH2, have pungent smells and are found in onions and garlic. Allyl alcohol, CH2=CHCH2OH, is a colourless liquid which is soluble in water. (a) Allyl alcohol behaves as a primary alcohol and as an alkene. Give the structural formula of the organic compound formed when allyl alcohol is reacted separately with each of the following reagents. (i) acidi ed potassium dichromate(VI), heating under re ux (ii) bromine in an inert organic solvent (iii) cold, dilute, acidi ed potassium manganate(VII) (iv) hot, concentrated, acidi ed potassium manganate(VII) [5] (b) Allyl alcohol undergoes the following reactions. (i) When reacted with concentrated HCl at 100 C, CH2=CHCH2Cl is formed. State as fully as you can what type of reaction this is.(ii) When reacted with MnO2 at room temperature, CH2=CHCHO is formed. What type of reaction is this?[2]UCLES 2013 9701/23/M/J/13<br /> Examiners For Use (c) Allyl alcohol can be converted into propanal in two steps. 11 CH2=CHCH2OH step I CH3CH2CH2OH step II CH3CH2CHO (i) What reagents and conditions would be used for each step? step I reagent(s)condition(s)step II reagent(s)condition(s)(ii) Allyl alcohol and propanal are isomers. What form of isomerism do they display?[5] (d) Allyl alcohol may also be converted into propanal by using a ruthenium(IV) catalyst in water. CH2=CHCH2OH ruthenium(IV) catalyst CH3CH2CHO Suggest what is unusual about this single step reaction.[1] [Total: 13]UCLES 2013 9701/23/M/J/13 [Turn over<br />

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