1. Dodec-1-ene has the structure shown.

CH3(CH2)9CH = CH2 (a) Draw the structures of the organic molecules produced when dodec-1-ene reacts with each of the following.

(b) (i) What type of isomerism is shown by the organic products in (i), (ii) and (iv)? (ii) Draw structures to represent these isomers, choosing any one of these products. [3] (c) Dodec-2-ene shows another type of isomerism. Draw and label diagrams which show these two isomers. [2] 2. Crude oil is the principal source of hydrocarbons. The following are examples of such hydrocarbons.

(a) Give the structural formulae of the organic products in the following reactions. (i) The reaction of ethane with bromine in the presence of u.v. light. (ii) The polymerisation of propene. (iii) The oxidation of propene with cold, acidified potassium manganate(VII). (iv) The reaction of cyclohexene with hydrogen bromide. (v) The reaction of cyclohexene with hot acidified potassium manganate(VII). [5] (b) Write equations for the following reactions. (i) The complete combustion of ethane. (ii) The action of steam on propene in the presence of a catalyst. (iii) The reaction of cyclohexene with hydrogen in the presence of a catalyst. [3] (c) The process of cracking produces useful substances from oil. (i) Explain why cracking is useful. (ii) Suggest an equation for the cracking of C16H34 into at least three fragments. [3] (d) Draw structures for each of the following polymers showing two repeat units. (i) poly(ethene) (ii) pvc [poly(chloroethene)] [2] [Total : 13] 4 Some perfumes and scents of flowers and fruit contain compounds which are structural isomers. Two such examples are citronellol and geraniol.

(a) Confirm that citronellol and geraniol are isomers by calculating their molecular formula and their relative molecular mass, Mr. (i) Molecular formula (ii) Mr [2] (b) Name two functional groups present in both molecules. [3] Citronellol and geraniol also show stereo isomerism. (c) On the diagram of the structure of citronellol above, draw a circle around a chiral carbon atom. [1] (d) (i) Draw the other cis-trans isomer of geraniol. [In parts (d) and (f) use R to represent a part of the molecule.] (ii) Explain why geraniol has no optical isomers. [2] (e) State what you would expect to see if citronellol was reacted with aqueous bromine. [1] (f) Draw structures of the organic products when geraniol reacts with each of the following reagents. [2] 2(i) an excess of H+/Cr2O7 under reflux (ii) hydrogen bromide, HBr [Total : 11]