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Alkene (1) 1. 10.0 cm3 of a gaseous hydrocarbon, A, was exploded with 100.0 cm3 of oxygen (an excess). The total volume after explosion was 75.0cm3. When the resulting mixture is shaken with aqueous sodium hydroxide, there was a decrease in volume of 25.0cm3. [all volume measured in room conditions] (a) Explain why there was a decrease in volume when the mixture was shaken with aqueous sodium hydroxide. Illustrate your answer with a balanced equation. (b) Why was the hydrocarbon mixed with excess of oxygen before the reaction? (c) Determine the empirical formula of A. (d) Determine the molecular formula of A given its molar mass is 70.0 g / mol (e) Draw all possible structural isomers for A (f) Which of the isomer in (e) on vigorous oxidation yields butanal as the only organic product? Write a balanced equation for the reaction. 2. (a) State Markovnikovs rule (b) An alkene A (C4H8) reacts with bromine water at room conditions to produce a compound B. Dehydration of B by concentrated sulphuric acid produces two isomeric bromoalkenes C and D. Vigorous oxidation of C gives ethanoic acid with D give propanoic acid. Identify A, B, C and D.

3. The following scheme shows some reactions starting from propene

(a) Can propene exhibit geometrical isomerism? Explain your answer. (b) Propene can be obtained from petroleum fraction via the cracking process. Write a balanced equation to shoe how propene might be produced by the cracking of C12H26. (c) Identify compounds B,C and D. Write equations for the reactions taking place. (d) Propene can be polymerized to poly(propene). Draw a repeating unit of poly(propene).


4. (a) What do you understand by cis-trans isomerism? (b) 0.84g of a gaseous hydrocarbon X occupies a volume of 360.0 cm3. In a separate experiment, 0.84g of X reacts completely with 338cm3 of hydrogen. All volumes are measured at room conditions. X react bromine in tetrachloromethane to produce Y. When X is treated with cold dilute potassium manganate (VII), Z is formed. Both Y and Z has two chiral carbon is their structures. (i) Determine the molecular formula of X (ii) Determine the structures of X,Y and Z (c) X exhibits geometrical isomerism. Draw the structures of the two geometrical isomers.

5. Show how you would carry out the following conversions. (a) Propene to 1,2-propandiol (b) 1-bromopropane to 2-bromopropane

6. (a) Propene, C3H6, reacts with hydrogen bromide to produce two isomeric products (i) Draw the orbital overlap diagram for the C3H6 molecules (ii) Draw the structures of the two isomeric products. (iii) Which of the two is the major product. Explain why it is so? (b) Propene reacts with bromine water to produce a compound which is optically active. (i) What do you understand by the terms optical isomerism? (ii) Draw the structures of the two isomers (iii) In what way do the two isomers differ from one another?

7. Consider 2-metylpropene (a) Draw the structural formulae of the organic products formed when 2metylpropene are treated separately with (i) bromine water in tetrachloromethane (ii) cold dilute acidified potassium manganite (VII) (iii) hydrogen bromide in the present of hydrogen peroxide (iv) Oxonolysis (state the catalyst required)

(v) Steam in the present of concentrated sulphuric acid (b) Indicates * any chiral carbon in the compounds above 8. Suggest how you would differentiate between the following pairs of compounds. State the reagent and conditions used and the expected observation (a) Hexane and hexane (b) Cyclohexane and cyclohexene

9. When ethene is bubble through hydrogen iodide in tetrachloromethane, only one organic product is formed. But when ethene is bubbles through hydrogen iodide in aqueous sodium chloride, three different organic products are formed. However, if the mixture is boiled under reflux only one organic product remains. Explain the observations.

10. (a) Combustion of a hydrocarbon A produes 2.64g of carbon dioxide and 1.08g of water. One mole of A reacts with one mole of bromine to produce a compound with a relative molecular mass of 216.0. Determine the empirical formula and molecular formula of A. (b) A has three isomers, B, C and D. B and C reacts with bromine to produce the same product which is optically active. Oxidation of B and D by acidified potassium manganite (VII) releases carbon dioxide gas. Determine the structure of B, C and D

11. (a) State Markovnikovs rule. (b) Use Markovnikovs rule to predict the major products when 1methlycyclohexene reacts with the following reagents. (i) HBr (ii) Bromine water (iii) Steam in the presence of phosphoric acid as catalyst 12. (a) State Zaitsev Rule (b) Write all equation of dehydration of 2-butanol. (State the major product) (c) State all the condition the required for the following conversion (i) Ethanol to Ethene (ii) Ethene to ethanoic acid