Topic: Hydrocarbons 1. Chloroethane is used as a starting material for the production of time-release capsules in pharmaceutical products.

One way of preparing Chloroethane is to react chlorine and ethane in the presence of ultraviolet light. Which statement is correct about the first stage of the mechanism of this reaction? A The Cl Cl bond is split homolytically. C The C H bond is split homolytically. B The Cl Cl bond is split heterolytically. D The C H bond is split heterolytically.

2. Chloroethene, CH2=CHCl, is the monomer of pvc. What are the CCC bond angles along the polymeric chain in pvc? A They are all 109 . C They are all 120 . B Half are 109 and half are 120 . D They are all 180 .

3. Oxidation of an alkene Y gives a diol; further oxidation gives a ketone. What could be Y? A CH3CH=C(CH3)2 B (CH3)2CHCH=CH2 C C6H5CH=CHC6H5 D (C6H5)2C=CHCH3

4. The compound hex-3-en-1-ol, P, has a strong leafy smell of newly cut grass and is used in perfumery. CH3CH2CH=CHCH2CH2OH P What is produced when P is treated with an excess of hot concentrated acidic KMnO4? A CH3CH2CH(OH)CH(OH)CH2CH2OH B CH3CH2CH=CHCH2CO2H C CH3CH2CHO and OCHCH2CH2OH D CH3CH2CO2H and HO2CCH2CO2H 5. The complete combustion of alkanes to produce carbon dioxide and water is an important exothermic reaction. Which line on the graph shows the relationship between the number of carbon atoms in the alkane and the number of moles of oxygen gas needed for complete combustion of the alkane?

5. Cyclohexa-1,4diene is treated with a solution of bromine in tetrachloromethane.

Which product is formed?

6. Hydrogen bromide reacts with ethene to form bromoethane. What is the best description of the organic intermediate in this reaction? A It contains carbon, hydrogen and bromine. B It has a negative charge. C It is an electrophile. D It is a free radical. 7. On strong heating a hydrocarbon produces ethene, propane and but-1-ene in the mole ratio 5 : 1 : 1. What is the molecular formula of the hydrocarbon? A C17H34 B C17H36 C C19H38 D C19H40 8. Which molecules would be present in the photochemical chlorination of methane? 1 hydrogen 2 hydrogen chloride 3 dichloromethane A. 1, 2 and 3 are correct B. 1 and 2 only are correct C. 2 and 3 only are correct D. 1 only is correct 9. Which compound could not be obtained from cracking a sample of nonane, CH3(CH2)7CH3?

A CH3CH=CHCH=CHCH2CH2CH2CH3 C CH3CH2CH2CH2CH2CH=CH2 10. What can behave as an electrophilic reagent? A Br2 B Na C NH3

B CH3CH2CH2CH2CH3 D (CH3CH2CH2)3CH D CN

11. How many different substitution products are possible, in principle, when a mixture of bromine and ethane is allowed to react? A3 B5 C7 D9

12. Which reaction occurs with saturated hydrocarbons? A catalytic hydrogenation B ready decolourisation of aqueous bromine C polymerization D thermal cracking

1. Alkanes such as methane, CH4, undergo few chemical reactions. Methane will, however, react with chlorine but not with iodine. Relevant standard enthalpy changes of formation for the reaction of methane with chlorine to form chloromethane, CH3Cl, are given below.

(a) (i) Use the data to calculate Hreaction for the formation of CH3Cl. CH4 + Cl 2 CH3Cl + HCl (ii) The corresponding reaction with iodine does not take place. Use bond energy data from the Data Booklet to calculate a theoretical value for Hreaction for the following equation. CH4 + I2 CH3I + HI (iii) Suggest why this reaction does not in fact occur. [5] (b) (i) By using equations, describe the mechanism of the reaction between chlorine and methane to form chloromethane, CH3Cl. Identify, by name, the separate steps of the overall reaction. (ii) What is the intermediate organic species in this reaction? [7] (c) The energy of activation for the formation of CH3Cl is 16 kJ mol1. Use this figure and your answer to (a) (i) to complete the reaction pathway diagram below showing the formation of CH3Cl from CH4 and Cl2. Show clearly the intermediate organic species and the final products. Indicate on your sketch the relevant enthalpy changes and their values. [4]

2. Octadecane, C18H38, is a long chain hydrocarbon which is present in crude oil. Such long chain hydrocarbons are cracked to produce alkanes and alkenes which have smaller molecules. (a) Give two different conditions under which long chain molecules may be cracked. [2]

(b) Octadecane, C18H38, can be cracked to form hexane and an alkene. Write a balanced equation for this reaction. [1] Alkenes are important industrially because the C=C bond makes them very reactive. (c) Ethene reacts with bromine to give 1,2-dibromoethane.

(i) What type of reaction is this? (ii) Outline the mechanism of this reaction, giving the structure of the intermediate. Show clearly any relevant dipoles, charges and lone pairs of electrons. 3. 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 an alkene and as a primary alcohol. Give the structural formula of the organic compound formed when allyl alcohol is (i) reacted with Br2, (ii) heated under reflux with an acidified solution of Cr2O72 ions.

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