QUESTIONSHEETS ORGANIC REACTION MECHANISMS I FREE RADICAL SUBSTITUTION I FREE RADICAL SUBSTITUTION II ELECTROPHILIC ADDITION TO SYMMETRICAL ALKENES

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1 CHEMISTRY QUESTIONSHEETS AS Level AS TOPIC 14 ORGANIC REACTION MECHANISMS I Questionsheet 1 Questionsheet 2 Questionsheet 3 Questionsheet 4 Questionsheet 5 Questionsheet 6 Questionsheet 7 Questionsheet 8 Questionsheet 9 Questionsheet 10 FREE RADICAL SUBSTITUTION I FREE RADICAL SUBSTITUTION II ELECTROPHILIC ADDITION TO SYMMETRICAL ALKENES ELECTROPHILIC ADDITION TO UNSYMMETRICAL ALKENES NUCLEOPHILIC SUBSTITUTION I NUCLEOPHILIC SUBSTITUTION II HALOALKANES: SUBSTITUTION VERSUS ELIMINATION ELIMINATION OF WATER FROM ALCOHOLS TEST QUESTION I TEST QUESTION II 14 marks 13 marks 15 marks 19 marks 15 marks 14 marks 15 marks 14 marks 15 marks 16 marks Authors Trevor Birt Donald E Caddy Andrew Jones Adrian Bond Editors John Brockington Stuart Barker John Brockington Kevin Frobisher Andy Shepherd Curriculum Press Licence Agreement: Paper copies of the A-Level Chemistry Questionsheets may be copied free of charge by teaching staff or students for use within their school, provided the Photocopy Masters have been purchased by their school. No part of these Questionsheets may be reproduced or transmitted, in any other form or by any other means, without the prior permission of the publisher. All rights are reserved. This license agreement is covered by the laws of England and Wales Curriculum Press March Curriculum P ress Curriculum Press Bank House 105 King Street Wellington Shropshire TF1 1NU

2 TOPIC 14 Questionsheet 1 FREE RADICAL SUBSTITUTION I This Questionsheet refers to a mixture of chlorine and a large excess of methane. a) What, if anything, would happen if the mixture were stored in the dark? What would you expect to happen if the mixture were exposed to sunlight? (iii) Write an equation to show the role of the sunlight in a). (iv) What type of bond breaking is involved in a) (iii)? (v) What type of particle is produced in a) (iii) and what is its essential feature? Type of particle... [1] Feature... [1] b) The particles produced in a) (iii) attack methane molecules to give chloromethane. Write equations for the two reactions which occur at the propagation stage of the chlorination of methane. c) What type of reaction takes place at the termination stage? [4] Write an equation for one such reaction. d) Smaller amounts of other organic chlorides are also produced in this reaction. Show, by means of two outline mechanistic equations, how dichloromethane can be formed. [1] TOTAL / 14

3 TOPIC 14 Questionsheet 2 FREE RADICAL SUBSTITUTION II In this Questionsheet you will need the following bond dissociation enthalpies (all in kj mol -1 ). C H 412; C Cl 338; Cl Cl 242; H Cl 431. Ethane and chlorine react together in the presence of ultraviolet light by free radical subsitution. a) Write an equation for the overall reaction. b) The initiation stage of this reaction could occur by Equation I or Equation II:. Cl 2 2Cl Equation I.. CH 2 + H Equation II Why, in practice, are free radicals formed according to Equation I? c) In the first reaction of the propagation stage, a chlorine free radical attacks a molecule of ethane to give another free radical and a molecule of product. There are two possibilities:.. Cl + CH 2 + HCl Equation III.. Cl + H + CH 2 Cl Equation IV Predict, by calculation, which of these equations is likely to be correct.... [4] d) Explain how your prediction in c) could be confirmed by analysis of the final product for trace substances.... [4] e) One of the by-products of the reaction was investigated by mass spectrometry and found to have a molecular ion peak with an m/z value of 246. What is the formula of this organic product? (Note Chlorine exists as a mixture of the isotopes 35 Cl and 37 Cl.) Write outline mechanistic equations for the propagation step that leads to the formation of the product with m/z value of 246. TOTAL / 13

4 TOPIC 14 Questionsheet 3 ELECTROPHILIC ADDITION TO SYMMETRICAL ALKENES a) Define the term electrophile and explain how alkenes undergo electrophilic addition. In your answer, name the type of reaction intermediate and describe any bond forming or bond breaking processes involved. Definition... Explanation [4] b) Outline the mechanism of the reaction between ethene and bromine and name the product. Mechanism Name of product... [1] c) Experiments show that alkenes do not undergo electrophilic addition with pure, dry bromine in PTFE (polytetrafluoroethene) apparatus. Explain why this is, and suggest why the reaction will occur under ordinary conditions. Reason for the lack of reaction... Reason for reaction under ordinary conditions... [4] TOTAL / 15

5 TOPIC 14 Questionsheet 4 ELECTROPHILIC ADDITION TO UNSYMMETRICAL ALKENES a) Explain why, in the addition of hydrogen bromide to but-2-ene, CH=CH, there is only one product. If but-1-ene, CH 2 =CHCH 2, is used in place of but-2-ene, two compounds are formed. Write the formulae of these two products. (iii) Which of the two compounds in a) is the major product and why? Major product... [1] Reason [3] b) Propene can be converted to an alcohol X of molecular formula C 3 H 8 O by a two-stage process which involves sulfuric acid. Write equations for the two stages and name the alcohol X. Equations [2] Name of X... [1] A small proportion of an isomeric alcohol Y is formed with X. Name Y and, by referring to the mechanism for the first stage of the conversion, account for the relative proportions of X and Y. Name of Y... [1] Mechanism for propene reacting with H 2 SO 4 [4] Reason for relative proportions of X and Y [3] TOTAL / 19

6 TOPIC 14 Questionsheet 5 NUCLEOPHILIC SUBSTITUTION I a) Explain what is meant by a nucleophilic substitution reaction. b) Nucleophilic substitution occurs when bromoethane reacts with aqueous sodium hydroxide. Write an equation for this reaction. What feature of the bromoethane molecule makes it susceptible to nucleophilic attack? (iii) Why can the hydroxide ion function as a nucleophile? (iv) Outline the mechanism for this reaction. [3] (v) What type of bond fission occurs during the reaction? (vi) What type of bond is formed during the reaction? c) The length of a carbon chain is increased when a haloalkane reacts with potassium cyanide. Write an equation for the reaction of bromoethane with ethanolic potassium cyanide. Name the product. (iii) Outline the mechanism of this reaction. [3] TOTAL / 15

7 TOPIC 14 Questionsheet 6 NUCLEOPHILIC SUBSTITUTION II a) Propylamine, CH 2 CH 2 NH 2, can be prepared by heating 1-bromopropane with excess ethanolic ammonia in a sealed tube at C. Outline the mechanism of this reaction. b) Propylamine, like ammonia, can behave as a nucleophile and take part in a further nucleophilic substitution reaction with 1-bromopropane. [4] What two features of the propylamine molecule enable it to behave as a nucleophile? Write an overall equation for the further reaction, and name the product. Equation... [1] Name... [1] c) Silver ethanoate, COO - Ag +, reacts with 1-bromobutane to give an ester. Write an overall equation for this reaction and name the ester. Equation... [1] Name of ester... [1] Outline the mechanism of this reaction. (iii) Although esters can be prepared more cheaply by reacting carboxylic acids with alcohols, the silver ethanoate method in sometimes preferred in research laboratories. Suggest a reason for this. [3] TOTAL / 14

8 TOPIC 14 Questionsheet 7 HALOALKANES : SUBSTITUTION VERSUS ELIMINATION The products of the reactions of 2-bromobutane with alkalis vary with the conditions used. a) When the conditions are aqueous: Name the organic product... [1] What type of reaction occurs?... [1] (iii) What is the role of the hydroxide ion?... [1] (iv) Outline the mechanism b) When the conditions are alcoholic, a mixture of two isomeric alkenes is formed. [3] Name these alkenes... [2] What type of reaction occurs?... [1] (iii) What is the role of the hydroxide ion?... [1] (iv) Explain why two isomeric alkenes are formed. Support your answer by outlining the reaction mechanisms. [5] TOTAL / 15

9 TOPIC 14 Questionsheet 8 ELIMINATION OF WATER FROM ALCOHOLS a) Butan-2-ol can be converted into but-2-ene in the presence of sulfuric acid. State the reaction conditions. Write mechanistic equations for the conversion. (iii) Use your mechanism to show why but-1-ene is also formed in this reaction. [6] [2] b) Sulfuric acid is not an ideal catalyst for this reaction. Explain why this is so, and suggest an improved way of carrying out the reaction. Explanation [2] Improved method... TOTAL / 14

10 TOPIC 14 Questionsheet 9 TEST QUESTION I Cyclohexanol, a useful solvent, can be prepared from cyclohexane by a two-stage synthesis: Cl OH Stage 1 Stage 2 a) For each stage, suggest a suitable reagent and conditions, state the type of reaction, and write mechanistic equations. Stage 1 Reagent and conditions... [2] Type of reaction... [1] Mechanistic equations Cyclohexane Chlorocyclohexane Cyclohexanol [4] Stage 2 Reagent and conditions... [2] Type of reaction... [1] Mechanistic equations ( attempt to show the reaction intermediate.) b) How could the reaction conditions for Stage 2 be changed so as to produce cyclohexene rather than cyclohexanol? What type of reaction would now occur? Change of conditions... [1] Type of reaction... [1] [3] TOTAL / 15

11 TOPIC 14 Questionsheet 10 TEST QUESTION II If an organic compound contains two functional groups, these can behave independently of each other. This Questionsheet concerns the chemistry of the difunctional compound 1-bromobut-2-ene, referred to as Compound X. CH=CH CH 2 Br Compound X a) The reaction of X with hydrogen bromide gives two products in approximately equal amounts. Give the formulae of these two products. By reference to the intermediates formed in the mechanism, explain why the two products are formed in approximately equal amounts.... [5] b) Compound X will also react with the reagents shown below. In each case write down the formula of the organic product (or products) and state the type of reaction mechanism. Potassium cyanide in aqueous ethanol Product... [1] Type of reaction... [1] Bromine solution in hexane Product... [1] Type of reaction... [1] (iii) Concentrated sulfuric acid Products... [2] Type of reaction... [1] (iv) Aqueous sodium hydroxide Product... [1] Type of reaction... [1] TOTAL / 16

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