Q1. The following pairs of compounds can be distinguished by simple test tube reactions.

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1 Q1. The following pairs of compounds can be distinguished by simple test tube reactions. For each pair of compounds, give a reagent (or combination of reagents) that, when added separately to each compound, could be used to distinguish between them. State what is observed in each case. (a) Butan ol and methylpropan ol Reagent... Observation with butan ol Observation with methylpropan ol (b) Propane and propene Reagent... Observation with propane Observation with propene (c) Aqueous silver nitrate and aqueous sodium nitrate Reagent... Observation with aqueous silver nitrate Observation with aqueous sodium nitrate Page 1 of 14

2 (d) Aqueous magnesium chloride and aqueous barium chloride Reagent... Observation with aqueous magnesium chloride Observation with aqueous barium chloride (Total 1 marks) Q. Aldehydes can be prepared from acyl chlorides. State how an aldehyde could be tested to show whether it is contaminated with traces of unreacted acyl chloride. State what you would observe. Test Observation (Total marks) Page of 14

3 Q3. Certain chemical tests were performed on the pain-relief drug ibuprofen. The results of these tests are given in the table below. Test Aqueous sodium carbonate Bromine water Acidified potassium dichromate(vi) and heat Fehling s solution and heat Result Effervescence Remained orange Remained orange Remained blue Which one of the following functional groups do these results suggest that ibuprofen contains? A B C D (Total 1 mark) Q4. (a) Consider the following pair of isomers. (i) Name compound C.... (ii) Identify a reagent which could be used in a test-tube reaction to distinguish between C and D. In each case, state what you would observe. Reagent... Observation with C... Observation with D... (4) Page 3 of 14

4 (b) Consider the following pair of isomers. (i) Name compound E.... (ii) Identify a reagent which could be used in a test-tube reaction to distinguish between E and F. In each case, state what you would observe. Reagent... Observation with E... Observation with F... (4) (c) Draw the structure of the chain isomer of F which shows optical isomerism. (1) (Total 9 marks) Q5. Samples of 1-chloropropane and ethanoyl chloride can be distinguished by the addition of an aqueous solution of silver nitrate. State what you would observe with each sample. Observation with 1-chloropropane Observation with ethanoyl chloride (Total marks) Page 4 of 14

5 Q6. The following five isomers, P, Q, R, S and T, were investigated using test-tube reactions and also using n.m.r. spectroscopy. (a) A simple test-tube reaction can be used to distinguish between isomers P and S. Identify a reagent (or combination of reagents) you could use. State what you would observe when both isomers are tested separately with this reagent or combination of reagents. (b) A simple test-tube reaction can be used to distinguish between isomer Q and all the other isomers. Identify a reagent (or combination of reagents) you could use. State what you would observe when Q is tested with this reagent or combination of reagents. Page 5 of 14

6 (c) State which one of the isomers, P, Q, R, S and T, has the least number of peaks in its 1 H n.m.r. spectrum. Give the number of peaks for this isomer. (d) Write the molecular formula of the standard used in 13 C n.m.r. spectroscopy. Give two reasons why this compound is used. (e) Figure 1 and Figure show the 13 C n.m.r. spectra of two of the five isomers. Figure 1 Figure Page 6 of 14

7 The structures of the five isomers are repeated to help you answer this question. State which isomer produces the spectrum in Figure 1 and which isomer produces the spectrum in Figure. Explain your answer. You do not need to identify every peak in each spectrum. Use Table C on the Data Sheet to answer the question. (5) (f) U and V are other isomers of P, Q, R, S and T. The 1 H n.m.r. spectrum of U consists of two singlets. V is a cyclic alcohol that exists as optical isomers. Draw the structure of U and the structure of V. U V (Total 17 marks) Page 7 of 14

8 Q7. (a) Propanoic acid can be made from propan-1-ol by oxidation using acidified potassium dichromate(vi). Propanal is formed as an intermediate during this oxidation. (i) State the colour of the chromium species after the potassium dichromate(vi) has reacted. (1) (ii) Describe the experimental conditions and the practical method used to ensure that the acid is obtained in a high yield. Draw a diagram of the assembled apparatus you would use. Conditions... Apparatus (4) (iii) Describe the different experimental conditions necessary to produce propanal in high yield rather than propanoic acid. (b) Propan-1-ol is a volatile, flammable liquid. Give one safety precaution that should be used during the reaction to minimise this hazard. (1) Page 8 of 14

9 (c) A student followed the progress of the oxidation of propan-1-ol to propanoic acid by extracting the organic compounds from one sample of reaction mixture. (i) Give a chemical reagent which would enable the student to confirm the presence of propanal in the extracted compounds. State what you would observe when propanal reacts with this reagent. Reagent... Observation (ii) Give a chemical reagent that would enable the student to confirm the presence of propanoic acid in the extracted compounds. State what you would observe when propanoic acid reacts with this reagent. Reagent... Observation (d) Predict which one of the compounds, propan-1-ol, propanal and propanoic acid will have the highest boiling point. Explain your answer. Prediction... Explanation (Total 15 marks) Page 9 of 14

10 Q8. Some alcohols can be oxidised by an acidified solution of potassium dichromate(vl). Aldehydes can be oxidised by Tollens reagent or by Fehling s solution. An unknown pure liquid A contains only a single alcohol. Outline a simple procedure to allow you to determine whether A is a primary, a secondary or a tertiary alcohol (Total 3 marks) Q9. The carboxylic acid 3-methylbutanoic acid is used to make esters for perfumes. The following scheme shows some of the reactions in the manufacture of this carboxylic acid. (a) One of the steps in the mechanism for Reaction 1 involves the replacement of the functional group by bromine. (i) Use your knowledge of organic reaction mechanisms to complete the mechanism for this step by drawing two curly arrows on the following equation. Page 10 of 14

11 (ii) Deduce the name of the mechanism in part (i). Give the IUPAC name of (CH 3 ) CHCH Br (b) Reaction 3 is an acid-catalysed reaction in which water is used to break chemical bonds when the CN functional group is converted into the COOH functional group. Infrared spectroscopy can be used to distinguish between the compounds in this reaction. Deduce the name of the type of reaction that occurs in Reaction 3. Identify one bond in (CH 3 ) CHCH CN and a different bond in (CH 3 ) CHCH COOH that can be used with infrared spectroscopy to distinguish between each compound. For each of these bonds, give the range of wavenumbers at which the bond absorbs. Use Table A on the Data Sheet when answering this question. Page 11 of 14

12 (c) When 3-methylbutanoic acid reacts with ethanol in the presence of an acid catalyst, an equilibrium is established. The organic product is a pleasant-smelling ester. (CH 3 ) CHCH COOH + CH 3 CH OH (CH 3 ) CHCH COOCH CH 3 an ester + H O The carboxylic acid is very expensive and ethanol is inexpensive. In the manufacture of this ester, the mole ratio of carboxylic acid to ethanol used is 1 to 10 rather than 1 to 1. (i) Use Le Chatelier s principle to explain why a 1 to 10 mole ratio is used. In your explanation, you should not refer to cost. (Extra space)... (ii) Explain how a catalyst increases the rate of a reaction. (Extra space)... (Total 1 marks) Page 1 of 14

13 Q10. Ethanoic acid, propyl ethanoate and propan-1-ol are all colourless liquids. Esters do not give a positive result with any of the usual tests for functional groups. State how you could use chemical tests to show the presence of ethanoic acid and propan-1-ol in a mixture of the acid, the alcohol and the ester (Total 4 marks) Page 13 of 14

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A mass spectrometer can be used to distinguish between samples of butane and propanal. The table shows some precise relative atomic mass values.

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