Winter 2003 C6A

1.

Part 1: you are required to carry out a series of tests on two organic compounds, B and C. You are to use the information from the tests and spectroscopic data to propose identities for B and C. Identification of two organic compounds You have two liquid organic compounds labelled B and C. Each contains one functional group and each may be prepared from the other in one synthetic step. Carry out the following tests, recording your observations and inferences in the spaces provided. In the inferences column record the functional group that may be suggested by your observations. (a) To 0.5 cm3 of liquid B add solid phosphorus pentachloride. Observations Inferences

(2)

(b)

Add 5 drops of liquid B to 2 cm2 of aqueous sodium carbonate. Observations Inferences

(2)

(c)

To 5 drops of liquid B add 5 cm3 of aqueous iodine. Add aqueous sodium hydroxide drop by drop, mixing well until the iodine colour is just discharged. Allow to stand. Observations Inferences

(3)

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Winter 2003 C6A

(d)

Prepare a water bath by adding approximately 150 cm3 of tap water to a 250 cm3 beaker and heating it gently until it is almost boiling. To 1 cm3 of liquid C contained in a boiling tube, add 5 cm3 of aqueous sodium hydroxide and warm gently in the water bath for approximately 3 minutes. Add 6 cm3 of dilute nitric acid followed by five drops of aqueous silver nitrate. The hot water bath will be used again in Part 4 Observations Inferences

(2)

(e)
100

The mass spectrum of liquid C is given below.

80
Relative intensity

60

40

20

0 25 50 75
m/e

100

125

150

175

Identify the molecular ion on the mass spectrum, by marking it M+, and give its m / e value. ....... Draw the structure of the ion that gives rise to the peak with m / e = 43.

From the results of the tests identify C by giving its name.

2

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Winter 2003 C6A

....... Identify one other species with its m / e value that supports your conclusion. .......
(4)

(f)

Suggest the identity of compound B. .......

(1) (Total 14 marks)

2.

Part 2: you are required to plan a procedure to determine the purity of one of these organic compounds. Planning The precipitation test described in Part 1 test (d) may be adapted to find the purity of liquid C when prepared from the other compound in Part 1. Describe an experiment that would provide information allowing the purity to be determined. Include in your answer details of: the apparatus; the procedure; how the experimental data would be used. Do not invent numbers to illustrate your plan. ......... ......... ......... ......... ......... ......... ......... ......... .........
(Total 8 marks)

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Winter 2003 C6A

3.

Part 3: you are required to carry out a series of tests on compound A in order to identify A. Identification of compound A You are provided with about 0.5 g of a salt labelled A. The compound contains one cation and one anion. Carry out the following tests on A, recording your observations and inferences in the spaces provided. (a) Describe the appearance of A. Observations Inferences

(2)

(b)

Add about half of the solid A to 10 cm3 of distilled water contained in a boiling tube. Stir until all or most of the solid has dissolved. Any undissolved solid will not interfere with subsequent tests. Use separate 2 cm3 portions of the solution for the tests (i), (ii), (iii) and (iv). (i) To 2 cm3 of the solution of A add 2 cm3 of aqueous sodium carbonate. Observations Inferences

(3)

(ii)

To 2 cm3 of the solution of A add 2 cm3 of dilute sulphuric acid and two pieces of granulated zinc. Warm the mixture gently. Observations Inferences

(4)

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Winter 2003 C6A

(iii)

To 2 cm3 of the solution of A add 2 cm3 of aqueous lead(II) nitrate. Observations Inferences

(3)

(iv)

To 2 cm3 of the solution of A add 2 cm3 of aqueous barium nitrate solution. Observations Inferences

(2)

(c)

Add a few crystals of solid A to 1 cm3 of methanol. Observation only required

(1)

(d)

Comment on the bonding in compound A in light of your observation in test (c). .......
(1) (Total 16 marks)

4.

Part 4: you are required to find the crystallisation temperature of a solution of an inorganic salt. Determination of crystallisation temperature You are provided with a labelled boiling tube containing compound X. Use a burette to add 9.00 cm3 of water to the solid, and then place a thermometer in the mixture. Place the boiling tube in the hot water bath used for Part 1 (d) and stir its contents, with the thermometer, until the solid has just dissolved.

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Winter 2003 C6A

Immediately the solid has dissolved, remove the tube from the water bath and carefully wipe all traces of water from the outside. Stir gently with the thermometer and note the temperature at which crystals begin to form. Record the temperature to 0.2 C and insert the value into Table 1. Replace the tube into the hot water bath and stir the contents until the crystals redissolve. Repeat the cooling procedure to obtain a second estimate of the crystallisation temperature. Record this also in Table 1. Calculate the mean crystallisation temperature, recording your value in the space below the table, and then answer the questions that follow. Table 1 1st crystallisation temperature reading, t1/C 2nd crystallisation temperature reading, t2/C

Mean temperature of crystallisation, t3 = .. C

(5)

The mean solubility of compound X is given on the graph below.

95 90
Solubility, s / g per 100 cm3

85 80 75 70 65 60 55 50

40 45 50 Crystallisation temperature, T /C From the plot obtain a value for the solubility of X at temperature t3 = .g/100 cm3
6

30

35

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Winter 2003 C6A

Hence determine the mass, in g, of X that the boiling tube contained originally.

(2)

Evaluation Record, in the spaces below, the smallest volume printed on the burette scale, and the smallest division of temperature on the thermometer. Burette ... Thermometer . Given that X was weighed to a precision of 0.01 g suggest which measurement: mass, volume or temperature contributes most to the uncertainty in the value of solubility of compound X. Justify your choice. ......... ......... ......... Suggest how the accuracy of either the thermometer or the burette could be checked. ......... ......... ......... .........
(5) (Total 12 marks)

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