–2– M09/4/CHEMI/SP2/ENG/TZ2/XX

SECTION A

Answer all the questions in the spaces provided.

1. Aspirin, one of the most widely used drugs in the world, can be prepared according to
the equation given below.

OH OCOCH3
O O H+
+ + CH3COOH
C C
COOH H3C O CH3 COOH

salicylic acid ethanoic anhydride aspirin ethanoic acid

(a) State the names of the three organic functional groups in aspirin. [3]

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(b) A student reacted some salicylic acid with excess ethanoic anhydride. Impure solid
aspirin was obtained by filtering the reaction mixture. Pure aspirin was obtained by
recrystallization. The following table shows the data recorded by the student.

Mass of salicylic acid used 3.15 ± 0.02 g

Mass of pure aspirin obtained 2.50 ± 0.02 g

(i) Determine the amount, in mol, of salicylic acid, C6H4(OH)COOH, used. [2]

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(This question continues on the following page)

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(Question 1 continued)

(ii) Calculate the theoretical yield, in g, of aspirin, C6H4(OCOCH3)COOH. [2]

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(iii) Determine the percentage yield of pure aspirin. [1]

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(iv) State the number of significant figures associated with the mass of pure aspirin
obtained, and calculate the percentage uncertainty associated with this mass. [2]

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(v) Another student repeated the experiment and obtained an experimental yield
of 150 %. The teacher checked the calculations and found no errors. Comment on
the result. [1]

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SECTION A

1. (a) carboxylic acid / carboxyl;

ester;
Do not allow carbonyl / acid / ethanoate / formula(–COOH).

benzene ring / phenyl; [3]

(b) (i) Mr (C7 H 6 O3 ) 138.13;

§ 3.15 · 2
n ¨ ¸ 2.28 u 10 (mol); [2]
© 138.13 ¹
Award [2] for the correct final answer.

(ii) Mr (C9 H8O 4 ) 180.17;

m ( 180.17 u 2.28 u102 ) 4.11(g); [2]
Accept range 4.10–4.14
Award [2] for the correct final answer.

2.50
(iii) (percentage yield u100 ) 60.8 %; [1]
4.11
Accept 60–61%. Correct answer is ± 0.8%

(iv) 3;
0.02
(percentage uncertainty u100 ) 0.80 %; [2]
2.50
Allow 0.8%

(v) sample contaminated with ethanoic acid / aspirin not dry / impure sample;
Accept specific example of a systematic error.
Do not accept error in reading balance/weighing scale.
Do not accept yield greater than 100%.

(vi) hypothesis not valid/incorrect;

Accept any of the following for the second mark

C–O and C=O bond lengths will be different;
C2–O3 bond is longer than C8–O4 bond;
C8–O4 bond shorter than C2–O3 bond;
a CO single bond is longer than a CO double bond;
Accept C8–O4 is a double bond hence shorter.

(vii) Brønsted-Lowry definition of an acid

proton/H+/hydrogen ion donor;

Conjugate base of CH 3COOH