9701_s11_qp_23
A paper of Chemistry, 9701
Questions:
5
Year:
2011
Paper:
2
Variant:
3

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Methanoic acid, HCO2H, was formerly known as formic acid because it is present in the sting of ants and the Latin name for ant is formica. It was first isolated in 1671 by John Ray who collected a large number of dead ants and extracted the acid from them by distillation. In this question, you should give all numerical answers to two significant figures. At room temperature, pure methanoic acid is a liquid which is completely soluble in water. When we are stung by a ‘typical’ ant a solution of methanoic acid, A, is injected into our skin. Solution A contains 50% by volume of pure methanoic acid. A ‘typical’ ant contains 7.5 × 10–6 dm3 of solution A. Calculate the volume, in cm3, of solution A in one ant. volume = cm3 Use your answer to to calculate the volume, in cm3, of pure methanoic acid in one ant. volume = cm3 Use your answer to to calculate how many ants would have to be distilled to produce 1 dm3 of pure methanoic acid. number = For Examiner’s Use When we are stung by an ant, the amount of solution A injected is 80% of the total amount of solution A present in one ant. The density of pure methanoic acid is 1.2 g cm–3. Calculate the volume, in cm3, of pure methanoic acid injected in one ant sting. volume = cm3 Use your answer to to calculate the mass of methanoic acid present in one ant sting. mass = g Bees also sting us by using methanoic acid. One simple treatment for ant or bee stings is to use sodium hydrogencarbonate, NaHCO3. Construct a balanced equation for the reaction between methanoic acid and sodium hydrogencarbonate. In a typical bee sting, the mass of methanoic acid injected is 5.4 × 10–3 g. Calculate the mass of NaHCO3 needed to neutralise one bee sting. mass = g
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For Examiner’s Use Fermentation of sugars by bacteria or moulds produces many different organic compounds. One compound present in fermented molasses is 2-ethyl-3-methylbutanoic acid which gives a distinctive aroma to rum. (CH3)2CHCH(C2H5)CO2H 2-ethyl-3-methylbutanoic acid What is the molecular formula of 2-ethyl-3-methylbutanoic acid? How many chiral carbon atoms are present in a molecule of 2-ethyl-3-methylbutanoic acid? If none write ‘none’. A sample of 2-ethyl-3-methylbutanoic acid may be prepared in a school or college laboratory by the oxidation of 2-ethyl-3-methylbutan-1-ol, (CH3)2CHCH(C2H5)CH2OH. State the reagentthat would be used for this oxidation. Describe what colour change would be seen. reagentcolour change from to This reaction is carried out by heating the reacting chemicals together. What could be the main organic impurity present in the sample of the acid? Explain your answer. State whether a distillation apparatus or a reflux apparatus should be used. Explain your answer. For Examiner’s Use A structural isomer of 2-ethyl-3-methylbutan-1-ol is 2-ethyl-3-methylbutan-2-ol, (CH3)2CHC(OH)(C2H5)CH3. What colour change would be seen if this were heated with the reagents you have given in ? Explain your answer as clearly as you can. An isomer of 2-ethyl-3-methylbutanoic acid which is an ethyl ester is a very strong smelling compound which is found in some wines. This ethyl ester contains a branched hydrocarbon chain and is chiral. Draw the displayed formula of this ethyl ester. Identify the chiral carbon atom with an asterisk (*).