9701_w06_qp_2
A paper of Chemistry, 9701
Questions:
5
Year:
2006
Paper:
2
Variant:
0

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For Examiner’s Use Lactic acid, 2-hydroxypropanoic acid, CH3CH(OH)CO2H, occurs in sour milk. Glycollic acid, 2-hydroxyethanoic acid, HOCH2CO2H, occurs in sugar cane. Lactic acid may be synthesised from propene by the following sequence. step I step II CH3CH=CH2 CH3CH(OH)CH2OH CH3CH(OH)CO2H What reagentand conditionare used for step I? reagentconditionWhat type of reaction is step II? Glycollic acid may be synthesised from ethanoic acid by the following sequence. step III step IV CH3CO2H ClCH2CO2H HOCH2CO2H Suggest the reagentand conditionthat are used for step III. reagentconditionWhat reagents and conditions are used in step IV? reagentcondition Lactic acid and glycollic acid react differently when heated under reflux with acidified dichromate(ions. Draw the structural formula of the organic product in each case. product from lactic acid product from glycollic acid For Examiner’s Use Lactic acid is chiral. Draw displayed formulae of the two optical isomers of lactic acid clearly showing their three-dimensional structures. Indicate with an asterisk (*) the chiral carbon atom in each. Glycollic acid and lactic acid each give the reactions of an alcohol group and of a carboxylic acid group. Each compound will react with the other to give an ester. When one molecule of glycollic acid reacts with one molecule of lactic acid, it is possible to form two different esters. Draw the structure of each of these esters. Glycollic acid and lactic acid are reacted together to make the material for ‘soluble stitches’ (also known as ‘soluble sutures’) which are used in surgery. In this material, many molecules of each acid have been reacted to form a long chain ‘polyester’ molecule which contains many ester groups. This polyester is used in surgery to sew up wounds inside the body. Over a period of time, the polyester undergoes a chemical reaction and breaks up to re-form the two individual hydroxy-acids. This reaction occurs where the pH of the body is about pH5 to pH6. Suggest what type of chemical reaction causes the polyester material to break up. Suggest why the products of this reaction are soluble in water.