1 drug is designed to simulate one of the following molecules that adsorbs onto the active site of an enzyme. Which molecule requires the design of an optically active drug? 2 Which one of the following is not a correct statement about vitamin, shown below? It is a cyclic ester. It can form a carboxylic acid on oxidation. It decolourises a solution of bromine in water. It is a planar molecule. 3 In which one of the following mixtures does a redox reaction occur? ethanal and Tollens reagent ethanoyl chloride and ethanol ethanal and hydrogen cyanide ethanoic acid and sodium hydroxide Page 1 of 13
4 Propanoic acid reacts with methanol in the presence of a small amount of concentrated sulphuric acid. The empirical formula of the ester formed is H 2 O 2 H 6 O 2 2 H 4 O 2 2 H 4 O 5 Which one of the following is not a correct general formula for the non-cyclic compounds listed? alcohols n H 2n+2 O aldehydes n H 2n+1 O esters n H 2n O 2 primary amines n H 2n+3 N 6 For this question refer to the reaction scheme below. Which one of the following statements is not correct? Reaction of W with sodium cyanide followed by hydrolysis of the resulting product gives propanoic acid. Mild oxidation of Z produces a compound that reacts with Tollens reagent, forming a silver mirror. Z reacts with ethanoic acid to produce the ester propyl ethanoate. W undergoes addition polymerisation to form poly(propene). Page 2 of 13
7 Ibuprofen is a drug used as an alternative to aspirin for the relief of pain, fever and inflammation. The structure of ibuprofen is shown below. Which one of the following statements is not correct? It has optical isomers. It liberates carbon dioxide with sodium carbonate solution. It undergoes esterification with ethanol. It undergoes oxidation with acidified potassium dichromate(vi). 8 utan-1-ol was converted into butyl propanoate by reaction with an excess of propanoic acid. In the reaction, 6.0 g of the alcohol gave 7.4 g of the ester. The percentage yield of ester was 57 70 75 81 9 Which one of the following would not react with aqueous silver nitrate to produce a precipitate that is soluble in concentrated aqueous ammonia? ar 2 [OI 4 ] 2 (H 3 ) 4 N + I H 3 Ol Page 3 of 13
10 Which compound is formed by the reaction of ethane-1,2-diol with an acid? H 3 H 2 O H 2 H 2 OH 11 Which one of the following types of reaction mechanism is not involved in the above sequence? H 3 H 2 H 3 (H 3 ) 2 Hl (H 3 ) 2 HN (H 3 ) 2 HH 2 NHOH 3 (H 3 ) 2 HH 2 NH 2 free-radical substitution nucleophilic substitution elimination nucleophilic addition-elimination Page 4 of 13
12 The compound lithium tetrahydridoaluminate(iii), LilH 4, is a useful reducing agent. It behaves in a similar fashion to NaH 4. arbonyl compounds and carboxylic acids are reduced to alcohols. However, LilH 4 also reduces water in a violent reaction so that it must be used in an organic solvent. Which one of the following can be reduced by LilH 4 to a primary alcohol? 13 n excess of methanol was mixed with 12 g of ethanoic acid and an acid catalyst. t equilibrium the mixture contained 8 g of methyl ethanoate. The percentage yield of ester present was 11 20 54 67 14 cid hydrolysis of produces H 3 H(OH)H 2 H 2 OOH H 2 (OH)H 2 H 2 H 2 OOH H 3 H(OH)H 2 H 2 OHO H 2 (OH)H 2 H 2 H 2 OHO Page 5 of 13
15 The structural formula of ethyl 2-methylpropanoate is 16 Hydrolysis of the ester, H 3 OOH 2 H 2 H 3, produces ethanoic acid. In an experiment, 2.04 g of the ester was used and 0.90 g of ethanoic acid was produced. The percentage yield of ethanoic acid was: 44 59 75 90 17 How many structural isomers, which are esters, have the molecular formula 4 H 8 O 2? 2 3 4 5 Page 6 of 13
18 H 2 O is the empirical formula of methanol methyl methanoate ethane-1,2-diol butanal 19 Summarised directions for recording responses to multiple completion questions (i), (ii) and (iii) only (i) and (iii) only (ii) and (iv) only (iv) alone Isomers of the ester HOOH 2 H 2 H 3, include (i) (ii) (iii) (iv) ethyl ethanoate methyl propanoate butanoic acid butyl methanoate 20 Ethanoyl chloride reacts with methylbenzene forming compound X according to the equation below. If the experimental yield is 40.0%, the mass in grams of X (M r = 134.0) formed from 18.4 g of methylbenzene (M r = 92.0) is 26.8 16.1 10.7 7.4 Page 7 of 13
21 In a reaction which gave a 27.0% yield, 5.00 g of methylbenzene were converted into the explosive 2,4,6-trinitromethylbenzene (TNT) (M r = 227.0). The mass of TNT formed was 1.35 g 3.33 g 3.65 g 12.34 g 22 This question is about the following reaction scheme which shows the preparation of polymer P. If 1.0 kg of benzene gave 0.98 kg of J, the percentage yield of J was 64 66 68 70 23 In which one of the following reactions is the role of the reagent stated correctly? Reaction Role of reagent TiO 2 + 2 + 2l 2 Til 4 + 2O TiO 2 is an oxidising agent HNO 3 + H 2 SO 4 H 2 NO + HSO HNO 3 is a rønsted-lowry acid H 3 Ol + ll 3 H 3 O + + ll ll 3 is a Lewis base 2O + 2NO 2O 2 + N 2 O is a reducing agent Page 8 of 13
24 The relative molecular mass (M r ) of benzene-1,4-dicarboxylic acid is 164 166 168 170 25 1,3-dinitrobenzene can be prepared by heating nitrobenzene with a mixture of fuming nitric acid and concentrated sulphuric acid. The reaction can be represented by the following equation. If the yield of the reaction is 55%, the mass of 1,3-dinitrobenzene produced from 12.30 g of nitrobenzene is 16.90 g 16.80 g 9.30 g 9.24 g 26 Which one of the following can react both by nucleophilic addition and by nucleophilic substitution? Page 9 of 13
27 Which one of the following does not contain any delocalised electrons? poly(propene) benzene graphite sodium 28 Which one of the following reactions does not involve donation of an electron pair? H + + H 3 NH 2 H 3 NH ll 3 + l 11 H 3 l + N H 3 N + l l 2 + I l + I 2 29 This question is about the following reaction scheme which shows the preparation of polymer P. Polymer P is formed in a two-step reaction from N. The first stage is a neutralisation reaction. The volume, in cm 3, of a 0.20 mol dm 3 solution of H 2 NH 2 H 2 NH 2 required to neutralise 6.8 10 3 mol of the acid N is 17 34 68 136 Page 10 of 13
30 Which compound can polymerise by reaction with itself? NH 2 H 2 H 2 NH 2 H 3 H 2 ONH 2 HOOH 2 OOH NH 2 H 2 Ol 31 Terylene is made by reacting benzene-1,4-dicarboxylic acid and ethane-1,2-diol. Terylene is an addition polymer. a polyamide. a polyester. a nylon. Page 11 of 13
Mark schemes 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 Page 12 of 13
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