CIE Jun 2015 v2 Paper 4 Q6

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(a) Carboxylic acids can be converted into primary amines by the following sequence of reactions. 10 step 1 RCO2H step 2 RCONH2 step 3 RCH2NH2 (i) Suggest the identity of intermediate D and write its structure in the box above. [1] (ii) Suggest the reagents for step 1step 2step 3[2] (b) Four compounds, E, F, G and H, are isomers of each other. Each compound contains an aromatic ring and two functional groups from the following list.alcohol amide amine carboxylic acid ester phenol (i) Which of these functional groups react readily with cold HCl (aq)?[1] (ii) Which of these functional groups react readily with cold NaOH(aq)?[1] The molecular formula of the four isomers, E, F, G and H, is C8H9NO2. All four compounds are insoluble in water. Table 1 shows their solubilities in acid or alkali. compound solubility in HCl (aq) solubility in NaOH(aq) E F G H insoluble soluble insoluble soluble insoluble soluble soluble insoluble Table 1 9701/42/M/J/15UCLES 2015<br /> 11 (iii) Use this information to suggest the two functional groups, taken from the list on page 10, that each compound contains. compoundrst functional group second functional group (iv) Suggest a structure for each compound. [4] [4] [Total: 13]UCLES 2015 9701/42/M/J/15 [Turn over<br />

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