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Clare's Girls' School Form 7 AL Chemistry Assignment 5 - Acid Derivatives

1. Both propanal and propanoyl chloride react with methylamine, CH3NH2 , to give a product different from each other. (a) Write a mechanism for EACH of the two reactions. (b) Explain why the two reactions take a different pathway. 2. From the following facts and observation, deduce TWO possible structures for each of the organic compounds A, B and Z, and explain briefly your deductions. Also write appropriate equations to represent the chemical change. (a) A (C7H12O2) is an optically active ester. Upon hydrolysis, A gives a compound with a characteristic smell of vinegar. (b) B (C8H7ClO) forms white precipitate immediately upon mixing with aqueous silver nitrate. 3. Deduce ONE possible structure for each of the organic compounds M, N, P, Q, R, S and T. (a) An acyclic compound M of molecular formula C4H8O2 has a fruity smell. It does not produce a derivative with 2,4dinitrophenylhydrazine nor with propanoyl chloride. On reduction with excess LiAlH4, M gives only one product which reacts with ethanoic anhydride. [96-II 8a] (b) An acidic compound N (C4H4O4) on heating dehydrates to give compound P (C4H2O3). N gives compound Q upon hydrogenation. [95-II 7b] (c) An acyclic compound, R (C7H12O) can be converted to S and then to T :

Given that R exists as a mixture of geometrical isomers, S has a chiral carbon centre, and T does not have any chiral carbon centre. [00-II 7a] 4. A mixture of two organic products, G and H, was obtained in the reaction: [00-II 5d]

The mixture was separated by paper chromatography using a mixture of hexane and ether as solvent. The Rf values of G and H were found to be 0.84 and 0.55 respectively. (a) Deduce the structures of G and H. (b) Suggest a (i) chemical test and (ii) infra-red spectroscopy to distinguish between G and H. 5. Identify M, N, P, Q, R in the following reactions : 6. Using equations, indicate the reactions you would employ for the following conversions, which may involve more than one step. Give the reagent(s) for each step and the structure of any intermediate compound(s).

R (a polymer) END OF PAPER