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Clare's Girls' School Form 7 AL Chemistry Assignment 6 - Acid Derivatives & Amines
1. An amine, F, can be prepared by two different routes as shown :

(a) Write the systematic name for F. (b) Identify the compounds from A to F by giving their structural formulae. (c) Explain which one of the above routes is more suitable for preparing F. 2. Compound R and S are solids at room temperature with pKb values respectively equal to 4.2 and 5.8. It is known that they have the following structure :
O2N NH2 O2N NH2

(a) Identify, with explanations, which one of them is R. (b) Devise a procedure to separate R and S from a solid mixture of the two compounds. 3. (a) Compound A, a dibasic acid that occurs in apples and other fruit, has the following composition by mass : C, 35.8 %; H, 4.5 %; O, 59.7 %. A reacts with ethanol in the presence of concentrated sulphuric acid under reflux to give B, C8H14O5. Compound B evolves hydrogen gas when treated with sodium metal and reacts with acidified potassium dichromate(VI) to give compound C. Compound C produces an orange precipitate with 2,4-dinitrophenylhydrazine but has no reaction with Fehlings or Tollens reagent. Compound A, on the other hand, gives another dibasic acid, D upon warming with concentrated sulphuric acid. (Relative atomic masses : H, 1.01; C, 12.0; O, 16.0) (i) Deduce ONE possible structure for each of the compounds A, B and C. (ii) Write appropriate equation(s) to represent the above-mentioned chemical changes. (b) Each of the above two dibasic acids, A and D, exists in more than one isomer. (i) Draw their structure in such a way so that the difference between them can be shown unambiguously. Also indicate the type of isomerism involved. (ii) For EACH pair of isomers, explain which one possess a higher melting point. 4. Suggest how you would distinguish between EACH of the following pairs of compounds by (I) a chemical method, and (II) a spectroscopic method. (a) and (b) and

5.

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).