Practice Questions (Organic Chemistry)
1(a) A and B have molecular formula C8H10. When A and B are treated with hot concentrated potassium manganate(VII), A forms C7H6O2 while B forms C8H6O4. B reacts with thionyl chloride, SOCl2 to form C and C reacts with methanol, CH3OH in the presence of a catalyst to form D, C10H10O4. Deduce the formula of A to D. [4] (b)(i) Draw the structural formulae of three alcohols with the molecular formula C5H12O. Label your structures E, F and G. [3] (ii) Label the chiral carbons on E to G with an asterisk on each carbon. [2] (iii) E, F and G are treated with an excess of acidified potassium dichromate(VI). E has no reaction with the reagent while F and G gave different products. Suggest simple chemical tests to identify the functional group on each of the products of F and G. Write chemical equations of all the reactions. [8] (iv) F is treated with PCl3 then with NaCN. After that, it is treated with LiAlH4 to give H. Draw the structural formula of H. [3] Answers : 1(a) A is C6H5...