PSPM DK024 SESI 2019/2020 Lecturer’s Edition DK024 Chemistry 2 Labuan Matriculation College 151 3 (a) Arrange the following compounds in order of increasing solubility in water. Explain your answer. I CH3CH(OH)CH2CH2CH3 II CH3CH(OH)CH(OH)CH2CH3 III CH3CH(OH)CH2CH3 [4 marks] (b) 1-pentene undergoes hydration with acidified water to produce compound N and P with a molecular formula of C5H12O. i. Draw the structural formula of N and P. ii. Suggest a chemical test to differentiate 1-pentene from N. State the observation and write the chemical equation. [5 marks] (c) The reactions of 3-methyl-2-pentanol are shown in the scheme below. i. Draw the structural formule of R, S and U. ii. State Q and T. [5 marks]
PSPM DK024 SESI 2019/2020 Lecturer’s Edition DK024 Chemistry 2 Labuan Matriculation College 152 4 (a) A compound V is formed when 1-pentanol is oxidised by using pyridinium chlorochromate, PCC. i. Draw the structural formula of V and give its IUPAC name. ii. Draw three (3) structural isomers of V. [5 marks] (b) 2,3-dimethylpentanal reacts with various reagents as shown in the following reaction scheme. i. Draw the structural formula of AA and BB. ii. State CC. iii. Explain why 2,3-dimethylpentanal does not give a yellow precipitate with iodoform reagent. [4 marks] (c) Compounds DD, EE and FF are isomers with molecular formula C4H8O. All isomers do not react with sodium metal. i. Draw the structural formula of DD, EE and FF. ii. Compounds DD and EE give silver mirror with Tollens’ reagent, but not FF. Suggest a chemical test to differentiate FF from EE. State the observation and write the chemical equation involved. iii. Oxidation of DD and EE produces GG and HH respectively. Draw the structural formulae of GG and HH. [9 marks] END OF QUESTION PAPER KERTAS SOALAN TAMAT
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