DKO24 CHEMISTRY SEMESTER 2 SESSION 2020/2021 2 HOURS CHEMISTRY UNIT (SES) KOLEJ MATRIKULASI MELAKA CHEMISTRY 2 HOURS REVISION SET 4 Do not open this question paper until you are told to do so INSTRUCTION TO CANDIDATE: 1 2 3 4 The question paper consists of one section only. Answer all questions. Answers must be written in the answer booklet provided. Maximum marks provided are shawn in brackets at the end of each question or section The use of an electronic calculator is permitted.Answer all questions 1 (@) Avolatile, sweet-smelling organic compound A contains carbon, hydrogen oxygen. Its empirical formula is CH,0» () The relative molecular mass of A is 74. What is the molecular formula for A (i) Write the general formula for A (iii) Draw two possible constitutional isomers for A having the same functional group. (iv) Draw another isomer of Awith a different functional group (6 marks) Identity the classes of the labelled carbon atoms in the following compound. tha nee 4 CH3CH3H =H (4 marks) Define the terms () Functional group (i) Homologous series (i) Isomer (3 marks) Redraw the following structure, then, circle and name all the homologous series. CHO (8 marks) 1|SES_KMM(2) Name the following alkanes according to IUPAC system () CH CHsGH-CHy CH-CH,CH, CH (ii) Gis OX (2 marks) (6) Cyclohexane reacts with bromine in the presence of sunlight to produce bromocyclohexane. () Name the type of reaction (i) Write the chemical equation (iii) Write the reaction mechanism for the formation of bromacyclohexane. (6 marks) (2) Based on the reaction scheme below, Bry CHCh mr, cHo0cH, B N CH3, HO.HO" c CH HN > Kano, OH cold E (i) Suggest the IUPAC name for the starting material (i) State the type of reaction that the starting material has undergone. i) Draw the structural formula for A, B, ©, D and E (v) State the rule used to determine the structure of 8. Explain your answer. (v) Suggest ane alcohol that can be used to synthesise the starting material. (10 marks) 2|SES_KMM(@) () Draw the structural formula for the follawing alkene. () — 1,2-diethylcyclobutene (i) trans-3,4-dimethyihex-3-ene (ii) S-chloropent-1-ene (iv) ois-2,3-dichlorabut-2-ene (4 marks) Classify the following alcohols. t fa i Or Of Ob " CH # 1-cyclohexylethanol 2-cyclohexylpropan-2-01 cyclonexylmethano! (3 marks) ‘Arrange the following compound in order of increasing bolling point. Explain your answer. octane; 1-heptanol (5 marks) When a person consumes alcohol, the alcohol gets into the blood by absorption through the stomach wall. Some self-test breath analyser kit estimate the amount of alcohol in the blood. When ethanol reacts with acidified potassium dichromate(V!) in the breath analyser, ethanol is oxidised to compound G and dichromate(V!) ian is reduced to chromium(It!) ion. () Draw the structure of compound G. (i) Ifalcohol is present, what is the change in the colour of the oxidising agent. (ii) What is the product formed if the oxidation of ethanol is incomplete. (3 marks) 3|SES_KMM(2) Name the following aldehydes and ketones by using the IUPAC system (i) QO (ii) CHO H. CH. ‘ots dl bs o fete, M taray eee aanenn H OHH H HOH CIH (4 marks) (©) An organic compound H, CzH,,0 forms a yellow precipitate when tested with 2.4-dinitrophenyhydrazine. H reduces Tollen’s reagent but H does not form any precipitate with alkaline iodine solution () Whats the functional group present in H? (i) Why does H give negative results with alkaline iodine? (ii) Draw the structural formula of H if it has quaternary carbon (iv) Give the IUPAC name for H (¥) Write a separate equation for the reaction of H with Tollen’s reagent and 2,4-dinitrophenyihydrazine (6 marks) (¢) Based on the reaction scheme below, D & = 5 Qo 9 NeCN. HCI i wa fy c= Noy, —Uoe Non we (Draw the structural formula for D and ¢ (i) State reagents A and 8 (4 marks) 4|SES_KMM.(2) Name the following compounds according to IUPAC nomenclature () coon No. (li), gooH NOs (2 marks) (©) Draw the structural formula of the following compounds. () — 4-methyi-4-pentenoic acid (i) 3-chloro-2-hydroxybutanoic acid (2 marks) (c) Compare the solubility of ethanoic acid and butanaic acid in water. Explain your answer. (5 marks) (4) Give name to the following reaction and write its equation Mixture of butanoic acid with potassium hydroxide solution. (3 marks) 5|SES_KMM