CONFIDENTIAL UNIVERSITI KUALA LUMPUR Malaysian Institute Of Chemical & Bioengineering Technology FINAL EXAMINATION SEPTEMBER 2013 SESSION SUBJECT CODE : CLB 10803 SUBJECT TITLE : ANALYTICAL & ORGANIC CHEMISTRY LEVEL : BACHELOR ‘TIME / DURATION : 3HOURS INSTRUCTIONS TO CANDIDATES. 1. Please read CAREFULLY the instructions given in the question paper. 2. This question paper consists of two sections; Section A and Section B. 3. Answer ALL questions in Section A. For Section B, answer THREE (3) questions out of FOUR (4) questions. 4, Please write your answers on answer booklet provided. THERE ARE 7 PAGES OF QUESTIONS, EXCLUDING THIS PAGE,SEPTEMBER 2013 CONFIDENTIAL SECTION A (TOTAL: 40 marks) INSTRUCTION: Answer ALL questions. Please use the answer booklet provided. Question 4 (a) State the functional group for the following compounds, i Cand H only i R-OH il R-COOH iv R.NH2 v. R(C=O)R’ vi R-CHO (8 marks) (b) Figure 1 show the chemical structure of atenolol which is used to treat high biood pressure. Identify ALL the organic functional groups of atenclol OH Figure 1: Atenolol (marks) Compare the differences between aliphatic, alicylic and aromatic hydrocarbon with ONE (1) example each type of hydrocarbon. (S marks) (CLBID903 ANALYTICAL AND ORGANIC CHEMISTRYSEPTEMBER 2013 Question 2 (2) Name the following compound according to IUPAC nomenclature: cl HC CH,CH; H,C-CHs Hl CHs-C—C-C—CH, H | | “Ho He CH; HO—C—C—CHs | c HC-CH Hyco” ~~ CH3 Ho Ho Ho CHs CCC CHs CH,CH; (’) Draw the structural formula of each following: 3-(2-chloroethoxy)-1-butanol 2-ethyl-4,6-dimethylpheno| 2,2,3+trimethylheptane 2-methyl-1,3-butadiene 2-bromo-6-methyicyclohexanol (CLB10803 ANALYTICAL AND ORGANIC CHEMISTRY CONFIDENTIAL (5 marks) (S marks)SEPTEMBER 2013 CONFIDENTIAL (©) Draw the STRUCTURAL FORMULA and BONE LINE formula for each of the following compounds. cycloheptane 1,3-dimethyleyclopentane {-ethyl-2-methylcyclobutane propyleyclohexane cyclohexane (10 marks) SECTION B(TOTAL: 60 marks) INSTRUCTION: Answer only THREE (3) questions. Please use the answer booklet provided. Question 3 (2) Suggest FOUR (4) important reactions of alkynes (4 marks) {b) Creates the balanced chemical equation for each reaction from part 3 (a) by using 1- PENTYNE. (8 marks) (©) Justify each group of alkanes in order of increasing bolling point. i (CH,CH.CH.CH,CH, ii CH:CH.CH-CH, ii CHsCHCHs iv. CH:CH.CH.CH(CH:); v (CHs(CH.).CHs vi (CHs},CHCH(CHs)> (6 marks) (d) Explain the choice of order: (2 marks) ‘CLBID803 ANALYTICAL AND ORGANIC CHEMISTRYSEPTEMBER 2013 CONFIDENTIAL Question 4 (a) Identify the STRUCTURAL FORMULA and IUPAC NAME of the product by the following reaction i CHAC(CHs)=CHCH, + Br, SEK il, CH\CH=CHCH, + HCI Ch H,07 ii. CH3C(CH,)=CHCH; + HO —s Pt iv. Ho=CHs + Hp a v. CH;C(CH,)=CHCHs + O3 —ig (10 marks) (b) Compare the types of primary alcohol, secondary alcohol and tertiary alcohol with the GENERAL STRUCTURE and ONE (1) example each of each type. (6 marks) (c) Contrast between structural isomerism and stereoisomers. (4 marks) Question 5 (a) Identity the most widely used of instrument in analytical separation technique (1 mark) (b) ‘Support the answer in 5 (a). Give reasons why the above instruments is most widely used, (4 marks) (c) Explain FOUR (4) types of classification chromatography technique, (8 marks) (4) The analytical instrument in 5 (a) are comparable with gas chromatography (GC). Generates the similarity of both analytical instruments. (4 marks) e) Suggest THREE (3) suitable application analytical instrument in 5 (a). (CLBIO803 ANALYTICAL AND ORGANIC CHEMISTRYSEPTEMBER 2013 CONFIDENTIAL, (3 marks) Question 6 (@) Figure 2 shows the infra-red (|R) spectrum of 1-octene. Interpret ALL labels that it contains below. smote thot this bord 4s greater ‘han 3000 A Womens (er!) Figure 2:1-Octene (7 marks) (b) Outline the drawingof ALL the vibration mode involves iné (a) (4 marks) e (c) llustrate a diagram of basic component of IR and describe the process. (7 marks) (4) Summarize the absorption process of infia-red (2 marks) “END OF QUESTIONS PAPER” CLB10803 ANALYTICAL AND ORGANIC CHEMISTRYSEPTEMBER 2013 CONFIDENTIAL | oh i inl i APFENDINS Na) Kle és |e tela Mass 1 gl =0.003784 m* 1 gilmin= 631 x 10m'ls Pressure L pascal Pa) =1 Nx ‘Lam= 760 mnie =760 tor Latm= 101325 KPa (CLB10803 ANALYTICAL AND ORGANIC CHEMISTRY Force 1 Ibf=4 448008 IN=0224800W=1 kgm’? Density kgm = 0062428 bmSEPTEMBER 2013 CONFIDENTIAL Table 1.0 Characteristic Infrared Absorption frequencies ad Compound Type Frequency range, cat (290-2850) sack. 7970-13 0(y) scisonne and bendin= (3000-3020(a) sae 1OD-75G) bene [100-3000(R) sme (C=C fakes 1680-1640Gm.w) serch [e=c) PDO DTG 28) sets oe 1606, 1S00(@) sree co 136100005) / lo 1760-16706) stretch ~~ fMloncesaric — Aleabcls, Ponols fReio 160Gb) sve ]OH [Byeoges bonded — Alcohols Phenols [5600-3200 cvetch 000-2500) tetch (3300-3300¢en) sretch [1650-1500 (my bend f1340-1020¢m) serch {2260-2220¢%) seh Tee0-1500@) asymmemnca rec ‘y-Tanable, m -medium 5 ~srong, br -broed w - weak (CLB10903 ANALYTICAL AND ORGANIC CHEMISTRY