1995final exam - .i— ' DURATION: 3 HOURS CARLETON...

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Unformatted text preview: .i— ' DURATION: 3 HOURS CARLETON UNIVERSITY STUDENT NAME: MID-TERM EXIIIIITIOI STUDENT # DECEMBER 1995 N0. of Students: 210 Department Name & Course Number: Chanistry 65.2203 Course lnstructor(s) P . H . Bui st Au-monlnu usuonmnn N0 INSTRUCTIONAL AIDS PERMITTED Students MUST count the number of pages in this examination question papet before beginning to write, and report any discrepancy immediately to a ptocton This quemion paper has 9- pages. This examination question pope: MAY NOT be taken from the examination room. ————_——-————-———___.____________________________________ ANSWER ALL QUESTIONS ON THE EXAMINATION PAPER IN THE SPACE PROVIDED. TOTAL MARKS FOR THIS EXAM = 75 Cheerinistry' 65. MIDTERM EXAMI 1995 P. 1311151: 1. a. f. h. 220A NATION “'1 " GIVE Sl-lOFlT ANSWERS TO THE FOILOWING QUESTIONS IN THE SPACE PROVIDED. (15 marks). Give the three hybridzation states of carbon commonly found in organic compounds. What is meant by the diagnostic region of an IR spectrum. Use electronegativityr arguments to explain why the sulfur atom of thioethers is more easily oxidized than the oxygen atom of others. Draw the structure of a typical carbocation, carbanion and carbon free radical. Explain what is meant by steric hindrance as it applies to 8N2 reactions. Assign the {R}- or (S)-configurafion to the chiral centre of the molecule shown. Bl’llk G F Define what is meant by an enantiomer. Give the Huckel definition of an aromatic compound. - Chemistry 65.22031 DECEMBER 1995 MIMERM P._Buist 1. (oom'd) i. Define HOMO and LUMO. i. Epoxides react with nucleophiles while ordinary-ethers are resistant to nucleophilic attack. Why? k. Define what is meant by an electmphile. I. What is a typical pKa value for a terminal alkyne. In. Which bass might one use to quantitatively deprotonate an alcohol. 0. Explain in your own words what is meant by a pKa mimic: a Bronsted acid. Chemistry 65 . 220A DECEMBER 1995 MDTERH P._H—. B11131: . 2. PHYSICAL PROPEnflES: (5 masks). a. Explain why the melting point of benzene is so much higher than that of n-hexane. b. Show why ether dissolves an appteciable amount of water while pentane does not. - c. ' Account for the fact that CH3$H is a gas at FLT. while CH30H boils £1165 °C. d. WhyisCGi4 not easilyoxidized while CH4 servesafuel. e. Why is t-butyl alcohol miscible with water in all proportions, while n-butanol is not? Chemistry, '65. 220A DECEMBER MDTERM 1995 P.I_=.L. Bni‘st 3. SHOW THE REAGEN'I‘S NECESSARY FOR EACH REACTION: (10 marks). Br AAA —--—I-- W \ \ s -——-I'* s=o / / ——-—I- Y \|(01 1. 3. I = -——...g... — = — 2. 4. 0 Q _“* 0 CH3— OH -———)-. CH3— Cl CH3— CH2] ~—-—j- CH3— CHZOCHg —--—h- 0 H0 H Chemistry '65 . 220A MIDTERM DECEMBER 1995 a P.H.. Buist A {How THE STARflNG MATERIAL WHICH WOULD LEAD TO THE PRODUCTS SHOWN: 10 marks). 1. BH3 2. H202 Y‘ 0'2 , FeCI3 0“ -—--I-- CI 0 MCPBA ‘ at0 2 equiv. / S\ Chemistry 65. 220A Imam-Em. DECEMBER 1995 3 PE. Buist 5. SHOW THE EXPECTED PRODUCT OF THE FOLLOWING REACTIONS: (10 matks). “N03 H2304 H . O 0 N 2 Brz /=\ ——---—h- 1. 03 —-—i-- 2. Zn H BrngeBra —..._’.. + H0 Bra 0 —* _ (show stereochemistry of product) hi3: M a + Chemistry l6'5 . 220A 8 DECEMBER MDTERM 1995 ‘ P .E; Buist' 6. Draw a mechanism for the follqwing reactions, showing all intermediates. Use oudy arms to shun I meflowofelectronsfromelectmn rich toeiectronpoorsites. Give resdnanoefonnswhere appropriate. {15 marks). a. Br I Bra, H20 .III‘H ——-—————_)... OH b.- OH CFO C. Chemistry 65.2203 9 7a? DECEMBE3,MIDTERM 1995 P.H. Buist 7a. A bicyclic alcohol. Compound A, Owl-I130. undergoes reaction with dilute H2804 at 25 °C to yield a nfixtwe of Mo alkenes. Owl-H's. The major antene product, B, gfves only cyclopentanone after ozone treatment followed by reduction with zinc in acetic acid. Formulate the reaclions involved and identity A and B. (4 marks). b. Thesexatiractantgivenofibylheoormnonhouseflyisasimplealkenenamedmusoaiure.Propdsea synthesis of muscalure starting from aoelylene and anyr alkyl halides. (3 marks). H H ' l.— s—n og—(cugfilcwwc‘é aceiylene- ‘ muscalure c. Assume that you have been given a sample of (S)-2-octanol. How would you prepare (FD-2— chlorooctane? How would you prepare (Ryz-octanol. (3 marks). 96' vwk ...
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1995final exam - .i— ' DURATION: 3 HOURS CARLETON...

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