samplefinal - CARLETON UNIVERSITY Saapfe FINAL “summon ,...

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Unformatted text preview: CARLETON UNIVERSITY Saapfe FINAL “summon , 1.996 200% w No. of Students: 175 Department Name a Course Number: Chemistry 65.220Ll/6/8’ Coureelnstructods) P.H. Buist nmnomm WM ' Students may be' issued extra paper for "rough notesf' Students MUST count the numbe: of pages in this examination question paper before beginning to write. and report any dimepancy immediath to a mentor. This question paper has 10 pages. This examination question paper MAY NOT be taken ftom the examination room Chemis try 65 . ZZOWySQmpU» Final Examination April 2M ’ 2 P.H. Buist 1. GIVE SHORT ANSWERS TO THE FOLLOWING QUESTIONS IN THE SPACE PROVIDED. (30 marks). Wit a. Define what is meant by a primary, secondaryand tertiary Aaleehei. b. Looking down the C2-C3 bond of CH3-CH2-CH2-CH3 , draw a Newman projection of the most favourable conformer. c. Use electronegativity arguments to explain why the pKa of H4N Cl is ca. 10 while that of HF is 3.2. d. Draw the structure of a typical phenol. e. Explain what is meant by resonance stabilization as it applies to the enoiate of acetone: "CH2€(=0)CH3. f. Assign the (R) — or (S)- configuration to the chiral centre of the molecule shown. HO 0.05? 9. Define what is meant by "nucleophilic substitution" with reference to organic compounds. A b. Give three examples of electrophilic reagents used in organic synthesis. Chemistry 6512091617 S’mfl... Final Examination April 1-9-95 200i] P.H. Buist 1. (cont'd) i What is me key physical measurement which one can use to distinguish a pair of enantiomers. j. (ydopropanes react with strong electrophiles while ordinary cycloalkanes are resistant to electrophilic attack. Why? k. Define what is meant by a Lewis acid. I. What is a typical pKa value for normal phenol. m. Why is ammonium ion a weaker acid than the conjugate acid of aniline? n. Define the 5 scale as it is used in the N.M.R. spectroscopy of organic moleCules. m05+ stable» 0. Draw methylcyclohexane in its chair conformation. Clearly label axial and equatorial hydrogens. A Chemistry 65.220335” 5%,.1. Final Examination April i996 2.00? P. H. Bui'st 2. PHYSiCAL PROPERTIES: (10 marks). 3. Explain why the boiling point of ethylamine (17 °C) is so much lower than that of ethyl alcohol (78 °C). b. Show how secondary amides .‘ (-NHC(=0)-) might hydrogen bond in an intermolecular fashion to stabilize the tertiary structure of proteins. c. Account for the fact that phenol is a solid at room temperature. d. Why is IR spectroscopy such a useful dagnostic tool in the study of carbonyl—containing compounds. e. Why is the melting point of cyclopropane (—128 °C) higher than that of the corresponding alkane - propane (— 188°C). Chemistry 65.220915}? Skhflfifia Final Examination April I996'zobf P.H. Buist 3. SHOW THE REAGENTS NECESSARY FOR EACH REACTION: (10 marks). H C 2, 0&0 (.3)le _—-—)- 0 O on 0 -——----—+ \A + 002 Y ——-——n- 0 E go” 1. O” —* ° 2. 1. Bot OEt HO fl —'""'—"’2 ‘n/\ +002 0 O ' O 3. O ANHJK + HCI /\NH2 ,_ Chemistry 65 . 220£I|LI 2 Final Examination April 1-9-96 P. H. Buist 4. SHOW THE STARTING MATERIAL WHICH WOULD LEAD TO THE PRODUCTS SHOWN: (1 0 marks). H30+ , heat 0 O H NH-NH2 NH—N H -——h— 2 equiv. I2 , OH' ” + I3C e o I. '0 at 2_ CH3CH2 -— c1 CH2CH3 I Et02C— CH- c023 H20 J H a H i D + NaBH4 O —+ OMe ' OH H0—< > 0 ——--a- Q + HCI o CHsMgBr OMgBr + CH30MgBr 2 equiv. No2 0‘ m- 0H SPWvI'ahefinS 02N N02 F'T Q ' 0H 0" in a? Chemistry 65.220'fl 5’ Final Examination pril 1-9‘9'6 9‘an P.H. BuiSt P 5. Show the expected product(s) of the following reactions (1 0 marks). " 0 HO! 0’5? G 0L..- l2 .. 0H d “ W HelPd D —" O _ BI ———-h- o 9 O O 1. [40 M —"'"_""""’ 2. EtBr 0 90H excess —>- I NME heat 0 C10 I. MCI/H ——>— 1. CH3], excess CNH ’ 2. AgOH, heat W LAIHV O CH3Li 0% —g/ ' cTMYUL-M + Ere Chemistry 65.220‘HH5’ 1 8 Final Examination April 1:996 2,65% P.H. Buist 6. Draw a mechanism for the following reactions, showing all intermediates. Use curly arrows to show the flow of electrons from electron rich to electron poor sites. Give resonance forms where appropriate. (10 marks). O O 0 JL CH30H JL 4, JL 1-] 0 H OH H OCH3 A Spontan eOUS \ I O H 0 l equiv. Bra 2' -:: Br CH3- 4m -CH3 ——-—,—-—-—> - H® O CH H H 3\ f Chemistry 65.220lriélz SAMLE’. I 9 1% Final. Examination April 1:996 2.0»? P. H. Buist 7. a) Iaé'tab. mohcwC-b, f4, “brag. 4" J’fierazjmm can/{716$ Mm; er‘chS 0H D'Huz 2 4,-l-ereoc‘3'amm 09E Inc/camis- 4.. maria) c) Dena/Lu: m Maw? {worm (Erma/L.) I) FQCQMQQ 2) CLAS'J'erCOnaeF 3) op‘iimfi 4'65 Vii? Chemistry 65.2204fléIY Final Examination April 1-996" 2019-1” P.H. Buist 8a. Oleamide, shown below, is a newly discovered sleep-inducing lipid whose structure has recently been confirmed. Give the expected, 6 value of the 1H NMR absorptions for the hydrogens situated at the positions indicated by the arrows. (3 marks). i H L" n L" ' “ cW/WNW J _ H + H R f O oleamide 8b. Sketch the 1H NMRsrarfraq-of ¢-CH2-C(=O)0CH3; [¢ = phenyl]. (3 Marks). ‘5 g /CH2—c-*oc;~53 (‘I‘Mfl For MOIQ"CulgSIAv—Di how may", [PICS (AW 0 8c. 7. r @“3 F“ A ' 5 10 g h}: curred 9» “H “(NMR Orcer :51, 'H-che ...
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This note was uploaded on 07/21/2010 for the course SCIENCE CHEM 2204 taught by Professor Buist during the Spring '10 term at Carleton.

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samplefinal - CARLETON UNIVERSITY Saapfe FINAL “summon ,...

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