finalans - CARLETON UNIVERSITY £5 FINAL examination . 1936...

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Unformatted text preview: CARLETON UNIVERSITY £5 FINAL examination . 1936 2001+ Saar w No. of Students: 175 Department Name & Course Number. Chemistry 65.220'4/6/2’ Course lnstructofls) P.H. Buist AUTMOIIIIO “mum 'Students may be. issued extra paper for "rough notes," Students MUST count the number of pages in this examination question paper before beginning to Write. and repon any discrepancy immediately to a proetor. This question paper has 10 pages. This examination question paper MAY NOT be taken from the examination room. . ANIwEfl/I Nata: l) Iodo 1fan Readies». m M I Cave/real via day {w}- M flawed/“m 826%. 1) 'MC \‘FQWZZCYM H2 MCGAWmIf ‘ Metal Fern/Mien - IMM Formafic‘m bum-0‘5 React-a”. ‘ ' bf~£arowkmt§on , d—dech/aflon (den/{‘wtw epdwdf) _ {HooL (gene av maid. — iii/03511, % tad-6J3 ( 6a“ 0" Mad) - FLSGKu Cfiuifi‘caxdm rchfL'cfi Chemistry 65 . zzowjfiamph @ Final Examination April 199’s 2000‘ P.1-l. 1. Buist ANSLJEKS GIVE SHORT ANSWERS TO THE FOLLOWING QUESTIONS IN THE SPACE PROV1DED. (30 marks). gawk Define what is meant by a primary, secondary and tertiary aleehei. In is cw J, Par-me ) 1- latch/‘9 o/Ljawvfi' M10 - l 6' Jr 0 Mom on Mfiogen. K- Earth/2‘0, fi‘CIA/HKGEJ 2~chLGJ ,, Looking down the C2-C3 bond of CH3-CH2-CH2—CH3 , draw a Newman projection of me most favourable conformer. CH3 a i " H u I We H H . I n R, ’H . an:3 Use electronegativity arguments to explain why the pKa of H4N Cl is ca. 10 while that of HF is 3.2. .3; + e g N pg 1 NH3 H ® H c: T F 6‘ + H Draw the structure of a typical phenol. 0» Explain what is meant by resonance stabilization as it applies to the enolate of acetone: 3' 09 ' Maia-lire Maj-e mm .. H 2%CH2- 95m con/6m 4'0 oxygen‘ Assign the (R) - or (S)- configuration to the chiral centre of the molecule shown. 7 @ @J WW) are" 06 Define what is meant by "nucleophilic substitution" with reference to organic compounds. A a C9 m3? 39 group; Give three examples of electrophilic reagents used in organic synthesis. "' Br CH ~T “J? fgr I ) jJ-FS ‘3’" ) CHS'CTCQ Chemistry 65.220‘f/LIS’ Saucy... . ' 3 g Final Examination April 129-96 2007 P.H. Buist m. 511064 palm [oi C msz J n. Amman! 1. (cont'd) What is the key physical measurement which one can use to distinguish a pair of enantiomers. PolMt'mejfty -‘ mud/ems Jada/'50» Cyclopropanes react with strong electrophiles while ordinary cycloalkanes are resistant to electrophilic attack. Why? [yaw .9 [is Myanmm M W cm mica % (Lo/not 0t. paraffin. ' cad) Define what is meant by a Lewis acid. What is a typical pKa value for normal phenol. N10 Why is ammonium ion a weaker acid than the conjugate acid of aniline? » .. , 6-: 9 W3@ :9 2411-4 out Define the 6 scale as it is used in the N.M.R. spectroscopy of organic molecules. ‘ = m 0 Format: ‘ «Pajama m m”: may} ML: Draw methylcyclohexane in its chair conformation. Clearly label axial and equatorial hydrogens. A H cut: or Ha.“ H a p $7. a FL d7 C H l H 3 :_. 47/144.) 6 {1d a? 1 a? I? H? Chemistry 65 . 220qu“ 5%.ch _ 4 g Final Examination April .1996 2.00? P.H. BuiSt 2. pm It.) €ILJ PHYSICAL PROPERTIES: (1 0 marks). Explain why the boiling point of ethylamine (17 °C) is so much lower than that of ethyl alcohol (78 °C). - __ a _. _ . . r ""“2- march dipofie N—H A... CH3 ’ ‘h a Fwy my. 0—H C” ’9’“. N (690 e/Monvmm ‘3 6;. H 4*«q4 0. Show how secondary amides .' (-NHC(=0)-) might hydrogen bond in an intermolecular fashion to stabilize the tertiary structure of proteins. 0 flux MAKE l H o“ / rc/L ‘3'. Account for the fact that phenol is a solid at room temperature. @OM <2! H- Amadoy #5594114; PIW ‘ M) r5364, find/cable. Why is IR Spectroscopy such a useful cfiagnostic tool in the study of carbonyl—containing compounds. A 79f C50 WW Wye 15* Xufixt'flaw «effect; + fmt‘w M cm may»: Adm e-gfiqum pf M Jami/j Why is the melting point of cyclopropane (-128 °C) higher than that of the corresponding alkane - propane (- 188°C). Afls> 43G.me Chemistry 55.2mm»): 57am 5 a) Final Examination April 1 2,00" m1. Buist ANIMEIZJ 3. SHOW THE REAGENTS NECESSARY FOR EACH REACTION: (10marks). H 6 6) CH2, GK" “2'”? a“ a 0 OR A o J)- \/,|\ + 002 ® \n/ H 0 E h OH 1. Maj-l <:>=o o 0‘0 2. CH2¢ 9 13/ Q CH 1- 0 Ei’ 3 EOt OEt H0 ‘ W Ta? n; +002 WWYHrOé" 0 o ' 3 o . o a 3 H309 A o /\NH2__—"'*/{ce /\NHJ\ + “‘3' HQ 2 O-_-(—-————> WK +Hz6 mdctw' _ 0 H 0H o:.---——- 0Q 171091455731, Ali/w: via 0. 'H ' L90 __ 1.0151 ; M__a«rws + ebp’aMafiLaw We Mi muggy fl” WW5 Chemistry 55.220‘Iiu3 Eng? gfiginat ion April L996 2002‘; Us DE“; 6 £7 4. SHOW THE STARTING MATERIAL WHICH WOULD LEAD TO THE PRODUCTS SHOWN: (10 marks). [— OX H30" , heat hum L e, a?” we” C~ , ———>- O I J, 0 poncho H ’5: 0 @— NH- NH2 f N E Q 0‘:\H —"'2 equw @— NH-N H 4—— I2 , OH- I LOOOFO Mi T444- Voe + lac e (deck Tom) 0 0 (ho% in Mateo) L 3“ 5!- o C.“ _Co at 2.CH3CH2—-—Cl szZCH3 2 a 3’ Etozc— CH- COzEt O (3 .3 H207 H a . @0 kCH GO” + kc H 3 H 0 3 u NaBH4 0 W0!“ OMe ' 0 0H 02 H0 Q 0 WI, "—"' + HCI ‘9 o o CHaMQBr OMgBr V m_..__,. + CH30MgBr 0 CH 2 equiv. } No2 ‘3 "5" H10 ' 0H M36 w —* z. “’02, SWanems OzN N02 r—‘I - 0 ' ' 0H 0" 1H6 0‘? ——--—--_-—--I- Chemistry 65.22%] 3’ . Final Examination pril 1996' 1001’ S) P.H. Buist MngK5‘ 5. Show the expected product(s) of the following reactions (1 0 marks). H 0 Ho] Oj Ce 021/ /\H‘<°"‘ 6 ob I2 I IOH I o 4 g 6 “a?th .7???) 9! ‘K/ H2/Pd " _ H o O 9 0 a Cl ., CE I. N CL A 1. CH3I, excess 6 om @- - ~— + 2. AgOH,heat “ . M . i LafiHH - '4 \«o —. v’m 9% , ‘CH3Li 0_/ o I OTKVULM G) 0 Chemistry 65.2204198’ 3 2 Final Examination April 1:99-6- Zdb _ m1. Buist ‘f HMSwEIZS 6. Draw a mechanism for the following reactions, showing ail intermediates. Use curly arrows to show the flow of electrons from electron rich to eiectron poor sites. Give resonance forms where appropriate. (1 0 marks). til/£614 j: + i H 0 t H OH \H spon aneous A?! 0*“ x 06’ .4 ‘0” " (27 w 0 kg”; 9:004 —L i” 90 /" H d / H > 0 a F“ (i H20 , OH c4363“)?! H H H OH 57‘ ’” o ' 014 H10 Q OK OH WM X” “sf-'1 @014 + A3 (L) H6 ., (’7. K I . equiv. Bra . B CH3-Cd—fi- CH3 '—Hé————F~ .0 CH3 U- Ha i”? .“ofi h § @014 at?! C) l H CH... 10H A CH»C§ ’04 A ,_ 043/ ten 3 V- 3 C 3 «t CH; Cxw, [ u H (9“ Er H Chemistry 65.220‘f/5I2 SMMLE ‘ 9 ’3 Final Examination April 1996 209‘! ' P. H. Buist ANJLJEIQ‘ 7. a) * jihad; MOICCWLP’; _ CIM’JB WWW,- 0mg: 5 may army» 3;; MM . r O OH Mesa .f. Eggfle’ym‘z M _ ' at M £3 M'rrwffimc. QDRW "Hm, OHM?! 3 ¢¢¢r¢o£§0mm 47C mow—“wel- 4. (37nd.er hem (Kira/Q CH3 c.) Denim Hu. atoflawfi 4am momma) O racemqi'e : 50-56 Mfihre ofenmm ‘2.) Mf+ef80m~ef 5 Q Siefulé‘emm “M6244 ‘ Wfima‘f’ mrm 3) aficafi Mai/:3 _ _ , 65 Man/15mm ‘ Chemistry 65.220475 Y 10 Final Examination April 1996— 200% 3 P.H. Buist BIZ! 8a. Oleamide, shown below, is a newly discovered sleep-inducing lipid whose structure has recently been confirmed. Give the expec 17.2.4, 8 value of the 1H NMR absorptions for the hydrogens situated at the positions indicated by the arrows. (3 marks). a. w a. Vast-5:21.362 c J H +H ,H+3 0 L2 {,5 oleamide (~t ) 8b. Sketch the 1H NMRsfad'rm-of o-CHz-C(=O)0CH3; [(1) = phenyi]. (3 Marks). 0 (q, flaws.) For mole (ulgSIA-‘hD I lam-J Mama {9le “MAJ-d chi (rt-Fed c. - _ - w “k 'YNHR metric/um 01. ‘ 'H-IcSe Cowm‘: r . i é’H H?- )7 3 519k - 1‘ 2/9642!“ A B 8 ...
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finalans - CARLETON UNIVERSITY £5 FINAL examination . 1936...

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