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W08 final key - 1 Manashi Chattery'ee PhD A‘ 5 ‘.Q ¥ M...

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Unformatted text preview: ._ 1/ Manashi Chattery'ee PhD. A‘\ 5 ‘ .Q/ ¥ M J page -1 Winter 2008-Chem 30 A—Final KKK? \C/ Last First Name Name I Student ID Number : “ Name of your TA: . (Please Circle) Bree / Em Total: Discussion Section - Day : Time: / 200 Chem 30 A Winter 2008 Final (180 mins) Wednesday March 19, 2008 Electronegativity values for some atoms (Pauling scale) DO NOT OPEN THIS EXAM UNTIL INSTRUCTED TO DO SO Manashi Chatterjee Ph. D. page -2 Winter 2008-Chern 30 A-Final Manashi Chatterjee Ph. D. page -3 Winter 2008—Chem 3O A—Final 1. Penicillin V is a broad-spectrum antibiotic isolated from penicillium mold. Answer the questions below. (16 points) ( 1 i i' v N OW“ :0: Penicillin V H u ., ”N *.,4 """ CH3 . - Q, T MCQ® f—fi MOS 4‘: dud/C 2 Charge all”, {7° Br/F 3 a. [2 points] What is the hybridization state of atoms (labeled 1, 2, and 3) in the Penicillin V? (a) Xsp 2. sp2 3. spa (b) 1. sp3 2. sp 3, sp _ _ w _‘ c a b (c) 1. sp3 2. sp3 3. sp2 (d) /1(sp2 2. sp 3. sp2 P b. [2 points] How many chiral centers are present in Penicillin V? Answer is: L {1’9} 5 c. [2 points] Identify the chirality centers by * on the above structure. :2 vi‘) d. [2 points] How many lone pairs of electrons are present in Penicillin V? (1 *3 - "D . ‘ \ Answer is: l “i e. [4 points] Name all the functional groups present in Penicillin V? (use primary / secondary Where appropriate) gib- Q: Q mid" g». ,ama: pewtmt‘c odd f. [2 points] Identify the most acidic proton in Penicillin V (Circle the proton on the above . \ 5 structure)? ‘2? 5 qpb g. [2 points] Indicate one transformation that you will make to synthesize a new analog of penicillin V that is more acidic than the present molecule? Explain in less than 15 words. -—— g‘hnxag Goon m c.0531 _ ' QV‘CWQ; 0K‘—\\ \‘0 MW U2) alpfi Manashz' Chatterjee PhD. page -4 Winter 2008-Chem 30 A—Final 2. [2 points] Which structures belong to the ester class of molecules? OCOCH3 é CHZCOCHZNHZ II III IV (a) | and II (b) III onl c IV onl , ~ y ( ) y fl? 5 (d) | and IV 3. [6 points] What are the configurations for the stereocenters in the given molecules? Br CH / 2 I H \\\\OCH3 \c H CHZCH3 >‘\ H\\\\\\\\ \\CN HSHZC COOH COOH ‘ l CH3 geek; III ,i, I H 2 <3 4. [2 points] Which are meso compounds? EH2 / N 0” lg CHZOH H ; Cé Br CH3 CH 0 E I E I I I H j C\\ H3C _ H OCH3 NH2 \ N CH Br CHZOH 3 (a) I (b) ||,|I| (c) l||,lV (d) |,l|| Manashi Chatterjee PhD page -6 Winter 2008—Chem 30 A-Final 9. [8 points] Stereoisomers of 2—amino-3-hydroxybutanoic acid (Threonine) are shown below: QOOH c__:00H U H]: NH2 ”:3 NH2 HOOCINH2 HO 3 H H 5 OH HO 5 H EH3 6H3 CH3 I II III a) [2 points] What is the relationship between structure I and II: g i jg 533:” [fig I [)6ij OZ?) . . 2r: [ z: 2;“? b) [2 pomts] What is the relationship between structure II and III: ” ' ‘ 8F c) [4 points] Which structure represents the (2R,3R) isomer: . i i Ll [3b 10. [6 points] Draw 3 isomeric compounds (I; II; III) which when treated with HCl give the product in the reaction shown below? CI HCl ”30 I / II / Ill CH3 \ / I 11 III ea ( TLLC:\I\ Manashz' Chatterjee PhD. page —7 Winter 2008—Chem 30 A—Final 11. [3 points each] Give the major product of the following reactions. Show stereochemistry and all possible stereoisomers where appropriate. Write “No Reaction” where appropriate. H2 / Lindlars catalyst ———————> k MeOH solvent b) ('3‘ CH3'C ~ 0 Cl «4 CH3coo-Na+ ——-—————> DMF OH 0) CH3CH2CH20H + KI DMSO OH is not ‘1 LCM-’3 3W? +— d) Br NaOCHZCH3 J 2 ethanol H CH3 3 ' J Manashi Chatterjee Ph. D. page -8 Winter 2008-Chem 3O A-Final 6) 1. Hg(OAc)2, H20 2. NaBH4 f) (\me Base 2. CH3CH2Br (Amy/am" ) g) H (:0ch3 1. 0504 .__—____> 2. NaHSO3/ H20 Hacozc H Manashi Chattely'ee PhD. page —9 Winter 2008—Chem 30 A—Final 12. [8 points] What stereochemistry do you expect for the alkene obtained by E—2 elimination of (18, 28) —1,Z—dibromo—l,2—diphenylethane. Draw the sawhorse formula of (18,28) —1, 2-dibromo—1,2-diphenylethane (Box A) and the alkene product in Box B. Show proper arrows to demonstrate the E-2 elimination. Box A Box B l5.“ ‘5‘“ w KW NaOEt ' H H _ —> W 4:“ (9)039» EtOH (l S, ZS) -1, 2-dibromo-1,2-diphenylethane R l?) f) (twig?) 13. [6 points] Designate the following alkenes as E or Z. (Place the letter in the box). CIRCLE the highest priority groups on each of the sp2 carbons. _ ‘ a . Manashi Chatterjee Ph. D. page -10 Winter 2008-Chem 3O A-Final 14. [18 points] Give the major product of the following reactions. Please indicate stereochemistry where ever possible. \ H20, H2804, HgSO4 d H __ _.__.______> *5 ( hydrwh'on ) / 3? {erminai 3 “Haynes via. emfl methyl Lalo nc.s M‘ ) e la 'H CZHSO'Na+ ——————————> fl H ”mgr? ethanol 0 6015) Leaving 9"“? °" 2 Ear—x Br '- f q } no}. Cszo-Na ' 4n 1 H th l "/0” e 3110 BY CH3 Manashi Chatterjee PhD. page -1 1 Winter 2008—Chem 3O A-Final 15. [8 points] Provide a reasonable mechanism to account for the transformation (solvolysis) of A into B— show all steps including the properly drawn curved arrows and all intermediates. Make sure each individual step is mass— and charge—balanced. Br). H300 W CH3OH w ___—> heat Compound B Compound A Mamas/7i Chatterjee PhD. page -12 Winter 2008-Chem 3O A—Final 16.(a) [4 points] Write the product of the reaction of tosylate A with sodium azide in DMSO. Provide stereochemistry if applicable. Mechanism : Circle one SN1 E1 3N2, E2 16.(b) [4 points] Write the major product for the reaction of tosylate B with sodium methoxide in MeOH. Provide stereochemistry if applicable. OTs C Leaving 3m? 3 hydrogen“) C anH) Mechanism : 0 Circle one SNI E1 3N2 E‘2\_ Manashi Chatterjee PhD. page -13 Winter 2008—Chem 30 A-Final 17. [3 + 2 points] Norepinephrine is a biologically important molecule. (-)-Norephinephrine is the (R) isomer and has the required physiological property as a hormone and a neurotransmitter. Draw the 3-D structure of (-)-Norepinephrine. Hm) (—)—Norepinephrine Norepinephrine What can you say about the biological property of the S isomer? Explain in less than 15 words. fit (“out \r‘cwe 3&ch defied pmrbes bxpdmg *0 mm (remotes toot dtho‘t may 18. [4 points] Compound A is stable in ethanol (CH3CH20H), B is rapidly converted to another compound. Explain (less than 25 words) + H30 Q H30 Br r J 30 ...—-9 ‘ 4‘— Carbomhon 1° - CompoundA CompoundB 3° > 1° CCU ” ‘ -, E is (xitd‘bcx (Neon ‘rnbde and {‘3 ixfjeqylibk *0 ml chock ‘0“ mean [NWQ r Cmpcl A if‘jcx \Q cut/“b Mile 0nd Loch oo‘v Mercia SM quack 66 {as owe. \n W“. Mamas/11' Chatterjee PhD. page —14 Winter 2008-Chem 30 A—Final 19. [4 + 3 points] A hydrocarbon of unknown structure has the formula Cngo. On catalytic hydrogenation over Lindlar catalyst, 1 equivalent of H2 is absorbed. On hydrogenation over a Palladium catalyst, 3 equivalents of hydrogen are absorbed. a) How many degrees of unsaturation are present in the unknown? \ i ‘3 Answer is: a b) How many triple bonds are present? Answer is: \ \ ‘7‘ c) How many double bonds are present? Answer is: 3» l i d) How many rings are present? Answer is: i l e) Draw one structure that fits the data? 3 Pts \ \ H at“ \ d‘ /’/ \\ \\\i 20. [5 points] Give the absolute configuration of the stereocenters indicated by the arrow in the molecule called “Crixivan”. Crixivan (an HIV protease inhibitor) . . .. f \ 3‘ How many steremsomers are p0ssxble for Cr1x1van? . $2 Mamas/11' Chatterjee Ph‘D. Winter 2008-Chem 30 A—Final 21.. [10 points] (a) Propose a mechanism for the formation of Product A and Product B. CH2\\/ (‘7 4K HBI' + a) Br Br Product A Product B W\\e BF -~——> XL «L V 7 \_J ,, $35} page -15 1 Product B will have 52 stereoisomers. B b/ . .x - ‘ \ Which compond is the Maor Product and why? Q \l\ * Mamas/1i Chatterjee PhD. page -16 Winter 2008-Chem 30 A—Final 22. [10 points] Synthesize 3-bromohexane from acetylene (a two carbon alkyne) and appropriate alkyl halide (will require more than 1 step). Show stepwise synthesis and provide the reagents that you will use for the transformation. Br A/k/ Compound A Manashi Chatterjee PhD. page -17 Winter 2008-Chem 30 A-Final 23. [10 points] Predict the Ozonolysis products for the terpenes shown below. 2. (CH3)2s y»bisab01ene How many chiral centers are present in y—bisabolene? \ :3 \ P3“ How many Cis double bonds are present in y—bisabolene? -\» How many stereoisomers can y—bisabolene have? <1 \ (3* y—bisabolene is made up of 3 isoprene units. \ v‘h Circle the isoprene units in the terpene y—bisabolene Manashi Chatterjee Ph. D. page -18 Winter 2008—Chem 3O A-Final 24. [10 points] Synthesize 1-hexanol beginning from acetylene (two carbon alkyne; C2H2) and an appropriate alkyl halide. '# < EH @9102. Manashi Chatterjee PhD. page ~19 Winter 2008—Chem 30 A—Final 25. [8 points] Describe using Valence Bond Theory the orbitals used in bonding for Acetic acid [CH3COOH]. Show ground state C and O, excited state electronic configuration state for C and hybridization of atomic orbitals for C and 0 and their overlap using proper orbital diagram. Using VSEPR predict the bond angles and geometry (shape) around the 0C0 bond. \ _ '0 'Ph oco Bond angle: \ QC) Pr Hybridization of Carbonyl Carbon: Manashz' Chatterjee PhD. page -20 Winter 2008-Chem 30 A—Final 26. [3 points] Draw two resonance contributors of the aldehyde shown below. Show curved arrows to indicate movement of electrons. \\:>AY \ P3: ,. CUTC LCS 27. [3 points] Provide the correct order of the acidity of the following compounds in the box below: OCH3 OH COOH OH OH 1 2 3 4 strongest ’ weakest \ ...
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