118BWin10FinKey - 1. Reactions: (24 pts). Draw the...

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Unformatted text preview: 1. Reactions: (24 pts). Draw the structure of the expected organic product(s) formed in the following reactions including correct stereochemistry. If the product is racemic write both isomers or write racemic. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reaction”. 0H OSO,H20,HO ‘ " ' A) M __...__..4 22 5/\ WM OH \ C (C H3)3COK hv (w + W C) “i W ¢I D) 1) Brz (19(3), NH2 CF03, H2304, H2O o E) fl CF3COOOH __ 0\¢0 _______, I2 F) J% “W dY" 3 o I c) 2. Reactions: (24 pts). Draw the structure of the expected organic product(s) formed in the following reactions including correct stereochemistry. If the product is racemic write both isomers or write racemic. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reaction’. "u 3‘ Br2, CH3OH “ CH3 G) I M [I], TOLCQMIC Na, NH3 I/K/ ¢ /\ H) l) / H3O CN heat. : 5’ C” 1 ’ “vi + I ——_-> I + L “II \ a E A OHC CH 3 CHO _ ._ CH0 3 (bow WCQWMQ J) 1) CH3CI (3 eq), Aims \L‘ / 2) HI I 1" H 0 K) é 1) HSCHchzSH, ZnCI2 ————‘—> 2) Raney Ni, H2 0 L) O 1) ((CH3)2CHCH2)ZCuLi (“j 2) H30+ CH} ‘04ch 0‘3 3. Reactions: (24 pts). Draw the structure of the expected organic product(s) formed in the following reactions including correct stereochemistry. If the product is racemic write both isomers or write racemic. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reaction’. Br _ . M) Na+ M \N: O i 1) H9804, H20, H2804 ______.___. t4 2) NaBH4, CH3CH2OH 0) \/H/\ HEW”) ‘ /\ 0°C Br N) o O N CH L P) \JKH H:at N H CH3 Q) 1)(CH3)ZCHCOCI(1eq),AlCl3(xs) : l y 2) HSCD+ O O R) (b /\:0 H20, NaOH 4. Mechanisms: (30 pts). Show the detailed reaction mechanism for each of the following reactions. Include the structure of the expected products and all relevant resonance structures. 0A CH30H20H NF 4. ,_0+ @1507 0 CV A) /\/U\ H2304 H H OH O/R'rfiso‘l C90; ‘ /\/o}\ M l —’ ‘9 o MK g: M. + <— 0 0H K) H wq- 0‘ H V A. H5076 4 “15"! (“a «sol, 4‘ J ’ H 69041955 0 may“: i H am c" 00.5943 OCHLC 3 H 2. 3 H “emf”; Ottfid‘!’ fiSOLF “7.0 ' ,H 0 + H5011 L 0 Ha”! I/ G) l H 069/}, {iv/:50 :2 \O'NQ e “Ito—iml — -N l] “I \09 \0- U “50': H H 5. Synthesis: (21 pts). Show how you would carry out the following synthesis. Include the reagents you would need for each step and the intermediate products formed in each step. H l / /W\/0H ——-———» o Lawns. H2 vac, Clad; a ‘ C)/’/\G z) “30* / MN— Ml/H M I/ 0 /—-\ so AQLBA- r l ‘HO OH, H?— l’ r ’2)CH3cH’LMB o H / W /\/V>< ¢ "1 6. Vocabulary: (27 pts.) Fill in the blanks with the appropriate vocabulary word. If two words are iyen circle the correct one. A) Under K 'mgi] g control of a reaction most stable intermediate is utilized. This usually occurs at high I‘low lemperatures. B) Reactions generally proceed@ slower in an allyl system. C) The {if elimination uses an unhindered base to give a less I ® substituted alkene from an alkyl halide. D) Generally the (xi-carbon of a carbonyl acts as a go nucleophil / electrophile While the carbon in the carbonyl itself acts as a good nucleophile / electrophile. E) Hemicetals can be formed fiom carbonyls using base / acid neither as a catalyst, they are always@ never difficult to isolate as pure compounds. F) Hydroboration of an alkenc proceeds with an‘h " Mar-kwmuav regioselectivity and a@ anti addition of the new atoms. G) Halogen substituents in electrophilic aromatic substition donate electrons by T'Cscmante. but accept electrons by in J W ’50 h and generally give fast / slow ubstitution with 0"an & fk direction. H) In the electrocyclic opening of 3,4—dimethylcyclobutene with heat, the reaction proceeds in a CO” ralth direction. I) In general the dienophile of a Diels-Alder reaction is electron @and the diene @ electron poor. J) True IA benzene generally reacts under the same conditions as an alkene. K) True @etones are better electrophiles than aldehydes in aldol reactions. L) In general less substituted alkene is more ble than a more substituted alkene and is considered to be electron rich / (1 will react faster / slower with mCPBA than a more substituted alkene. Alcohols ldehydes / ketones / alkenes generally have the highest boiling point for their size. a: mi M1 . N) In 1H NMR of alkenes 6mm 5 coupling are the largest, $MI mi. couplings are small couplings that occur between hydrogens on the same carbon, and couplings are small couplings that cross four bonds. CN CHZSH CH H2NH20/%/CH3 H0H2c3)\(CI~'ZCH§H3 H/Kl/H \ CH20H3 E 2 E Z- 8. Identification: (6 pts). Label each of the given molecules as aromatic, nonaromatic, or antiaromatic. 6Q Arom. antlr non N\ o N .CLQL no“ Qfom. 9. Identification: (8 pts). Rank the following by pKa of the explicit hydrogen. 1 = most acidic and 8 = least acidic. 0 /\/\OH /U\H/ YNHg fiOH __7-.'__ 3 5 1 H H k V /K/ /\/H $ 10. Nomenclature: (15 pts.). Give the proper (IUPAC) chemical name or draw the structure of each of the following compounds. \ B.- J A) \W .. 5E,7Z—4—bromodec-5,7-diene-1 —yn-3-ol OH OH Li'lwpmwlpma‘ B) P’iSOPTOW‘ {$4an ‘1' U—me‘lkjle’thfl) benztnol C) \ Ci r // l° E;“In-(Altmgm'sibdiWEWO‘eC'Z'Cfl-s‘j , ’1. q ‘ 7 6 Q 3 C! CH ‘ 2 \ L‘- l 34‘ 0"" -2-kexunone D) 3 q 5" 3 "CYCO VA]. y V O O E) fie, 2 , LI, L-bnlmd'kflchoh {aha cow‘cm'dc L171 IQ. Spectroscopy: (34 pts.) The unknown compound A (C15H1302) gives the following proton and carbon NMR spectra Significant IR peaks were also observed. Compound B forms after reacting compound A with an excess of H2 gas and Pd/C. 3 H What are compounds A and B? 2H 1“ 8 7 6 5 4 3 2 1 200 150 100 so 0 IR: v 3327 (broad), 3050, 2950, 1530, 1590, 1209, 809 cm}. I UK»: 27‘0-43: W , HA=1HJ=9Hz(d),3Hz(d),1Hz(d) 4 11» HB=1HJ==18Hz(d),14Hz(d),9Hz(d),2Hz(d) HC=1HJ=16Hz(d),2Hz(d) HD=1HJ=18Hz(d),3Hz(d), 1.551231) HE=1HJ= 16Hz(d),14Hz(d),1.5Hz(d),1Hz(d) ‘ L . ‘ q{ICH L'CHL’Q) »CHL’Q / I V, 37 i f / a I’ CHS'Q , I“ L—MW ,,,,, Wm] \ vw f @104; mgr—i3 I? B= CL\/\/\ f/ " I OUR/0:4 A0 W Cdsa ‘ CM 10 ...
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This note was uploaded on 02/21/2012 for the course CHE 118B 118b taught by Professor Many during the Spring '12 term at UC Davis.

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118BWin10FinKey - 1. Reactions: (24 pts). Draw the...

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