2006exam-1-key - Organic Chemistry 345 Spring 2006 Exam 1a...

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Unformatted text preview: Organic Chemistry 345 Spring 2006 Exam 1a Question 1 2 10 11 12 13 14 15 Name (Please write Clearly) k’r. Studen 'ID Home Street Number (as in UW Records) Your Seat Number Points Grader’s Initials 10 _ lC) 1b % ‘f H )1. H l (2 Points for each Synthetic Question and 4 Points for each Mechanism Question) P2 2746» Organic Chemistry 345 Spring 2006 Exam 1a C Name (Please Write Clearly) 1. Give the products of synthesis as isolated after workup. . f) 51“, a) H2CH3 , > V Ac20,A1c13 <3? ' PhNOz ' 91> 0H3 ‘9 Pk ~‘H—Cooa Benzaldehyde + CH3CHBrCOOEt Zn benzene *9: C . ‘ ’ 0 = - = - c) PhCH CH op? + NaCN EtOHI HOAC 1014 §H .2. ,8 I” ,o d) . . . Malonlc ACld 110° €643,660 H OMe OM11, e) E Li, t—BuOH - Liq.NH3 / o o I 81* —»‘ (j BQ HBrcat . . g) 0 o '0 - «j (:6 CHggoOH ‘ _ 0 0 h) / 0H Phthalic Anhydride + Methylarnine ————> 0 Q1,” “(I [é i) - .. Ethylamine W Ef— Alli-S? “.43 NHAc 02 MAN: ° BI'2, FeBr3 . Cl Cl PAGE 3 Pg3 Organic Chemistry 345 Spring 2006 Exam 1a K2; Name (Pl ase Write Clearly) 2. Give the products of synthesis as isolated after workup . O R at) .Me CH CHC O EtOH + 2= - = O _ \CHa NaOH 6 / _ b) O CHL P t :0 b + Ph3P=CH2 1:“; *' H“ crime: Hal-I , 4 {P c) Ethyl Benzoate —> FL “0H + En, “fined Aqueous NaOH 5h d "‘ h .- a ) PhCH=O + Ph—C\=O ’PL—CH wee-i $5 1°11 CH3 Conc. NaOH '- e) l-Butanol —> WSCHLCHQQ’H PCC,CH2C12 o o f) Anisole + Acetic Anhydride W» kév 1 ' 3 2 "v COOH ‘ ' 9’ Me£W mom-W COOH 110° . . . - H-H H: Benzylamine —> CHLN '6 ' ACZO , 11) Me—CEN + Cyclohexyllithium —> MQ'IQ, EtZO b j) _ —> ‘ -« O i- 1 Butanol Jones, Reagent oubcHLCl-(L Co 1 CI‘O3, H2SO4 Pg 4 Organic Chemistry 345 Spring 2006 Exam 1a We: P ) Name ( lease Write Clearly 3. Give the products of synthesis as isolated after workup 6 N 3) m-Bromoanisole ——> @aeH‘ 1) Mg, Et20 2) 002 L fl *‘ Cyh'quné3 . 13) i-Propyl Benzoate ——> I” too 0H Aqueous NaOH Dilute NaOH 4 c) O—fi-CHz-COOEt Qfi—Cl’h “o; + 80‘ (7 0 @ d) (“*6 / SuccinicAcid —A—> (,3, ' b e)- Ph 0-8 —> 0'0 6' 3 r MeOH PL3 M 0 Z H 5, —»n< 9 (:0 HCI A g) Benzoyl Chloride +Me2CuLi —> E—Mefl b * c h) NHAc f” A ' b Brz FeBr3 gr 1) NH2 ’ of” —> V 1)HN02 0 M90 2) CuCN r26 j) o o I fij Lithium Diphenyl f’k Cuprate Page 5 Organic Chemistry 345 Spring 2006 Exam 1a Kc Name (Please‘Write Clearly) 4. a Encircle each of the aromatic species and leave the anti-aromatic ones uncircled. b. For the underlined ones, indicate the number of resonance structures. A ©©D®©©@ a 4 1 A a 5. Give the mechanism for the decarboxylation of Ph_fi_CH2_COOH 0 Draw you arrows carefully and put in all charges and unshared electrons. Q64 u c i. _ .. PL‘Ci/$L‘°: c») pla/ :9 ’ 9 ’M W3 CCID'H-(r b ‘ (A) Carefully draw the Frost—Musulin Circle Mnemonic for Benzene. Label all the parts, put in MO levels, label energies, put in the electrons. Then get the Pi— energy. For part B, get the energy of three isolated double bonds and draw the sets of bonding and antibonding MO’s with the proper number of electrons put in. Then add to get the Pi energy. A: B: ' __.-r2‘ ,._ \ .. ,. ._.——»—- H 3; +1 ..I¢-"‘"O 0”,” ’. gay"! % "/ _ “’47—‘- _2" Pi Energy = “2' Pi Energy for the 3 Ethylenes = "g (AWN flu; £01on nit/he. mum: 57%|“) C: Now give the Resonance Energy (DE) for Benzene in units of IBI:_£; 7 . The Hfickel rule for aromaticity requires ‘1 N4” 1-. electrons (give a general formula). 8.7 Write out the reaction mechanism for electrophilic substitution of Anisole by the electrophile Br+. Show the starting material, the sigma intermediate and the final product. Write each structure clearly with all unshared electrons and formal char . In the case of the sigma intermediate, write the most important resonance structure. ;02C N3 ' (C H - 4 H El '0'“ ‘g 9‘ O; J ' 9 1) (3 J 63.3%- KW. 6 9 . Write out the mechanism for the Birch Reduction of p-Xylene. Put in all charges, odd-electrons, etc. Use ethanol as the alcohol. ,{ - V10 5 I - R AIM-IA Wm M”- MLC? MC {4 1601‘ Me— “ WHH’Q; e. fiMM. '8 'u' A L' *‘(N w LfEIZNhT’VF 7—9 6? .L/ tar/r l9 ‘* o» - t-i me M H Me, MsO—rlwu’s.cwkc. M0. or N» M?) MIDI-cal vvto'l‘WV'//"‘) 10. How many peaks are anticipated in the 1H spectrum of each of thefollowing? (a) t-Butyl Methyl Ether Z ; b) p-Chlorotoluene 3 ; (c) l-Bromoethylene 3 ;-'(d) Diethyl ether 3 ;e) 1,4-Dimethoxybenzene 3 . 11. Given the series of acid derivatives, number (1 to 5) these in having decreasing double bond character (i.e. number 5 having the least double bond character). Anhydridesfiasters Acid Chlorides Carboxylates Amides ##ifl 12.In the Infrared Spectra of acid derivatives, which derivative will have a pea at the highest frequency (i.e. most to the left)?fl$ldé* N7 . Which will have a peak at the lowest frequency? (panama? 5 - 4 A cuff/walk (W 13.Write out the reaction mechanism for conversion of ethyl acetate to acetamide by reaction with ammonia. Show the starting material, the sigma intermediate and the final product. Write each structure clearly with all unshared electrons and formal charges. Include the sigma intermediate. 1141.8“! m; Inmdnfii fl :NHB N H3— Coall wt —0(9 . .. l u ~IUH - mm. A!» Mr MIA. me o E E 9 _. a, My C6435?)- " {a 0% ", 9.510 W3 ’6, W4 {/«4 fro-4:4. "' ‘ 'I 4- GUUJX L 6 : . 9~ ' lug/{y " 14 . In Ethylbenzene the methyl peak is split into a +Ylti€i (doublet, triplet, quartet). _ Er ) 15 . An unknown compound, X, is found by mass spec to have the formula of C5H4NC1. It has a delta value of 51 giving a total of rings and double bonds. It has two peaks in the NMR, each split into a doublet. Suggest a structure. ' CI ea ...
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