2006fianlkey - Organic Chemistry 345 Name(Please Write Clearly Spring 2006 Final Exam a_M Student ID Home Street Number(as in UW Records Your Seat

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Unformatted text preview: Organic Chemistry 345 Name (Please Write Clearly) Spring 2006 Final Exam a __M_ Student ID Home Street Number (as in UW Records) Your Seat Number Question Points Grader’ s Initials Q 1 L _ V? (3M3 __________— 6:0fi 2 2C) 3 25 4 f 5 5 _ 6 S 7 S e 5 _ 3' 9 _— 3/ 1o ._ 5 11 ' 12 “,5 éwj' cap 34- /oo WDX. (2 Points for each Synthetic Question and 5 Points for each Mechanism Question) Pg 2 Organic Chemistry 345 Spring 2006 Final Exam a Kc Name (Please Write Clearly) 1. Give the products of synthesis as isolated after workup. a) Acetophenone + MeZNH+ CH2=Q HCI . fL—%&H;'C‘4£N Ma‘- Li, t-BuOH M; o ' MeO __> e / 1:) Liq.NH3 b) MeO “‘9 c) or NJ cn/ , F d‘floH H04,H d) r D-Ribose —n> HCN,NaCN e) Dilute NaOH __ “Q Ph—C-CHZ-COOEt 101' I H3 0 g (i? o f) , LD-Pk. | Lithium Diphenyl (c11sz Cuprate 2KNH2 Liq NH3 Pkgcimz—cgacm' PhC-CHz-C—CH3 —> 1/ O PhCHZBr g) 0 0 -c-*Of4€ h) Ph-N=C=O + MeOH > flfl’“ :6 i) V QNEN' —. @N‘NQ’NME‘ + N,N—Dimethylaniline O 0 j) . __ , NH MW 57) out FM 2)BenzW|odMe O Pg3 Organic Chemistry 345 Spring 2006 Final Exam a M \b __*(V___ (\& Name (Please Write Clearly) 2. Give the products of synthesis as isolated afler workup a) r .. » ' I Om H202,Methanolic|\laOH Om ($043 /—CooEL/I b) Ph-COOEt+ Ethyl Butyrate ’NaOEf’ PL'S“CH . c p VoH L c) Phthalic Anhydride + Benzylamine —* ° l—pnwa—V I . . 0 _ ———)» =L‘»CooH 1- cHII3 d _ _ .. CH3 ‘ . e) Anisole + Acetic Anhydride '—-—> AICI3 PhNo2 C“ 91'! CR3 OCH CH ' f) 2 3_A5 a; + QH¢CHEZ E 1 HI ' ' mm” W "HVOR 9’ ' PhZCH-Br —> -L H20 Benzyl ——'_> FoktooH , h) Alcohol Jones Reagent CIO3, H2804 O ZnH . +_ Q J) A @91- l MK. Me M m Pg 4 Organic Chemistry 345 Spring 2006 Final Exam a Mei Name (Please Write Clearly) 3. Give the products of synthesis as isolated after workup ' OUT! a) CECOOH 1. HONO . _ or {fax NH2 2. Benzene A _ I- ‘ w b) Cumene Hydroperoxide DiL H2304 pLoH t cfirg‘r‘fi? _ \3 . 0 0415, c) b + Ph3P=CH2 . 00be d) D—Mannose _—> D11.HNO3 N . KL CI' OOH. Jog] —, b e) CuCN L“ 0 ' 'xeoDEPf . . NaOEt,EtOH - f) DlethyIAdeate —> O I H'N-lk oJ “(g—uh g) _ . -- l: Cyclopentylamlne —-—*)* ‘ AC20 1‘) ' ' ' —> L-C'Wh Benzomtrlle + CH3L1 EtZO 1’ 1% COOH' i-Propyl Benzoate j) a 1)BuLi ' Y 2) Benzyl Bromide' . 5 Me i _ Mei/"cmh Aqueous NaOH ‘ Page 5 Organic Chemistry 345 Spring 2006 Final Exam a Name (Pleasg Write Clearly) 4. Explain why beta-diketones are more acidic than mono—ketones. Use 2,4-pentanedione and acetone as your eXamples. Draw all relevant resonance structures. Put in all formal charges and unshared electrons. (A concise answer is more likely to receive credit than one which is dif use) “SMMQQ 8km Jive-(- +1fker-AAM five-c0” {Walsh ES mm . Monomef u :75} Q { g0“ gwfiww - ~ — — <4 4 - ou5$=ef4'% C359”? Va” :3. 4 :6.- 5-" .0; :‘Q / ’9: '-' r ,3 CH cflcflgQerés l& :9: y -..é5 5. Give the mechanism for ' '- Ph-E-CH2-COOH decarboxylation of 0 Draw you arrows carefully and put in all charges Efi and unshared electrons. ’LH ca *\ \ \ o FIVE? Gar-=6: PL§¢ 2’ 95 9:] C5. —+ .,o:H LP? 10H,“ 5 .1 .0- 6. How many NMR peaks are there in p—Xylene Q~ , in 4-t- Butylbromobenzene .3 , in 1,4—Di—t—butylbenzene 2. , in Diethyl Ether 2 ? 7. In Ethyl Ether the methyl peak is split into a f}, k (doublet, triplet, quartet) while the methylene is split into a. ux¢ e . 8. The HUckel rule for aromaticity requires. ‘1N'f2~ electrons (give a general formu a) while Mobius molecules and transition states require electrons. - _ 9. An unknown compound, X, is found by mass spec to have the formula of CgHm. It has a delta value of 4- giving a total of q rings and double bonds. It has two peaks in the NM , each H3 [fiCCP/jt unsplit. Suggest a structure. C n. 0K2 Page 6 Organic Chemistry 345 Spring 2006 Final Exam b keil Name (P ease Write Clearly) 10. 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 charges.-In the case of the sigma intermediate, write the most important resonance structure 6 MC) :gi/oH b \HMQ r #9 Mg; *9 W k/ \ ,. , H Ff" 1‘8.” 5&4 11. 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. . . "Hp .. FINlfi /NH) (6 CHa~Q~§E7D /> 0043’? " ’9 CHJS :561‘ U \Ot 0: " 5; a -- (“Way 12. Which has the greater carbon 1 double bond character, acetyl chloride or acetamide? gcefi) (1% (hf/(9.9 Draw the resonance structure accounting for the diminished double bond character: (:2 -w aufasvk ( {(95 h 9 ...
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This note was uploaded on 03/27/2008 for the course CHEM chem345 taught by Professor Zimmerman during the Spring '03 term at Wisconsin.

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2006fianlkey - Organic Chemistry 345 Name(Please Write Clearly Spring 2006 Final Exam a_M Student ID Home Street Number(as in UW Records Your Seat

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