fall-07-zimm-exam1-key

fall-07-zimm-exam1-key - Organic Chemistry 345 Fall 2007...

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Unformatted text preview: Organic Chemistry 345 Fall 2007 Exam 1a Question 1 2 10 11 12 13 Points \HHHHH ZJM MrWLCU/l Namefgfléase Print) Student ID Home Street Number Grader’s Initials Two points each for questions 1 through 11 Tens Point each for question 12 and 13 (as in UN Records) Pg 2 Organic Chemistry 345 FAll 2007 Exam 1a Kerr Name (Please Print) 1. Give the mechanism of decarboxylation of a beta—keto acid. Use A for your example. H+ Ph—C-CH2-COOH ,»CH:- 22.: (’cH . . II «(I K«her —e// 2 0'. ~ -0 O A Pk {P J _Ffly lob In Cf? ' Fm (% 6% :91. Haze» “M of f :9 deg 4M MAJ-(I5, Mm” SP5”) :3 no Witcd IsMfif'MMn} , 2. The HUCkel rule for aromaticity requires flcf+2 electrons (give a general formula). 3. Write out the mechanism for the Birch Reduction of A. Put in all charges, odd—electrons, etc. Use lithium and t—butyl alcohol. ow, :b‘m_ ,- ML 3' OMB Fa \ I! GI. i - is :14 ME ti? .4 M It FIRM ' Ia .. / mama we: hflw‘ . ‘5 “(a W‘J‘iéfififi e, >CLPp‘FCJ) .6— I ‘ EWFMMJQM 51R I I I 4% EnCircle the a omatic annulenes and underline the anti—aromatic ONES . immaon ~------"" I-—...—-- _ 3 nun—h.- 3 5 E’ :2. “L. 2‘ ’7 .7 4b. Under each structure in 4a above write in the number of resonance structures possible. 5. How many peaks are anticipated in the 1H spectrum of each of the following? (a) t—Butyl Methyl Ether :; ; b) p—Nitrotoluene :3 ; (c) l-Bromoethylene :3 ; (d) Diethyl ether 3 ;e) 1,4— Dimethoxybenzene 3k 6. In Ethylbenzene the methyl peak is split into a ffiqghi (doublet, triplet, quartet). Pg 3 Organic Chemistry 345 FAll 2007 Exam 1a Name (P1 ase Print) 7. (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. B: HE . -c) "”"'<3 *1? Pi Energy = -8’ Pi Energy for the 3 Ethylenes =ibg C: Now give the Resonance Energy (DE) for Benzene in units of Ifilz‘q _fl (of 11p] or ‘2.) QU&« 8. Write out the reaction mechanism for electrophilic substitution of Anisole by the electrophile Br+. As usual, put in all charges, electrons, etc. . In the case of the sigma intermediate, write the most important resonanceust ucture. :b/1fl& Me. '- 30? Ma?- seen (95 Bf: H 3‘“ m 9. 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). Anhydrides Esters Acid Chlorides Carbox late Amides _3\_ guy—l 4 g _‘1_ .0 I - - - . - - Amie . n the Infrared Spectra of aCld derivatives, which derivativeCA _ will have eak at the highest frequency (i.e. most to the gliwd¢0 left)?AUf(fi)Wlde . Which will have a peak at the lowest frequency? Emuggg . 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.-_ =NH . NH .C_ W3 ‘ l E Hoyt M442» . a“??? =—"*1’3*"——‘> 0945’"e,'fi-9CN’-QHJ 5?; r Hnefwicé :6 ‘ 0' v I Pg4 Organic Chemistry 345 FAll 2007 Exam 1a __Ke-%___ Name (Plea e Print) 12. Give the products of synthesis as isolated after workup. a) OMe / OW Meg Li, t—BuOH Li .NH Me CI 3 b) NH2 JON Q 1)HNo2 @ a a Meo 2) CuCN M L‘ PhCH=CH~C=O + New Pk?“ “Caz—'10: “'0 c) ~Ph EtOH, HOAc CA, 0 d) _ Co Benzaldehyde + CH3CHZCHBrCOOEt Zn! benzene PngiH CH 05:1” 0H e) Malonic Acid Tao—ma- 09450001-0 O o (53" f) —————————> BQ Hana o g) o b CHagoofih w o o h) ‘ 4 E' PhthalicAnhydride + Ethylamine —> _,___ M f Cue” . H i) Benzylamme +5 pL‘QHLU..S-cu3 (awkknu A020 0 "A: NHAc NHA‘ ‘ j) RY Brz, FCBI'3 <11 CI Organic Chemistry 345 FAll 2007 Exam 1a / (\ 6 Name (PleasePrint) 13. Give the products of synthesis as isolated after workup. O a) Me EtOH + CH2=CH-q=0 N 0 CH3 30H b) O C Hg. 6) + Ph3P=CH2 c) Ethyl Benzoate —-—-——> COD H + E‘FO Aqueous NaOH PhCH=O + Ph-C\=O 1 CH3 COUC. D e) 1 -Butanol PCC, CHZCIZ 0 HQ f) Anisole + Acetic Anhydride $ AICI3 PhNo2 C: o CPS 9’ Dilute NaOH O‘cnwb ll O—fi-CHZ-COOE’: o O i3 '3’ h) H202 NaOH, MeOH i) —— . . .. Q. Me—C_N + ——s- t O Cyclohexyl 11th1um Etzo M If) j 3 1-Butanol C7013 C “LC (41.00 0 H Jones' Reagent CI'O3, H2804 ...
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fall-07-zimm-exam1-key - Organic Chemistry 345 Fall 2007...

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