2004final - Page 1 Ke ‘1 organic Chemistry 345 Name...

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Unformatted text preview: Page 1 Ke ‘1 organic Chemistry 345 Name (Please Write Clearly) Fall 2004 Final Exam A Student ID Number; and Home Street and House Number (for idem-.5. fication purposes) 1. Give the products of synthesis as isolated after workup Give discrete product structures). ’[ 2 Points Each] on a) Anisole ' PhNo2 _ C a 79 \ b). Benzylamine —---)-_ plfilfi— ~C M5 A020 . D Q Li, t-BuOI—i ‘ .__,._.__>. - Li .NH 54‘ :2) M90 E q 3 Mt _‘ d) Ph-N=C=O -.UH-—9-°E{' EtOH b ’ 0143 6) p-Bromotoluene 2) (:02 a” f) l-Butanol —. M13ch H,_c.:+=o PCC,CH2C12 _ :9 Benzoyl Chloride + MczcuLi ...._..._._.._.. Pk‘i‘flv‘f‘ .. ,0. — , h) PhCH=o + Ph-C\=0 _______., pk-cfi,.CH 3 P11 CH3 Cone. NaOI-I i) . Benzoyi Chloride + Dicthylamine ._.._......._y.. PL-fi‘fi’ Eh , 9 fit an/ 1') N H CuCN 7 / oi CI Page 2 E . Organic Chemistry 345 Name (Please Write Clearly) Fall 2004 Final Exam A 2. Give the products of synthesis as isolated after workup.[2 point each] a) CI I HHL A)” 1.— ' \ -l~ k» G KNHz, Liq. NH3 (2 * * Isotopic Carbon ‘ 4; h EtOH . . - __ C'- b b) Benzchcud drop H2304 H O c) Acetophenone + Brz NaOl-l b d) Ph—"CEN _..__._....... ph-C’Mf, .- MeLi b 6) Methyl Benzoate NaOH EtOH 8° Et /- “5”” e56 fl ‘0 coca El“ 0 -—AJH/ El" )2 Urea NaOEt _ 1 “it o o EEO éjuo» A Cl 1‘) fimz dil NaOH \ -. H20 Y .i) \Me ‘| H ML 9 CH CH CH COOM ———> 3 2- 2 e 1)LDA cfl$cuch—COBM(. 2) 131-1 E1. Me It “02 n my «rd/MC l/ A - a.“ < \— H.~M( Page 4 m Organic Chemistry 345 Name (Please Write Clearly) Fall 2004 Final Exam A k 4) . Give the products of synthesis as isolated after workup. [ 2 point each] a) Toluene + Benzoyl Chloride Nels PHNOZ TIL? . , “:7 Q00” ‘9 b) D-Ribose —_~—+ Dil. Imo3 E a H' 1) NaN . c) Ph-Q=o 3 Pk”;- g: a c1 2):: Benzene o ‘3) Me MeOH ’ + CH2=CH-C=0 ————-—> - ‘GH3 NaOH 0 e) ' - . Anisol ——-—I- + —-T_' 6 HI A PAOH Me 0 _ ()0 f) 30% Alcoholic KOH @ “+1 Nflfwa-pk‘ ° L 3 Ert . f -c... cufcbb g) Acetophenone + BrCHchOEt 2M 5” D h) PhZCH-CHO + Methyl Vinyl Ketone H We KOH g? 0 O ,L A i) PhfiOOl-l O D ‘ Cng j) lbw“ __Br2 Hgo" Page 3 2 Organic Chemistry 345 Name (Please Write Clearly) Fall 2004 Final Exam A 3) Give the products of synthesis as isolated tcr workup.[2 point each] - _ ~———|" .Qm. a) _ Ph E CHMe2 DZO’ base FL, I c me) l b 9 é-uusj b) . Phthalic Anhydridc + Ethylamine ———- <1 5 Q00 B NEN / c) r C + HsF'Oz “ Br Br 1)KOH fifi-Wfi’ . d) mm 2) Benzyl Iodide g n 0 - 0 o H - p ccep!‘ ' ‘ 0 LC. oIJ coon D thcf Plow-“4' COO”- COOH A g) Me arc—H 2‘?F’C ’5 MQgH-g'CHs + CH2(C00E°= NaOEtEtOI-I 1 ° 0 a ' QWETDL h) MBQC-OOH +— 0 H+ fin—CH —W2~$"P1l éu 0 i) PhCH=CH-C{=0 + NaCN Ph EtOH, HOAC G o . D (“>7 H202, :- Page 5 Name (Pleas Write Clearly) if €31 {3 Points each for questions 5,6,7,8,9,10,l 1,12,] ‘ Organic Chemistry 345 Fall 2004 Final Exam A 5. (A) Carefully draw the Frost—Mueulin Circle Mnemonic for Benzene. Label all the parts and put “ in the MO levels, label the energies and fill in the electrons. Finally, get the Pi-energy. For part B, get the energy of three _ isolated double bonds (i.e. three ethylenee and draw the three sets of bonding and antibonding Ho's with the proper number of electrons put in. Then add to get the Pi energy. E: A: “Z— A—l, 0 ‘ 41b“! . . I _ - --4bv-‘2. Pi Energy = "Y Pi Energy for the 3 Ethylenes = #6 C‘Wyy 8W3 (av-.6 «r;- C: Now give the Resonance Energy (DE) for Benzenelin units of WI: 2. - . . . of '2. l 0f "'_ e 6. The reachon of cyclohexen-Z-one wrth Phenylhthlum proceeds diffemnfly<han Dunning: Diphenylcuprate (i.e. Pthu' Li“). One of these proceeds via conjugate (i.e. 1,4) addition and the other by 1,2-addition. Give the product structures for each: Phenyllithium Product: Lithium Diphenylcopper Product: 0 Pk m '3' Lark 7. Give the mechanism for decarboxylation of a B~ketoacid. Use Ph'(i'CH2'COOH ' o as your example. Draw your arrows carefully. Put in all unshared electrons and any formal charges. MECHANISM: $5 \ CHL- H Hz. a . pL~C/K_/\Q::b? 1 ut B WC” «6% :37 J> “Row '2' v F“ J h>~r°fiéxv-e 'r-H n -' 8. Encircle each of the at; O u‘ ar atic species and underline the anti-aromatic ones. 6 ‘ e I V D _ O __._., O ' _—.___ oil) - Page 6 Organic Chemistry 345 Name (Please Write Clearly) Fall 2004 Final Exam A b 2 9a. A pericyclic reaction with an odd number of +/- overlaps is MEL [as (Hiickel, Mobius) 3,\ while one with zero or an even number is Haing (Hilckel. Mobius). b. A transition state (ground state) with 4N electrons Helen J}? BES‘.(_(Hfickel,Mobius) ‘I S‘fl'wev ¥\ topology in order to give (allowed,forbidden) reaction. (SW V‘L‘.’ . c.The co rotatory closure of trans,trans—l,6—dimethyl—1,3,5-hexatriene leads to a W :(\ Mi fl (Hiickel,M6bius) transition state while a disrotatory closure (madden 'affords a ‘ fl gkfi ( IIiickel,M6bius) transition state. 5:4- 0,“ w w w “4 1%; J 10. Write out the reaction mechanism for electrophilic substitution of Anisole by an electrophile 7!“ M E”. Show the starting material, the sigma intennediate and the final product. Write each structure clearly with all unshared electrons and formal charges. In the case of the sigma intermediate, write 42% Won important resonance structure. w» /Q’°i”“ 5"?" all. . C?» -> [iii '9 © E 4- " I5 A . 4’ \ .ar' 11. In the NMR of molecule A, how peaks aret ere ? Secondly, How (is, are) the methyl peak(s) split? bbfit 2 is: Singififié v . Finally, What splitting is seen or the remaining aroma 'c {flogens‘l c i5 e» - is l “Jodi-i819. ‘V\ CH3 on We ufit oh 0 3'51 O o 12. '3“ hv . ___ - Jr \. ‘Y ‘_" “" L Ph Ph Ph _ ~. 11 r 11 Give the bridged intermediate Give the Final leading onward to the final product Product ...
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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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2004final - Page 1 Ke ‘1 organic Chemistry 345 Name...

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