322bf06_e2_key

322bf06_e2_key - Professor T.E. Hogen-Esch ?' 9 Fall 2006...

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Unformatted text preview: Professor T.E. Hogen-Esch ?' 9 Fall 2006 Chem 322b Second Progress Test Initial of Family Name Name: a TA: Lab Time: 1.(10)_ 2. (10) __ 3. (05) #— 4. (20) _'_ 5. (35) __ 6. (20) #— Total (100) _ fi\ M54 I’m/0) D\ A (5) PhCECLi, PhCH=CHOLi,©—0Li O—OH CNLi (3(OU xx () () () (L) (M) () O < ) (M) < ) (L) ( ) OH I“ 1.(10) In each of the following series indicate the most (M) and least (L) basic: Wit, 2. (10) In each case write the most important missing tautomer. 9‘ 00H 09% CM (30 Do 3. (5) Circle and name the functional groups: 1 M /7A,€i7 (“g /, OH") R) CH2=PPh3 gig/e 0 ram. 4. (20) Write the mechanisms (curved arrows, a_l| intermediates including formal charges): a. CH2CI2 QOH + —» WQOH Include the electronic structure of the nitronium ion and give only the most important resonance structure of the key intermediate. ""‘"' ""—""" /0‘ - ‘ a ' - _ \ ‘ + . ‘ H+ (EH MM; “EH ' (A: {10/ w H [—5 or U E B ,.—_ {grow k/ // I : /O\CH3 H30+ <3} CH OH b CH ———> @040 + 2 Cl-IGOH " C73 :g/CHs f» ‘ fl T (/1 . ‘5 - Hui _ + 1+~——-C’H; ~ "‘ (Ii-"OCHJ " i A; CH 6H ‘ l . l _U C 37 j <\_/ [49' H _ ‘6; C1707 2... ‘ _—_— <\ / LC 1 M CH: 0(a); .5 <\ / $H~QCHJ> + I @g 3? H x 3 h’ +_ [4,20 a_ - "D . H2N—© + CHaCOCI Alo3> N0 k‘ M“ eKaffl-f '}5/ 1% b. C ‘ i" ’7 :> HD—©+ Brg —82> HO \/‘ > H3 CH’E CH3 monobromination thv‘ 1,42%?) 0- H3 +n-CaH7COCI—1A'C1 2—»“(H9) HCI/ reflux hv 0K abut“ (a? Cunt) Mfr/07¢ (/13 )5C1/3) CIL/CHZCH; 4‘ d. H3CQCHQCH=CH2 + NBS —» @/@C -_</_ l 5 «IL “543. 1.LDA 2- (CH3)2CO _ 0 e' <:>:0 —> 3 neutralize> H ,<(C 3).. HO f. 4—- . 7 Demo + CH2=PPh3 _____. CH -4fi/2 C 4 a3 D25“) M4” m FeBrs H O . . monobromlnatlon l»/:w& Mi 0% amfl‘v. (ad) I base H2/ NI 0 H h. 0 +HCN —> .—> hr pressure /‘[g Iv % l 1 .SO 2. Br I f i. o —3> —2> / #0 3. H20, heat — K m ’\ CH30H 0‘ j. 0 > — H+ OCH3 ' \ v C/ k' QCH=CHQ+ConQ HBr ——> f3) C #3 | . > OH _. CH2; heat hv 00mm?) 2 + 02 6.(20) a. Synthesize using the Wittig reaction from toluene and cyclohexanol (hydroxycyclohexane) as the only carbon sources and any other needed reagent. \ @ -/ ./C”3°QN8§ 9047 \ /CH: O i -~—--—> fl [ \ <3 J/W’C / t. “A OH , ' 0 FR“? ' _,_ 7:; K r' (7 WWW? Owl m 0"”‘3 " 4 , r, I f 774 a x- 3 N05 ~ ) 3 —C* a Hm @ o #3 'WA ‘Qégk :9 50.4. t: 3 00” [(2% <3: NM {2 b. Synthesize from cyclohexanol and benzene using any other needed reagent: O H , .. N55 ’ a C7366. yak, - W <Z><y381 0 fi 0 5 Ar "" , m 07% <- zjwc‘C /’ O H IL/ZOLO O: G 4— _ C. ~ \ H Q H—O _ A _ OH_\/ 01%! c- M \ , / :4 l/ ...
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This note was uploaded on 05/07/2009 for the course CHEM 322BL taught by Professor Singer during the Spring '07 term at USC.

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322bf06_e2_key - Professor T.E. Hogen-Esch ?' 9 Fall 2006...

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