322bs05_e4_key

322bs05_e4_key - Organic Chemistry 322 hi. Spring 2005 Exam...

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Unformatted text preview: Organic Chemistry 322 hi. Spring 2005 Exam 4 April 13, 2005 Name {MSW/061 KEY Total Initial of Last Name 1:1 T.A.’s Name (34 pts) (6 P‘s) (5 pts) (6 pts) (10 pts) (10 pts) (10 pts) (10 pts) (10 pts) Qfltch/ F— 0 [M ML; 0 1)KOH . .._—> r5 a (firm 2) CHHWCHanCqJEhg +cc§chzcfink O 1. Write the products of the following reactions. (34 pts.) 3) H2N-NH2 IEtOH A owl/a //’N)—~ I 9 0” 0% M MewU- - U NH2 0H 1)NaN02/HCI ___.._._.._._.> °- 2)CuO,Cu20 © H2013 0% \CH3 0 d. [N] NaNOa, HCI (0 j .9 :9 1-1 ==o N—E—CH —CH v—.—>LWH4 NVWQMO“: e. Q, 2 3 ago “a CH3 NaOH IKOH —> 320°C so? Nae é . = 1640 0 "e -O 6 NaN02 I H NH 9 3 C7 CH3'CH2'NH2 A 0 \ ,H H0 H Bra/HZO _.____> H CHgOH OYH (sz HOHZC H—C—OH : —OH | HQ CHQOH C i? 9 e OHS-CHz-NHLi —> 2m \/ MEYM, (I; Gib/0% {MIMI Wang, Mia” fair»; 0 CH7,OH . 0‘2"; H-° 0 NM O§QM I}? OH m H” ‘0“ “a {II-(0f gut/(3% 0% 3 L135; {/1142 (3%"? gm“ 642.- f<0)_ m a, awafir‘mfl’o p. O‘c—H al “‘68”: "NH—Pk O , H H 3equiv ents A? —_————» : M—NHPB H HH Ph NHNH2 Miro” @_ nN~A2bL-fl£\ at u; XML/me 2. Give the pKas ( i 1 ) of the two OH groups in the steriod hormone estradiol. (6 pts.) 0H M ((6-4?) to H0 00 3%A 3_ 20% HN03 250 Write the products of the reaction. What property differences would you expioit to separate them? (5 pts.) 0 ’ Sr VD Om .. M HQ“?! I/“(,C." \ - I, €32“ :00 0/ 0/ 4. CH3 CH3 These quinones are found in human cells in the CHSO W‘H \Z‘fiA Lad-2.; w 0 CH3 ( n=6to10 ofthe M‘JCDAM’W‘AN'WJ. (6 pts.) H3 5 Choosing among o-toluidine éiwz . acetyl chloride. acetic anhydride, chlorosulfonic acid,2-aminothiazole PEN-g] S J NH2 and any inorganic reagents you need. prepare H3 (10 pts.) (9 NW, “tr-3’01} O at, Qua—fin M3 0 sea—N 4:] “at? 6 r Mg? 6 fl?“ “3&5? “W4 C") NH2 _ . CH3 "NH2 1) K0H,Br2 , + (:03 6. H20 CH Write the structures of at least two intermediates involved in this transformation. Remember an intermediate has a finite lifetime. Write the product(s) found if the read?» i§ I carried out in ethanol rather than water. (10 pts.) @ 0 a, / f / 7. Write the product of this reaction. The analogous reaction with 2,4-dinitrobromobenzene occurs at the same rate. In no more than two sentences, what does this tell you about the mechanism of the reaction? (10 pts.) 01 9 0a [CD N02 CHSCH2O ‘00 8. Shell Oil Company has a significant amount of benzene, propene, and butenes available from their refinery streams. To increase the value of these hydrocarbons. they have developed a process to convert these into phenol. What is the other product formed in this process if they used 2-butene and benzene? Outline the mechanism for this transformation. Be certain to clearly indicate the structure of intermediates. Be certain to clearly label the : rearrangement step. (10 pts.) H 0% B-Maltose is a disaccharide. Write the structures of the a and [3 anomers and the neutral intermediate involved in their interconversion (mutorotation). a(+) maltose [at]:5 = +153° f5(+) maltose [on]:5 = +1120 The maltose undergoes mutorotation to yield an equilbrium mixture whose rotation is 25 [01]D = +136°. What is the composition ofthis mixture? (10 pts.) ...
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This note was uploaded on 10/12/2009 for the course CHEM 322B at USC.

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322bs05_e4_key - Organic Chemistry 322 hi. Spring 2005 Exam...

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