spring11exam4key

spring11exam4key - Chem. 322b Fourth Progress Test April...

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Unformatted text preview: Chem. 322b Fourth Progress Test April 20th 2011 WWW fluevagé’, '3 7 ‘2‘ Initial of Family Name TA: Lab Time: 1. (05) 2. (05) 3. (05) 4. (15) 5. (15) 6. (45) um Total (100) 3220 Fourth Progress Test, Spring 2011, Chapters Solomon 20-22. 1 (05). Circle and give the most accurate names of the functional groups. I. lac/o o <:>=~~ Cw: m 2 . o , \f/yZé/Ll lLaaélfi Wm” \[67‘1/9 Hem/QW'MM 2 (05). indicate the most (M) and least (L) basic compound. ( i (H) ( ) l l l A) 3 (05). lndicate the most (M) and least (L) acidic compound' OH OZN H < >.QH < >—-OH O < > OH ONOZ N02 OZN OzN OQN ( ) l L) ( ) ( ) (M i 4 (15). An L~aldopentose is oxidized by HNO; to give an optically inactive aldaric acid. Ruff degradation of the aldopentose (1. Bra/H20 and 2. Fe3"/l-lee) gives an aldotetrose that is oxidized by HN03 to give an optically active aldaric acid. Write the Fisher structure of the L—aldopentose. a) :: o 01/) CH :: o (:02 ll H #Nfl3 i o [J ~03 :H 014 O I1 . H "I H I; 0 ‘ OZ/J I/aQ/J 0.: H (/2124) ) ézxcfl #6 Q, / 4m re ”‘ "W"°”"'"'§ 0 ac"; \IQ L‘d‘ Continue on next page if needed. {out/{C 66C (2/ W MW 04 5. (75‘)Write the mechanisms including ail plausible intermediates (no muitipie resonance structures) curved arrowa and formal charges if applicable. {1‘3 C“ O®wéJ .. CH30H o a. (05) GFOH W OCH3 + H20 j \ mean +_ (H! \ ‘? b~P + 05”: 0-008 b- <32 Br + CH3N HK .._—._.. W ii Excess e 0 § / ’>\ a CM? :::. le/ 3 5404 ‘ ,0 Z?) 6445). Give the predominant products if no reaction occurs. Write: “no rxn". W a. NaOH Na BK h 00' --—-——~ 100 0(3 N0 b. CI N02 NaOH Na 2 100 00 I' < > N30“ {Va Ow m . 0: NO WW... 0 .3: C 2 100°C (“r ht) cl Veaan (3; short reaction time - #1 NaNOleCI Q 0” 0 M Q, N 3: N f' 02N < > MHZ 5°C 1 equiv. Z NW“ 1?. 2W ' - a+ r -——--—> m ‘ 0&9“ 9 GO” Q: Q’K‘QQ m. Ea. M“?- h. Q04 ..........;: + /@ twoproducts ~ . M k 1 4/ V14 flit (gr ‘5. «J WNW A acm’rcl) / my: a ‘ 1.002/OH' ZACQO “Q ‘\ / \ A 00H (high pressure) 3. neutralize 602‘” a" Co H 2 Z/ \3 Q“); Ma [© } Mo N2+ ( at he) k. HOCH2(CHOH)3CH=O B'Z’HQO HOCH3(C”0#B (‘92 H co H l. HOCH2(CHOH)30HO “HON H0¢H1(Cflo///3 CW9” 2 2) Haogbaé om * ‘ x “1 ,¢/ awe x a r 1) CH30H/HCI M 0M y 5 . - - W m at: D Giucos 2) (CH3)2304/CH30Na A. 0 fl (0% +/3 J; W "t CH OMe K “' 2 0 H30* ‘ Mo "1 (W M90 OMe " (9‘ +fiJ :74 or g OMe (“(10 r on. o H (fit/7 CHO ... .. C; #5— CGH5NHNH2 _,_ N NH . 0, OH W “N Nhlucgyb. 25:29:) W 3 equuv . mu ‘* 6 a ~MQ / 7,(10). Give equations describing the synthesis of: W ' l / l/Z/(“l /HJ\%@ £54? Wmf 4‘ /(~ w‘vfioW M W 912% ‘3’” mp 46 M L—{a 7%? 0’( of; Q @IMM%W7 WW“ W 1%) (MM, -6.— ...
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This note was uploaded on 03/15/2012 for the course CHEM 322BL taught by Professor Singer during the Spring '07 term at USC.

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spring11exam4key - Chem. 322b Fourth Progress Test April...

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