322bs06_sample_e4_key

322bs06_sample_e4_key - 322D Fourth Practice Test (Chapters...

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Unformatted text preview: 322D Fourth Practice Test (Chapters 21,22 part of 23) Spring 2006 ’67 1. Indicate the most (M) and least reactive and least reactive toward NaOH . N N N N02 1 5—61 “02' > 0‘ Nor—Z >_CI N02—< >421 No; (L) < i t ') ( ) (M) 2. Write the mechanisms of: 61%?[144 N + BuLi —» N Bu + LiH \\ _ K .. [31,148—774 Nag” we 0...," 0 we, were w \PJOONQ. m“ “771' {‘v \———-%> QO’Q—r " “Q C _ f I CHNHN W HC—NNHCBHS §P14NH Iii-:04 CHOH + 55 Pb“ CH0“ ‘ :40me i i w i” Q ’4 b "‘o -- 4’ n N” C 9:0 .é’ £34011 “‘2’ H0” _ SH ou. 4 d. Maw-“ . . 5g”; .2. #- <:>-5H + CH30H ——H—+—> chrb <§ 1:524?! Nag O 2;» 3 .__ . fleck“. saw 3. A D-Aidopentose upon oxndation With HNO3 gives an opticaiiy active at an am). e Ruff 914M g'cdegradation (1) Br21H20,.(2),.CaCOa, and heat, (3) HZOZIFeS+ of the aldopentose gives aD- 2 odd Aidotetrose that is oxidized to give meso tartaric acid. Write the Fisher structure of the avg» .3 J iatdo ,entose. Show our reasonin . J a mu: P Y 9 CH0 6.02“ 5 a a : ’60 L1 Cu: . L” H z IM/wJZO-‘e OM - [0?) '04; W} 25¢ 1? A5 .’ 9;; ii I c) u ‘/ iii. 4.901% H2011! 99/0324 i ./ / l , 4.‘ 5 a) Arranger in ordebr’of basicity starting with most basic compound: M“ w. -..-.. (a) (b (C) (d) ’(e) ) b) Arrange in order of acidity starting with most acidic compound: . .. H . CH3 HO OH i </ :15 a. C’. OH > > > (a) (b) (C) (d) 5. Choose the relationship that most accurately gives the relationship between the following pairs. D) Enantiomers, E) Tautomers, F) A) Structural isomers, B) Stereoisomers, C) Diastereoisomers, Different compounds, G) Conformers, H) Anomers, l) Epimers, J) Identical, K) None of the above. Use narrowest correct term. H—fi—OH 6- Meso- and D, L f. ,. HOZCQC.HQH)QCDQH CH=O (. I ). b. D- and L—Glyceraldehyde ( D ) COZH 0. H H H0 H H and H H H CHQOH CHZOH ( F ) CH0 h. d. H OH CHZOH CHZOH HO OH and H0 H HO OH OH CHZOH ( I ) C. 9- H H CHzOH VCHZOH i. Methyl-B—D-glucopyranoside and and Methyl-a-D-glucopyranoside HO H HO .t OH H OHOH 6. Give the predominant product if any a. HOCH2(CHOH)3CH=O——B—r2-fl29—> Ham/z (CH0 #13 C02 / 4 1 H N »0 ,4; b. HOCH2(_CHOH)3CHO __)_C_—» M 0:34, (0/ 4:203 CHOIV u .2 2) H30+ 9% _R.c,'/au 042.0 C A-D—Gmwse—W ' 2) (CH 3)2804/CH30Na m0 0 H6 Hz 0% 0N» (“‘10 m ohe O Na 02%} N02 no work up 4.4 .2: NNH—PA f CHOH CSHSNHNHZ _ Ci: N ML PA . 3 equiv 1430+ / \ 0+1 4- C1/3C02H “:7sz Q h. QOCH CH_130H heat < 8’22 9 H — ‘ 2 2 ‘ ’ H25 H :: CH; i. O Na/CH30H > Ho V G a ,4 I 02N Br NaOH Clz’V”/\ 0N“ m“ 2 g —————> .— \/ Br A35" \ ,2 —~ 9» ,1 k 0 be)! ~— 02H + 5 \ / 0 Ngtcr 0 Noah o) I. .~ HOZCQOH + NaHCO3 ——————> 0241' O (34; m. . + A020 pyridine} ’— "1/ o “— Q S 3 0 7- a_. St art ing w ith .benz ene and any. ot: her needed-r. 'eagent .synt hesiz e. : ‘ 0Cfl2. u ICHs 0‘95 CO; H 6'04:a 0020*3 @Cafi “:9 6 =9 . ‘O +- ==§ +44%; cu ' +$0€€e CHQTCB'L on c We N) W; gape“ CHZOH . -- o 4, no; St arting with H SYN hesue ab“ FBOJ’ u m OH OH OH OH #3 (H710 Cub&g )) CH7.“ Na 0 H 0Cl/3 #4- 00! __, MOCH3 _.....-————--r 2 ,_ H CIQCvCi/s 3 /CW3 I c. St arting With H and Br130H2-CH=CHZ synthesize: Egg/MA I .,/ 13m2m=m2 and using any other needed reagent CHgCH=13CHg 3,,» OH: 917. 746 WM, 2, J* '/'\ “ (931%? <\ O\‘ *‘5' 9/4 , r1 / '2' 4 "2 4 (Zr CH CH; CH ...
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322bs06_sample_e4_key - 322D Fourth Practice Test (Chapters...

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