322B_4TH_PRAC_ANSWERS

322B_4TH_PRAC_ANSWERS - 322i Fourth Practice Test(Chapters...

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Unformatted text preview: 322i) Fourth Practice Test (Chapters 21,22, part 23) (i Spring 2008 N i1 k CH :: M0” 1. Write the structure (choose your own example), (1/ Q a. Ester CE ff” 7 5 b. Lactam /"" - c. Oxime CH: Put—NH" Pl. d. Sulfonamide C" c: A e. Thioacetal'mg ”‘5‘ f. Osazone -/ E 5—. NWNH Pl: g. Imide \ 9 h. Carbamate L—J i. Dialkyl carbonéttk _ . . .. a. ._ \ . , 7 __ r Lia/NH Q jW’Q Cflgamfi/Néfijlz Q“ C? 2. Writ? the mechanisms of: 0 Cr OH“ C- HC(O)(CHOH)30H20H EH: 0 H20 0 _ _ CH: Hog 6H ‘ Hot N ~01! «-——9 C, . fl i140 H- H éZL-gf‘ “N f c Ocmo cfiofl . - +- YHk/J’ 14353 H \O, 9H2 3. A D—Aldopentose upon oxidation with HN03 gives an optically active aidaric acid. The Ruff degradation (1) BI'2/H20, (2) CaCOs and heat, (3) H202/FC3+ of the aldopentose gives a D—Aldotetrosc that is oxidized to give meso tartaric acid. Write the Fisher structure of the aldopcntose. Show your reasoning. , 4-H =5 G Hit/53; fiat)” 9‘72 ’4 . . 7 OH‘ 0” *O‘fliz é (Di—f éx. 0 H \\ CH: 0 02 L]If 0U; Max/“.3 0: 0H ; a" i—/ Cfion ' cagj a) Arrange In order of basicity startinng with most basic compound: (do >( 19> (0’)) CC)>C:J (a) (b) (c) (d) b) Arrange in order of acidity starting with most acidic compound: Q—OH . (:>—CH2OH (60> <c)>C<9>U OE; H3 [email protected]; (a) (b) (C) (d) 5. Choose the relationship that most accurately gives the relationship between the following pairs. A) Structural isomers, B) Stereoisomers C) Diastereoisomers, D) Enaiitiomers E) Tautomers, F) Different compounds, G) Conformers, H) Anomers, I) Epimers, J) Identical K) None of the above. a. Meso- and D, L f. H—C—OH H020(CHOH)2002H CH=0 II x‘ I) H Cw—OH . t L H and H b. D- and L~Glyceraldehyde ‘ CHQOH ( D ) c. HOC' C 02 CH20H( )CH20H h CHO CHO OHCH20H OHCH20H H0 and OH H H OH CHQOH CHQOH (I ) OHCH2OH OHCHZOH i. Methyl—BD-glucopyranoside and Methyl-a-D-glucopyranoside c H > 6. Give the predominant product if any f? / a. HOCH2(CHOH)3CH=O B’z’HZO #0 cm; {Cf/0 ”/3 592/9 0 *2 b. HOCH2(CHOH)3CHO w H6? 022 [0/6’ fly away C 02H ” ” 2 H 0+ ) 3 CHI-20"“ _ A c, WWW w 0mm 2) (CH3)2804/CH30Na a“: CHQOMe d dgflm wt? 1"; e_ BrrBC?W:: Nchog Na 0m©_, mg HC’... NIL/HP; f OH w J;— NNHPé 3equiv $ Qw OWN—Hm CCH3 9' n O h- heat *’ . Q—OCHQCHL-‘SCHA H2 -—> \ i3 011 CHZCH :..~ CH2 i. 0G0 Nat/CHSOHb E _ _ H'0”<‘¢;>‘“0# C)2N BF NaOH yszq: OHUJa) I3»; Br A k. 0 / 02H + —-—+ ' Q4: >3 A IVUI I I N2+,CI“ o I. 4..- H02CO—OH + NaH003 ____.__.. was C«<}>—- 0:45 ITI. d" .— ._A ,.. . - I Q—OH + A020 my. (K />—C>gu.h¢3+ CfgC-OZ ) HN,\£> ”‘“ 0 3 n. NR . Q—OH + CH30H2l ~—A—3> @" 39/2 0365* O 0 HB - ‘-' ' : . Q—OCH(CH3)2 -—-—c ”C 5* {12>— ‘W “i 32 (”(C’Q)Z Br HzN’ [1 . “ II . NH "fl ---- G—ca + NaNH2 q :3» \ / <33 7. Synthesize: a. Starting with benzene and any other needed r eagent synthesize : OCH OCH 0H 33' "-9 t (:01! ,_ COG? . C023" 0 A/ ’5 . CH . . '\ § .4. CH3? / 3 2? fi' ' / .4— 5054’ \/ :fi 002043 $65:le H 2+, w:- Nile 02 O __. @4- C02 % I- O’Llcjflfda 7 C) 22$? 5: K 0-55.32 -+ Hawaii/flax? + (gr + ”’2 CH2OH CH200Ha b Startingwith 4W0H Synthesize <13?! 0” 0* OH OH OH OH {3%) (Hz 5H Crag“! 030(3-I2. 0cm,» IN mac/(g 9 Axe-CW act-{e ' (6.2;) (”a ‘ .3) 'Oh’ 0” , "'2' C) CW: x C5< 8W c. St art ing with H and Br13CH20H=CH2 synt hesiz e: ,— 7 z} {pa ,0; <0 ed Q, him /C"IZ ' > ‘ ‘” I 4 1'3 and using any other needed reagent \\ 013042043042 CHQCH=13CH2 using any needed reagents. ...
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