chem 211 exam - s “CHEM 21'1/47 w ELIAS'30 f EXAM III(10...

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Unformatted text preview: / s/ “CHEM 21'1 /47 / w. ELIAS 11-20-02 '30 f . EXAM III (10) 1) Give IUPAC names to the following compounds. 2556- R ell—c CH 28< ,_ (Cl-b-g—‘C‘é-le—Q‘fi-l (21-12th 5““— F C 3 —. Aanr,n( .CHz—fceH/ . \cu, . - “3“ . é -nanant IE‘ |!I\ \_ ‘— CH3 I 3-nan<r\-‘~~r O 3; 5— dl c‘l’L} —; Y; 5’ if. IJ-Juor0_3_mn¢- 7" ) n 4 -3, (12) 2) Draw accurate structural formulas for the following molecules (next to the name). / allyl bromide / / 7 I § —— ‘5 / \ (3 r' 41/ %/ :/\§ 8 , 5 ¢ / \/ _ . / 4-et_hynyl-1,3,6-cyclooctatriene (a e) ci5<1,2-dipropargylethylene /\\ A ‘,.\\ ./\ .\. é / ‘ C—«(— L H/'- \H H‘ 0 the geometric isomer of structural formula 2e ‘q I I] (28) 3) Write stepwise, reasonable complete mechanisms for the following transformations. Use curved arrows to indicate the bonding changes taking place. Include stereochemistry and identify the major product where appropr? +2, (Iin Liar’o CHz:CH—CH—CH3 + H1 —- 7 + Cl-lJCHz—lO—Cl-h U CH3 ' 1 .19 £9 ”a! I 0;} szch—cu ~cH3 .,.l+——I ' \J L21 “#7 CTEC‘. a; H CH” CH3 *9 Cll‘.‘-[”'"C”‘C”t H - 1 mar? shame 29 3 / IQ le- PAC 0*3 l HCH‘Q ——cH~ — c' ‘- 1 6 (K H H W: C’“3 alt} ~\—J> CH3— (Lil—(L— c ~CH5 ' l mar-E 3H1]? I r26 H- a i ll H" H—CEC—CHzCHa + H20 —~ ? H—Q_ C—CHzCH‘ HQ” ; ‘ ' 3) 'céntinued ........... ;'G\:r / a FOX 5' fut/{tn :5 M P“ a? r {\‘P '7'de 072” 3 C H I» -—‘~.~~__/ more shL/C CTE~ 0*25 "*5 -’> :ICHCH-b #Hw ;:/’ 7‘ - a H Old-x AA,“ JEVVOSPec kin“ Q _ _ _ ' . CH: / 3) Continued ........... cr-b—ozcriz + (:12 + H20 __ 7 + HCi flu-(L ”(Q Mug-90H. . (“*3 c» Ol/p .6) i W. i 3 '5 .-\CH—5—C-=C‘—+l'; +c.lZ:-L —Pl'l""°l+ - _ ‘ -.—-—*>C—“3- g— Cl‘l’L . WW f (35A- CH) (ll /’ c133 Q\\ H10 . / . a C93,?”— cl'lz _—__=>!\CH:>—(i,_acH—L ——PH— rfck W “’0’? \‘i‘ H q (18) 4) Draw accurate stereochemical formulas (Fischer projections or dash-wedge formulas) for all products (include enantiomers) obtained in the following reactions. ' l " M—GH ._ .. i Bf; . H- . ‘ ‘i———->. '3' P . . g H n. rd3f£ W H A / \ C H: H - (‘w i! H2 H‘ CHJooaH H20 H+ H . OH . % 1 00+; Mloln‘l’ .i—i- °l+ 7. 7r _ ‘ / (18)‘ 5)! Predict the major organic products for the following reactions (ignore stereochemistry). ’ H OH' . \\’ Hzé' 0‘3 #fi (E2 only) ‘ ‘ H' a“. NWL 59$va RQ . f 'l 44‘ cl l"-- l l H ~— C. .— C —-cH-——— CH" '3 l l l l1 Cl CH} _ l _ H_ \‘\ OH' 9 \ Cu} 6 ' _. ' ‘-. ‘KMn0. OH' ‘ _ MnO ' :CflcF = c _C—-C—-CH_C ~_. cl» C. c. 4 _ 0 H2 L (5% H2 dil. H20 i4: l I J conc,A C524 ‘ l . ‘ all, 0H CH- eH oH' CH: C 73 l 3 —l' Ca \/ ' 0 . 2H 0 M ‘ H H 3(C11Hm) <— A(C11Ht6) 43* + D—ézo + H—bzo Ni I“. o ' / /§~Q an H = <\ B .. /“' .1 , an \H 3 inf @r J‘lj‘ . r l (22) « 6) . Outline efficient syntheses of the molecules shown on the left from the starting materials given on the right, using any other needed inorganic reagents. Several steps will be required. Show each step and include alt reagents and conditions necessary for each step. ‘1” Ctb (Li—Ll \ ’H — H-c- H r . ,C:C FROM ~ Ctfi—CHfiH—Crh . .50,— 5- 2 CW1? H \CHzCHz—CliH—Cl-b CH; CH: N — l”. M” ( Q—cwz—‘L :‘ C \cHztI-oz —CIH—cl- CH.5 /\ 0’ l w H... ,H Cchr-rch/ \/ CHchzc mom CHJCH2CHz—Br,CH;CH2-Cl . OCHZCHQ'CI “Han Br’ ‘8: \fi‘f m VJ \AL ” \ It 1 \ / H H/ ’ cHB'g C. f_ C 2 c— (—‘— ' — ~ - C“ QuErL/ \c/ CHZ‘F'LO 0H ’ Chi . I \CPZCHCG p1 P: S ‘1 5 c“ ref/L! C“: 2’ / ,QE Q-ch fr. , ‘ CH§?L L z L l /\ j [\fUr H Cl rH‘scH’ZLHé—CEC—H‘ _or,l_ hf- l A / ‘7: V ‘ [a _ l / N ' row..C<-C2\\>' ’H nrH/ / \ \ / ' 13 ,1} ' A H Chzcflrchrfif 4. c H a c r+{ In III, ‘ I J _ J ,- v I .1“. E7 " VIIIt'd ff, ’4 E-v‘ “IQ/12) 7) Circle the one(s) which: a M I “I . {IVW\ e a) is the correct order of decreasing bond length. k lax-J . 3 i=1" ' $— ‘I‘il" ”WWI” T T 1 .2. Q r / 3<s1<2 2‘>1>3 295}. {$9 1“<2<3 . 3>2>1 2>3>1 2<3<1 -1>3>2 (s the corgrect formula for a molecule with five centers of unsaturation (CU: S). / l W L‘ ’ ' Cf“? {AI 1" Cletza3 CIasz r. Clsts (:17st C17H24 C17H20 b- , a9”! 3 —33‘ A 9‘ IV I” 3: V I. s I? WK I t \ ) is the correct order fOr' Increasing heat of hydrogenation (AHIII) III; IIIIIII Lg -l.;:5;:_;;,s 5 5;; I I , II III.II mu: '/€;S JV” hkif‘ “ ‘ Lt . ‘ ‘ 5k..|l bf I III I I. "F. .- .—.<“'- 1.<5<3<2<5<4 6<5<3<1<4<2 '1 <2I<41é§k<5<6ul ‘ 4<6<1<3<2<5 5<2<3<1<6<4 i4<5<2<6<3<1 q3<6<1<2<4<5 4<2<6<1<3<5 5<3<1<6<2<4 a .: W”) lIr-MII'J In] 7 ifii'm} >_- d) a e the orbitals (atomic, AO OI hybrid, H0) whose\ overlap (by LCAO) forms the vinylic carbon— drogen sigma (0) bond in alk- nes. 3_ C :2, C _ ,5”; 0,1 _ . 1k F‘- 4<5sg<q<.6<1 sp HO & sp HO sp3 HO & sp3 HO 2p 2p AO / HO & 15 A0 ' Ila—g? ;. ‘ L?) is the correct order of increasing acidity. “I" "I If? I . ‘ " C ‘7 j ——J2:él—_H H30 —C—:C—«l[-i/3 —I£—$—H C “Q i 2 g 4 ‘H- (V 2<3<1<4 lé4<3<2 4<1<2<3 3<2<1'<'4 2<1<3<4 4<E7I<1<2 (”'4<1<3<2 l [JI‘ -ll ‘ . \ (I ' {I {:Cv-CP‘C-C‘Cr-g' 3&5? TC —C~< ICQi OM would exhibit geometric' Isomerism. I/ I \ W (\JJ ‘I‘ hr“) 1~hexene / 2- hexene Y 2—meth\y ——2 hexene 3- -ethyl-3- -hexene ( vinylcyA- . ' M “3_:_ _ _ HM \ \' C‘C CI '7' @possess molecular orbitals (MO 5) constructed (by LCAO) from parallel overlap of p atomic :3 orbitals (p A0' 5) (more than one possile). 5" alkanes cycloalkanes ' @ [email protected] alkyl halides ‘(t‘nr—I: (~(-( ...
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  • Fall '06
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