Quizzes - CHEM C3045 intensive Organic Chemistry Name 24 SW lie Recitation Quiz 1 9f23f09 UNI Section PLEASE WRITE LEGIBLY 1 Draw the LEAST stable

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Unformatted text preview: CHEM C3045 intensive Organic Chemistry Name 24% SW lie? Recitation Quiz 1 9f23f09 UNI Section PLEASE WRITE LEGIBLY! 1) Draw the LEAST stable CHAIR conformation of Ct's— 1-( I ,l-dimcthylethyl)-3- methylcyclohexane (assume there are no eclipsing interactions). HINT: 1,1-dimethylethyl = r-butyl HINT: at“: = substituents on the SAME side of the ring (top or bottom, it doesn’t matter which) / Ftp-t“ ngs‘iN MM“ “0 /-‘\-—‘ 2) Draw the Newman projection(s) of the most stable (lowest energy) conformer(s) looking down the C3-C4 bond of 3,3,4‘trimcthylhexane. Cf; ~ CM g? /\/\/ : H ext”; \c/Wct / 3 _ \ 5 / \ 1 CW1) cm; H C C “'5 k [W 7: Clix, C “I u C H H “- C 5 1.4%? m3 “‘56 0.41 0% t (9 @ i h w (113 3 («A e v‘ (who rum-(3 3) What pH would I need to make a solution of benzoic acid in water (13Ka = 4.17) if I wanted a 1:1000 ratio of the neutral species to the ionized one ([HA]:[A‘] = 1:1000)? HINT: Henderson-Hasselbach 3.. i: r {H Hog??? u": “H? ‘— (’H + “$300 J t “' afH:<—IH+3 : Extra Credit: Draw the structure of benzoic acid. “we: l-l Cc; '— Ftv,u1—-W——-——-—'—r—— — CHEM C3045 Intensive Organic Chemistry Name fl fifty” \{ ‘39 L: Recitation Quiz 2 IOIWOQ UNI Section PLEASE WRIT E LEGIBLY! 1) Indicate if the selected stereocenter is R or S. a) b) C) .1 0;. 2— ! / c9 1 a HscxHi'Ca - H .0” / / CH C CH3 C; H c 3' _ H 2 “OH H NHz _ 3 1 It”? if in {vs-evi- 22 3 © 9:» w n .W a .10 J ® 2) Propose reagents and write a mechanism for the following transformation: {0 '\ oi“ vO‘iWI ) I \a /f‘ + } “'5 we) fl 3.). u.) “l _ ’ngi Air—'— quflflfild ‘1 2 I ,/\/C‘)‘k 'i 3) Draw all the POSSIBLE stereoisomers that would result from the above reaction: ‘ 4“ Q. rfl :3 M [3 © 3 (Q L |.\:}I---":‘:c:. (fig /’v . \ V” “a + {HFJ‘HSOOVJN’ wv'Ix.‘ I 2:“ T‘le'l o W bah]? ®{\_fi —5' . I "' kn L9 pr“ [HUG “Fifi/g; “Gr,ng “Job‘ch Lac» cQ be \0 J . . . _ II (3‘ 4-{;n ([43 I Exml credit: The NObeI Prize 1" Chemmry was annomced this morning Who won, and (briCflY) What did they win for? S-‘QH? 1 R0 thfiifvx'Ql/‘rav‘ IUOhL-x {M {1100’ M gawk-«t + -{:V~—c"f7'om : “on! We YL (:W‘c DNA “55 WEE“ F 3° ' K L»: CHEM C3045 Intensive Organic Chemistry Name '1 ' 3”" ' \i ' u Recitation Quiz 3 UNI 1008109 PLEASE WRITE LEGIBLY 1) Write out the molecular orbitals for the pi system in 1,3.5-ltexatriene and indicate which orbital is the HOMO and which orbital is the LUMO. You need not draw complex sketches. Just indicate the number of p orbitals and where phase changes occur as well as the relative energy of each orbital. 2) Circle the MOST stable molecule CH3 ( + I -- O {a} +O—I f I w 0\ 0-0 (I'E I In I W O \ 0*0 OI a I h) CECH : CEN ? Extra Credit: What is a product of a Diels-Alder using 1.3.5-hexatriene as starting material? h-_. we“ l - h t: 1 ft” a“? ‘ r'lt' .\. - ll. CHEM C3045 Intensive Organic Chemistry Namc' 5. -- _ '3 Recitation Quiz 4 UN! 1 li'4l'09 PLEASE WRITE LEGIBLY 1) Give the MAJOR product (only) ofthe following Diels-Alder Reactions: a) fl '- 0 O './J "" C \I ,. D + r): 0 1., 21/1. (LIE) “H x D ,o / c2N ’/ _ PM i: + r 2) Circle which molecule of each pair will be MORE REACTIVE in an 8N2 reaction with l‘: )1“ ‘ ‘ L/‘VOTOS \] JVOTOS (km—05 a _ /‘ fi'\ >k, I a NC] N Br // j BF >k/\Br \ _/ / O u T05 = Ig- Extra Credit: Pick one ofthe Diels-Alder reactions above and draw the relative size ofthe orbital coefficients on the reacting carbons ofthe diene and dienophile (carbons that form new sigma bonds). éa CHEM C3045 Intensive Organic Chemistry Recitation Quiz 5 1 III 1/09 UNI PLEASE WRITE LEGIBLY Which of the following reactions is faster: 1) 2) In the space provided, BREIFLY explain you answer for (I). Do not write outside the box. ill-loci: n; (\ rim-ii“ it" W c 5"" CC " ‘ KN" ‘ Ii" ‘3 \w lr.)-—v‘~'\ '"Q J' r 1‘“: ('1‘ r». rt -'i\w-I\‘.IC I-- r ‘1' "3‘ " I' FF '- a" .I Ll .‘I . - .",.-‘._"‘. [\k.l I ‘-.-\1'i"'-IN12 i- \g’ rafts. Kinney-we . n ’CM- V- \\ ‘~ "r C J 4“";- l+ [- g Q .q ,k.\_,k~3r ('0‘:th nu: .n it.“ no. 5 M1.“ 'i“ l} - rKc-t'um i - if {L~--\_;_I-‘\( f 1-. LS... \J._\U‘L_ ((3 -~'---‘ f‘;('.< 5C3“- ' r__ r I 3 How would on s thesize the followin from startin materials containin four 3' carbons or less (no mechanisms necessary): , J in. SC" - if it -“ 1 C": \ is f.» L4: {u a At. a, “' E" ' n :.":{,1'=l:5" WT: \u . f \ _ w -t I. { 1) Kilt-iii [I r ..-,,.-.I‘- ,1 1.: [I 3, 14-15: ‘-- “h fkkm R)“. H, 2 JJ/ Bu rail; + -—_./’ \I _ x c p' 03 l“ Liw m)‘~*'"- ‘-' “ I I .‘R/ “1% P‘u' ,‘ “H K, ——-'—h /\J\/’ “~13,- fm/KJ ...
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This note was uploaded on 02/26/2012 for the course CHEM 3045 taught by Professor Breslow during the Fall '09 term at Columbia.

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Quizzes - CHEM C3045 intensive Organic Chemistry Name 24 SW lie Recitation Quiz 1 9f23f09 UNI Section PLEASE WRITE LEGIBLY 1 Draw the LEAST stable

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