Quiz 1 Key - Autumn 2011 Chem 2378 Quiz 1 Name kE ‘...

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Unformatted text preview: Autumn 2011 Chem 2378 Quiz 1 Name: kE ‘[ Version 1 Section: Q1. (5 pts) a. Draw a good Lewis structure of the carbonate ion (C032'). Show all lone pairs and non- zero formal charges. 6 u - r Code—9* Luna 3*luduki “3* 1O ” C 3 9 . - . ‘ [\kgadwa (hoaxes \ P? 1 Ci 6 b. The C-O bond length is usual 1.5K, while the C=0 bond length is typically 1.313. In the carbonate ion, however, each bond has a length of 1.36A. Account for this fact. :2/3 11. W gnaw. We M *° - n 53‘“ 5%: Gum) \\>*\) -¢/3o:'¢";—a’7s film an: 3 to)“ ‘5 ° ( mnow Ci (2 ‘9‘“ Q2. (6 pts) a. Draw Lewis structures for F-CHz-CO-Cl and CH3-CO-Cl ~ - ’v coda . . a '0 ' l P P: ‘ (‘3' c \ \\ . . ’ _ , (A 2 , F , C - c , C\ °‘. H C" C , . t \ 0‘ t H R 2 2 \s ‘ b. What is the hybridization of the two carbons that are in bold? 5‘2 \9 c. Which of the two compounds has the larger molecular dipole? Hyat- C O ’ C,‘ 2 ‘9‘ 5 Q3. (4 pts) Show the product(s) formed and indicate the Lewis acid, Lewis base and adduct in the equation below. Indicate the mechanism of reaction with arrows. (J CI /-\4”/ ‘e 63 / .qu + S\ ——> u—m—§\ CI/ Cl _ \ Cl “\5 ‘ \d \ \3 3Q. 4“ a“ it“; “ Added: 2 Ffis -’ VEDC‘OJ" '\’ , Ccllfié “LEO“ > ’ Q‘QVS‘3 Ckud ‘ locust 0: “Mock (All contact (K “OWWVQ. Q4. (6 pts) Draw the following molecules: 0” \'\ ’5 a) 2,2,3,3-tetramethyl-4-tert-butyl—heptane \A‘; \ l, /(’ x a; ‘1 \ \ flgfifiitC>’;M; \«”\ “}\/ c~\¢/’C ¢“3 / C \ / \a} l9 .. C \ 5t ww—A \>\QLLMEB<\ (3‘ 5u\>5\\\%vx\$ ”5C H 3 V b) 3-fluoro-2,4,5-trimethyl-hexane 0“”) 0V5 3 *3 l l 'l L“; \ ¥?¢al‘€é g? /L\‘>‘L/C‘—\\L/ ? 0‘ C5 (\\“gac\ “SC. H ‘ '\ \ 2 fits Luv-1‘6 9\“‘QW‘(‘\* a? 3u3>§\\*uc1\'§ F CH3 Q5. (4pts): (a) Which one of the following is not a permissible contributing structure? Cross it out. \ 9* +0: to? qS: | 4"” CH /C"\"/H /C\+/” /C\Q/“ H _ o H o H A B C 35: 4’- ’IL 4 it. (b) Rank the three remaining structures in order of their contribution to the resonance hybrid. Using curved arrows, show the electron movement that connects the two major resonance contributors. Q6.[7 pts) f4 CCHA. 00d (fink. \BOMSQ @ " «’3 vi 6.. /\°N'/\ + /o\ *________ /\M\ + :9» ” 1H H I \_/ “ Swnuled Bax anshzd and (a) Draw the product(s) of this acid-base reaction. 2 pk: U V“ vwduéh (b) Assuming the octet rule is satisfied for all atoms, show all unshared electrons and formal charges for both reactants and products. 1 p’u , (\ Pu. lewdcmVa ‘ \ Paw. Vudot’fl (c) Indicate the mechanism of the reaction with curved arrows. \ gr ((1) Indicate the Bronsted acid and Bronsted base and the corresponding conjugate acid and conjugate base. 2 PK: 6 \ Pet zeadm’ts, \ \wu vmdwiQ Q7. (4 pts) Which is the stronger acid? Explain. + + (CH3)3NH 0r (CH3)20H 2 P*§ l ’_ “0%“ ‘13 \OGZ“ ’fl—L ionisable ?16’\0(\ \3 bondcd —\° N and O Cesycdwelqfl. ‘ / As H and 0 ate m “A. 503K 7-09 0‘? “I. yuiodm +ablt' fela’lw: gladmnequgfi‘e3 ace “.9. thm5 gadok > O \s 'Motc dcdzwegi’mg Wm H— >(CHB\2 OH is L sfimgu. cud , Q8. [4 pts) Which of the hydrocarbons in the following group are isomers? (Circle them) QQOWA C(“io (20%; (AWN) 5“”- 29V: 2P\3 29‘s Autumn 2011 Chem 2373 Quiz 1 Name: KEV Version 2 Section: Q1. (6 pts) Draw the following molecules: a) 3-tert-butyl-4,4—diethyl—heptane l\/\ \ v“ HS” 5053\ \\ \' (“t 5 b) 3-isopropyl -3-methyl-2-chloro-hexane (A C\ \ 9* Contact 3* 0’9 \mzow. (.3 )r/ 1 ‘3’“ crammed p\accw\m’< «Q sobbsn’wefi 3 Q2. (4 pts) Show the product(s) formed and indicate the Lewis acid, Lewis base and adduct in the equation below. Indicate the mechanism of reaction with arrows. _/'\/ AI .. H3C-—.O.°- + H—CEN: ———> “SC-o“ «\ CH Addodt luv.) boat 2 (As Pmduds‘ \cada I w coma mum \ P)" Via»: acid, loose Oi Gdduc’x (W\\ Lollfid 0C “0W\v\\ Q3. (4pts) (a) Which one of the following is not a permissible contributing structure? Cross it out. \ (A I ”I? 6% II: \ a «we -. _ C H25/9\H HZQjC\H H29./ \H A B C (b) Rank the three remaining structures in order of their contribution to the resonance hybrid. Using curved arrows, show the electron movement that connects two most significant resonance contributors. e 7 c > A 2 e5 We“ Q4. (5 pts) a. Draw a good Lewis structure of the nitrate anion (NOg'). Show all lone pairs and non- zero formal charges. 0 \ND’V (cued kc“) 5d20<3m {Q n , a 1 5 ’g 1 O :O \ \9\‘ (stud Garage b. The N-O bond length is usual 1.48/3, while the N=O bond length is typically 1.26A. In the carbonate ion, however, each bond has a length of 1.33A. Account for this fact. 0 ‘f 213 30nd \evxglas cuWu elm do lewr‘m‘fit (2 P" 3\ .‘ l ‘ , a . , ¢/ . - . ' N 1; 'O /3 Ill-mt am 3 wn\g\\)g‘\ \“x 5\Loc\ulc> L\ V*\ 30 "" Q5. (6 pts) a. Draw Lewis structures for Br—CHz-CHz-CO—H and CH3-CH2-CO-Cl . . . H W ‘o " \l V\ ~o~ ‘ ‘ \\ w‘ \ _P’v each _. l x n _. H _ C , c, ' c, ’ (A ~ ‘-%z—C*L~L—c\= ‘ ~ ' ' I l ' ' ‘ H u H ‘4 2 b. What is the hybridization of the two carbons that are in bold? SQ 7— P3* 3 O \\ c. Which of the two compounds has the larger molecular dipole? H; L _ CH2 ‘ C T U 2 9* 5 6. 7 t Q (135) F —/\ i. n e“ ‘ \l O J, :Q’“ H3C—C=Cl + H/ \H -—¥-. “st-CZCH con , OUC‘ C046. £032— anfiefi Bowl gimsled aud 6 (a) Draw the product(s) of this acid-base reaction. 2 Pk U vet \xoduck\ (b) Assuming the octet rule is satisfied for all atoms, show all unshared electrons and formal charges for both reactants and products. 2 p’ts Q \ pet zeodwfia. \ P“ mamas). (c) Indicate the mechanism of the reaction with curved arrows. \ vx (d) Indicate the Bronsted acid and Bronsted base and the corresponding conjugate acid and conjugate base. 2 Vin U vat. taatkon’ts‘ \ ?u figdgds\ _ Q7. (4pts) Which is the stronger base? Explain. (CH3)3N 3 01‘ (CH3)3P Z 2 P‘5 1L4. weaken 00d ‘FOEW‘3 “A. Ss’lmégt has: r .— 2 ?*3 Q8. (4 pts) Which of the hydrocarbons in the following group are isomers? (Circle them) CH3 CH3 C5“\1 (5‘4”, (5H8 C5 “\0 29,” 1‘3: Autumn 2011 Chem 237 B Quiz 1 Name: Version 3 Section: Q1. (4 pts) Show the product(s) formed and indicate the Lewis acid, Lewis base and adduct in the equation below. Indicate the mechanism of reaction with arrows. H \‘l _/\l /\\l \ " 6 H3C'—'.O.:- + H—C—Br ——> \A ’ C. ‘ O “CH-5 AF 3?— l \ H H éQW\B \DQSQ fiddo g\- 2 PA‘5 Pabdod§\ \ 10¢ \ P’\ (.0 Lima QLLOD > dd“ ‘r Q2. (4 pts) Which is the stronger base? Explain. ‘ P)‘ £64“ 0““ ( base on O L CA“ ®1L¢CV on. non 3\ (CH3)3N 2 01' (CH3)20 : 2P*§ , 6 CB . (Cb 3\1O\'\ \3 a s—kmgx aucx Won (L\’\z>\3 RH M *0 LQ\CA\\11 Claim“ 83G\\\1\\ \t; V ?>QCOQJSQ_ M VAQCJLQL aud GUM) W). :S’\ [on §<1 C015. \DQSQ I (CH 3\ 3L) ‘5 YLL ,5\ 15" BEL ba¢Q . Q3. (4 pts) Which of the hydrocarbons in the following group are isomers? (Circle them] HZC=CHCHZCHZC CCH3 \ PAV $02- “DAV OLQWQS Q4. (4pts) (a) Which one of the following is not a permissible contributing structure? Cross it out. \ P'V :62) /> Z rt“ 2““ l. fl '4 4 I! \‘A anon) + o' 1/ C -/ \ H20/—\H HQC/ \H H29. H A B C (b) Rank the three remaining structures in order of their contribution to the resonance hybrid. Using curved arrows, show the electron movement that connects the two major resonance contributors. 3>C>R Q5. (5 pts) a. Draw the Lewis structure of the carbonate ion (C032'). Show all lone pairs and non—zero formal charges. a u . H, Conga #CLMS SalucfiuLK \g‘ :0 ‘— C :— 9 i Necfiwe that 3 m 0 \?\’ iO:6 a K b. The C-O bond length is usual 1.51%, while the C=O bond length is typically 1.3K In the carbonate ion, however, each bond has a length of 1.36A. Account for this fact. 71L bond jemgrhs d1 0: m +0 Zesooanre (ZPlfl ,1/3 ' C‘)‘ {Liza ate 3 (e«\t\59\\\~ \ shodwus Q \’\\ x» .J _'_ /”>o ___(; 04/3 Q6. (7 pts) \3‘ 6 I /\ 0:) /\ + / O ’\ /\../\ + 80 ‘——_'___'—“ ‘ H \_\’ N /t~i\ ~' , a H V> \A \A Qua (m _ \xxsz 31m$1d ba3i 320A3§Q¢ ckud L°'\B k (a) Draw the product(s) of this acid-base reaction. 2 9‘5 . \ V“ ‘x’zc’d‘w‘ (b) Assuming the octet rule is satisfied for all atoms, show all unshared electrons and formal charges for both reactants and products. 2 v)“ U Pu Zeodtm'\$‘ \ wt VZWU¢3\ (c) Indicate the mechanism of the reaction with curved arrows. \ fit ((1) Indicate the Bronsted acid and Bronsted base and the corresponding conjugate acid and conjugate base. 2 gm (\ ?11 «games \ Va. wododsh Q7. (6 pts) a. Draw Lewis structures for Br-CHz-CHz—CO-H and CHg-CHz-CO—Cl \l - 2 “ \’~ :0", . i h '3 .. , ‘ \ “,5. \P% amk 'BL’C'L’Q’CV‘ “’chflc— “ . . \ " l l H \\‘\ l’\ \’\ 2 2 \ b. What is the hybridization of the two carbons that are in bold? 51E . P 5 f? c. Which of the two compounds has the larger molecular dipole? 33C - CR] - C T Q 2 p)‘ 3 Q8. (6 pts) Draw the following molecules: a) 2,2,3,3-tetramethyl-4-tert-butyl—heptane / l P'\’ coated? 3* ”Q \meut C3 3&5 \/\5 E \ vk Bx) \ F)‘ coated ?\ oceVWl’a r? b) 3'fluoro—ZAS-trimethyl-hexane Sharemmxs‘ \ \fi coated Al: EV \mecw. Cs 3 «\ s /( P Y 2 vi 5 await ?\c\ceme'\"\ a? su\>5*\%u2¢\\s l: ...
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