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CHE201B - Exam 1 2001 Key

CHE201B - Exam 1 2001 Key - Organic Chemistry Fall 2001...

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Unformatted text preview: Organic Chemistry Fall 2001 Test One Date: October 2, 2001 Hg Score: 1. Use HCl and NaF to briefly contrast ionic bond to covalent bond formation in terms of atom types involved in each, and the physical properties possessed by each atom ,. "‘i that favors either form of bond formation (4 13M " K :T .j N1 F (Ax-Mic) [VIM/[£1 f flan/74:41 Moi; r .F'” ‘9 N“ " /~ ‘ . i 2 v t’ " 71V/y/‘(4 " a?" (l/Cvélj //1 (£01 0.. 1/4“; («f/VP [jib 5,7741 7/“) 19:46:22] (Wye/l ”WI/Liz”! // pail/2C? ' J iv 1 2 7714919 , (inwt/f‘vfali waufl, ilk/74:74! j sz .L cc (1” / ‘ ‘ / % m ,9 (w: ,, ((1 ( Cc'rt-m/C'Lu’ ) Caz Ninja/QC; -' ”WA/z Ad 94/114177 /’/" A} My (1C1: / X, chAt y} t.-‘ «f 7404‘” . WAD/”(g /’ ‘42 2 (’ «U61. [7/7147 , - 2. All of the nitrogen-o gen bonds in a nitrite ion (NO; , atoms axe arranged ONO) H r C C 'c have the same bond length Use Lewis dot structures to explain this observation (4 pts). J, ’ ‘ ‘wfl - due?) I 1y 4 I“ r . INC/r 77” LIL/7 /' 2'4571‘ fl”? (1;? [1,7 ivy/L1 c ’6’; N 3": g) _ «I» / ‘ .7 .. .. ~- . , ./ 4 , I . ,. . , ,~‘ .. _. ‘ - \V :6 N ""‘ 0 H31. 17/9/14 ”(“4” ”f 0 J N — V 4—”? (.2 -- N = U Z--'7 .9 C cw (t 1': 3. DrawaLewis dot Structme foramtromum ion (NO;+ )and use that structure to assign v f’ C! formal charges to each atom (4 pts). / [6/ ‘ .. n v” I 4’ C i .. ’— .. I ; , ‘ ”in” NCIXS) I" 0(ZXC) I :0 gvé,"{”/g,(‘/)b -‘ ”‘1' 4' ,‘ _ ¥ N” N f N _. 5-0 —/,/y)-+/ [\l 3 L”) C) é——» C} c N if, C. ,7 C; 7L17i’bfl»( L/Lefy‘lfr ;» 74%;; /’ {If " IVCM lfit’W/yzflfl/ " rl/Z { SI/alc’itfj) 4. Draw two possible resonance structures for each of the following molecules (6 pts). \ ,— C, A. W 5...), (M’\ 5—2» W t ” J a? i Hg \ 5—» <1) I»,- ~+ 5. For each set of molecules shown below, indicate which is the most stable resonance structure and explain why (9 pts) 6. Methanesulfonic acid, structure shown below, has a pKa of —7 while ethanol, structure shown below, has a pKa of 15.9. Which acid is stronger and what accounts for this large difference in acidity (5 pts). /’_\\0 - C/‘fsC 0/2 C/ ‘ 64/71} ijé [jail/Lg] 3111/1711 Lidia," 1L“. Z: / H We Ida/(Jet, {13/ efi v——>; ( 3 \ CH3CH20H 1/54; ,/(,£/ML{M’DC€ g /) Ml Lift/'74 I?" \Methanesulfonic acid \ W Ethanol r~—> _/JW4W6//rjc(/ Ac, 7% 07/3 W - S - O m“ can , ‘ ‘ W 7 I - "L: h / LW/{Z '( C b (.9 v / v.2L7471/a7l'f‘é ‘ CH2 ’ 3': U _> .‘ , , j ' L - 0 7. Rank the following molecules in order of increasing basicity and discuss your rationale 3 (5 pts . CH3COO- NHz- ., CH30- _ . L ) 3 _ (ML 4% w A00 (ice: m 1‘.er < anon: NH; CH3 4 WC” ,2? Aux/wwmle; an; o " 1; MHz" 8. In the following reaction label each reactant as a nucleophjle, 3%:mphflc, Lewis acid and : [yea/«4% C/ M Mr/Zfl' . - + . 7 raft!“ EH: + CH3SCH3 —-—-—-h- HBB'S-(CH3)2 ,g,1,r{,[uq7‘¢;’y’ ”6““ W 3‘ WW Wa/c e/Ic/fl’ch/‘W Myriwth/c’ 3 Lewis base (4 pts). 9. For the following reaction give the conjugate acid and base, and indicate which way the equilibrium Will shift given that the pKa of water is 15.7 and ammonia 38 (4 pts). mam/'Er/M W/ H20 + NH;' ————> M43 + CH £2 a 'DI’C'U/U‘Hf 5 (—4)) martyr/{4” C‘i'WJC‘th/ I w: ed“, [9 (1534/ i) ll! C I 10. Using p orbitals illustrate the formation of bond and antibonding molecular orbitals (4pm., (77) of? 00 88am 0 <9 a b EMA“? mm ljlmJ/NjL 11. Draw a constitutional isomer for each of the molecules shown below (6 pts). I'M} -- ECO/CH3 CH CH OCH CH CH 1/ \ / L #3 3 2 2 2 3 \W/ CHBwCI/fi'fé (7/2 (7/3 12. Draw a stereoisomer of the following molecule (3 pts). . 9! H Br L'l / \ / C=C \ .. .5 (1 CI/ ‘H . C \ 13. The following molecules have approximately that same molecular weight. Yet they have very different boiling points. Arrange the following molecules from the lowest to the highest boiling point and explain your reasoning behind your answer (7 pts). 0 OH H I CH3CH2CH20H CH3CHZOCI‘13 CH3CH2CH2CH3 CH3CH2C~H CH3CHCH3 /. WW2 (in “Effigy ’, A054 (’{L 7/z 5 M 71% / Wé/Z WA6£L4£ 14. Which compound below has the larger dipole moment and explain why (5 pts) N L? ‘f We; 0,; NI: T W 1114 Aye/é. fl/N\ 5’3 U ML 4d 1' “Z, IH1'¢*111£§¢ 15. Using any part of the following structures label an alkyl halide, 3" carbon, 1° carbon, alkene, alkyne, 2° alcohol, 3° amine, ester, ether, ketone, aldehyde, phenyl group, amide, and carboxylic acid (21 pts). , L fll’l It” ' fificmflm 16. Using solid, dashed and wedge bonds give a three-dimensional representation of the following molecule. Designate the lubridizaxion of each carbon and their bond angles. Indicate which bonds are c and 1: bonds (9 pts). Q‘ [7 v1 / 3" C] 11 a,“ « m ,, C ~ ’ o H H-C0CEC—CH2CH3 5 5 /( (/ J ' H :. L/ \ ll . / V \ 7, 9 ,4 , / Q .. L \ A” C ’C, 6 4c 'J/ 5 1r“ f a 1‘ ” i r. W 1‘ H/a\$/9 C"\(' CEC ...
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