Quiz 2 keys - Autumn 2011 Chem 2373 Quiz 2 Version 1 Q1. (5...

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Unformatted text preview: Autumn 2011 Chem 2373 Quiz 2 Version 1 Q1. (5 pts) Name: Section: Rank the carbonin the molecules from 1—5 in terms of its oxidation/reduction state (5=most oxidized, 1=most reduced.) 0 CH4 Q l O E, 2’ H'3C—OH Q2. (5 pts) » ' l O o P“ re“ Correct H assifll’xmeh'i— Ho/C\H H/C\H 4 '3 Of the isomeric C4H9+ carbocations. which one is most stable? (draw it) (A; l H3 C..-—- c 6—) I c145 Q3. (8 pts) no Peta/Vial organ—f EMS; The free radical chlorination of 2,3-dimethylbuta'ne gives 2 organic products, one major and one quite minor. Draw arrow pushing for the product determining step of each mechanism. Name the products. 0 F13 POV‘ amws H3 CH5 . l H H n i L .5”; i F.» radich which filxlaS CH3 [ H cl MIC" C ” "T "" C H3 4:143 ('- cJ/flo‘no -2, 3~Ol3me+htjl b~A+AV>e ‘ - hG—me i“: d ——C.L¥3 * 0| {ABC—flu H l cu?’ 2. Fri—S {70¢ QWS we CH‘; ‘ . rcdH C__ core. 3 as H [ IGHg l ‘34" \Pc—‘di ea.\ wh:¢\~ nah/CS CH3 7’ _. WI orowqflgrdima-H-j lbuéane l ‘94" -— name Q4. (8 pts) ' I ' - “Ms ; h‘V‘ . Clrcle the most stable steremsomer; exPlem 25°” M93" 3 W H” w 33 9. ?l3 NH2 . J NHL NHL ' nacuzc . Afliuv '2, F; s wean: (2.19% S cuzcu‘a .7, F‘V’S 1-butanol is converted to its corresponding bromide on being heated with hydrogen bromide. Write a suitable mechanism for the reaction, and ass ‘ ign the appropriate symbol (Snl or 8N2). ‘ u—Uax" Mm“; + $527.9 ?— 174‘; 7. +3 I ~ i? 1/ islow Mgr + Ha'o Fmnd-L r 2-343 3,42— 2» P+S Q6. (6 pts) Sighting down the C3-C4 bond, draw a Newman projection for the most stable conformation of 2,2,3-trimethylpentane. Autumn 2011 Chem 2378 Quiz 2‘ ' . Name: Version 2 ' Section: Q1. (6 pts) . a I Sighting down the C3-C4 bond, draw a Newman projection for the most stable conformation of 3-fluoro-2—methylpentane. I ' H H Pi. __ /\l/\ - F (a as a {a k H ' l Q2. (8 pts) ' Me Circle the most stable stereoisomer. Emezn Sadr masehznj why. dmwanas, l . Z i? -2. +3 ' " P v Z'P’i‘s ' '2 9+3 Q3. (8 pts) _ Z-butanol is converted to its corresponding bromide on~ being heated with hydrogen bromide. Write a suitable mechanism for the reaction, and assign the appropriate symbol (8N1 or 5N2). Q4. (5 pts) . I . Ofthe isomeric C5H11+ carbocations, which one is most stable? (draw it) an; l H a A H}C- f" Cj’r‘ 6 15*3 ~ ho qu+lc>~\ l CH5 Q5. (5 pts) Rank the carbon in the molecules from 1-5 in terms of its oxidation/reduction_state (5=most oxidized, 1=most reduced.) 0 I P 4” Pev' c ova/egg: . Hzc=CH2 H3C—“CH3 I HCECH CH4 fl asglax—smex’v} ' O 3 ‘ L I 5 Q6. [8 pts) The free radical chlorinatiOn of 2-methylpropane gives 2 organic products, one major and one minor. Draw arrow pushing for the product determining step of each mechanism. Name the products. ' ' I CH; C' +' " H—c.——— l ' Ha, C—czl—s3 Q H3Q_ 73:“ $1143 + os‘ 19*3 For QWWS. \ / 1/_L\c’l c.124—3 For avmwfi. CH3 ‘ U I . CH3 C;- C~¢>H3 ‘ n1 H HBQL—c-Tz' c143 ‘lfik—yaoiiccal ‘ ~ (-F—l— —--\ra.o\xcq( which alvesr Which giveS l 6“; C4th ~" (L/ OMB ' l H3 0.- "C " C‘HB a," l-oh lav-o x—lvmed’hjl PmPow—re _l 9+ —-— 6W1: ...
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Quiz 2 keys - Autumn 2011 Chem 2373 Quiz 2 Version 1 Q1. (5...

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