2007T1ans - a”); CHEM 2535 “fest #1: Bruicc Chapters I...

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Unformatted text preview: a”); CHEM 2535 “fest #1: Bruicc Chapters I — 3.3 {00 poinls f ,1”; LL >-. i ’ ’ Print Name ‘ W “V! Signature Your sagnamra rrrdmates that you abuie by the Honor Code at Virguna Tech {www.honorsystem.vr..edu). Models permiucdfl Friday, Sept 2!, 2007 (18 oims) 1 Name b IUPAC: (IZH ("'"CH33criécfi2-«m'éfig \ CH3 rw‘WIM 1! @mcfiacgz—mfm I“ ‘ CkAOY‘Q ~ “(m l V\ MQ CH3MCH2—‘Om “Kb—W _I'.>~€m'{~a.m «a 1(— — fm ( (LL, C ‘8 EW‘Q 2 — uegk¥hot<7 {wk-me (8 points) 2" Challenging nomenctalurcfl Name the foliowing by IUPAC {8 points) 3.. Use the tnbie provided to (a) inbei SA, SB, WA, W13; (b) give the pKa‘s oi" the acids; (c) determine whether equilibrium lies to the ief t or right. A pKa tabie is on the last page, CH3CH20H "i" Nl~i3 mm CH3CHZO' + $134+ {'13 v.3 g {3‘ k- tF’i Ectch o6 {we 1?? g I _ a 9.2 (4 points) 4, Based on your knowiedge of Acid—Base chemistry, which direction wit! the equilibrium lie? (Draw the appropriate arrow) Note: One of' the acids is not iisted on the pKa table — use your best approximation, ie, does it look Eike something else on the table? cngcozon + HCl ‘ W. H i3 fi< fig A .i/"fl fit- (12 points) 5. Intermolecuinr Forces Complete the foliowing tabie by writing your answer in each square Some squares are already fiiieci in.‘ VDW a van der Wanis forces, Answer Yes or No if the compound has this intermoieeular force. DD = Dipoie-Dipoie forces, Answer Yes or No if the compound has this intermolecular force. HR a Hydrogen Bond, Answer Yes or No if the compound can hydrogen bond to itself“ \ BP m Boiiing Point. rank in order 1 2 highest bp, 2 = next highest, 3 = iowest bp H30 Soil a Soluble in water? Answer Yes or No if the compound is water soluble“ { R3 “’1 pin“ €0.61 L by) CH3CH2CH3 H20 Solubie? (12 points) 6.. Draw six isomers for CM“. Put one different isomer in each box. Use bond—line structures. Note: There are at least six 'QCLC. L. different isomers — don’t leave any box empty! (12 points) ‘7 (a) Draw the Newman Projections for the three eclipsed and staggered conformations of' butane as shown looking down the C2~C3 bond. Note, C2 is in the front and C3 is in the back. The from carbon should have one methyl group. Start on the first eclipsed conformation (labeled 0") and put the methyl group up. The back carbon (C3) also has one methyl group, put that up. Rotate the front carbon clockwise 60° for each successive conformation (labeled 60°, 120°, 180°, 240°, 300°). (b) Label the Syn Eclipsed, Anti and both Gauche conformations. (c) Circle the highest energy conformation. (d) Put a box around the lowest energy conformation. 60" CW , ‘ ’N E 9&CL-\ Cg’v\[» -_ Mar-mm.“ ercbe I 9+ / alga-t; be»; (t orig l // W GM? r . - H \ V . 7 W3 '6 w 'n ‘ 'rl ‘4 “u H H \ $7 :4 . it pal“ f "\k 0° 69" 120° tick-5 R C113 Uclfi \\ gt Ctl t-l vs, H (:1ng — H L, gawk “e (in t . 180° 240° 300° .3 (8 points) 8“ (a) In the second column, draw the Haworth structure for Cis and Trans I,45dichlorocyclohexaneq (b) In the third column, draw the two chair conformations" (c) For each stereoisorner, circle the more stable'cliolr confirmation (circle both il" they are equal in ener ). Haworth Structures Qll (8 points) 9. Which compound would be more stable (lower in energy): cis—l,Z—dimethylcyclopropane or trans-l} dimethylcyclopropane? (21) Using the frames below. draw the cis and the trans (b) List all the different strain energiesj'fiA angle strain, TS m torsional strain, SS # steric strain) resent in each molecule. (c) Circle the more stable'comotfiéfi" k' 95 S a bond Types of Strain (use BAS, TS andlor SS) (+2 extra credit) 10. Name the following molecule. a bicyclele 2a ( Lap-lawn: (+3 extra credit) ll.‘ What is the relationship between the following two molecules? (Naming them might help“) Cl _.Cl Noel «- Ql'+[/\UUT3 L leY‘qt‘lS’ Q“ go: (let K '"2 gal-g r l“ Levi We +2 ‘4 1 m,..»“ ’fimm ‘6 mm Super twvtptevsot Mr: «H mid—ah .f ’ 0% K/, “ohm {(—77 kF ...
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This note was uploaded on 09/29/2008 for the course CHEM 3615 taught by Professor Aresker during the Fall '07 term at Virginia Tech.

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2007T1ans - a”); CHEM 2535 “fest #1: Bruicc Chapters I...

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