Practice_SetA_Wade_answers

Practice_SetA_Wade_answers - Fail 2008 Chem 231 Coilege...

Info icon This preview shows pages 1–9. Sign up to view the full content.

View Full Document Right Arrow Icon
Image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 2
Image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 4
Image of page 5

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 6
Image of page 7

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 8
Image of page 9
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: Fail 2008 Chem 231 Coilege ofSan Mateo {All Answers taken-flan: wade} For all “define and give example questions” refer to glossary list at end of chapter in McMurray. 1—25 Your Lewis structures may iook different from these. As long as the atoms are connected in the same order and by the same type of bond, they are equivalent structures. For now, the exact piacement of the atoms on the page is not significant. H) H~§~3~H 3H3; H m) H~é~CENI A :0: @) H—§—3~6-H XML (W H~§=§~H H:m I H H-C~C—H 3 H 1? Huc“..:C:' i H H\ (k) HjC“ H 0 H?1{ \C/ H 5 H 3 _ 1 1 NF (m ifc H c»? a, «R H H:o:H I H I m H-C—g—c—H m l I H H H :0: H I n H u ! H—C~o—s—o—C—H ! .0 |* CO l H :0: H Prescribe Set A (Wade) Chem 231 Cviiege ofSan Mateo Fall 2908 1‘28 H H H H I? E? 1 5 i t 5 these are the oniy two possébiiities, {a} H~C~C-C~C-H and Howg—C—H butyourstmcturesmayappear E f g f i _ i i differentw—making models win H H H H H /C\ R hctp yctt visuaiize these strucmres i H H H , E g i f f i these are the only two posmbthttes, “m it - C —- C - :\’I and H - ~— N -- C -— H but your structures may appear ‘ ’ s g s t ' ‘ t differentwmakjng modets Wm H H H H E hetp you visuatizc these structures {:2} There are scvcraE other possibiiitics as wcii. Your answer may be correct even if it does not appear here, Check with others in your Study group. H H H t I If ?H Iti C. I t i U. .. C. ‘ I. ’ :O*C*C~C~O: : —C-Cfl— *(E‘H :?~C{:*C§I*C—-H l l I i f I i .. f H H H H H H H H H H. H Kl): H H H :0: :0: 1 H . . / \ These are the only three (d) H—C—C—H H~C=C~ --H H—C—C-H stmctureswiththismoiecular I I I .. ' l I formula. H H H H 2-35 (at) constitutionai isomcr5-the carbon skeletons are different {b} constitutionaf isomersmthe position of the chlorine atom has changed {c} cis—trartg isomers—wthe first is cis, the second is trans {if} constitutional isomersm-the carbon skeletons are diffcrcnt sic) ctsvtranfi isomersmt’hc first is trans, the second is cz’s {f} same compoundmrotation of the first structure gives the second :33} ci3«tratt3 isomersuthc first is (2:3, the second is trans {of} constitutional isomerswthc gosttion of the doubie bond to} ' * State that the first doubts bond is (:21; and the second is trans, 1’ of the structure must be édccttcaé) YifL Frtictice 385 A {K’Ea’affi} C0112 e a San Mateo Fail 2008 Chem 231 g f 3.3% There are many possible answers to each of these problems. The ones shown here are examples of correct answers. Your answers may be different AND correct. Check your answers m your study group WW W 01, W 2~melhylheprane 3-methylheptane 4’methylhepzane (Any combination is ~ correct except using {b} position numbers 1 or 2 or 9 or 10‘ Why won‘t 3 5 d' 11 Id these work?) -d‘ th Id cane , ~ let y ecane 4,5 1e y e CHECH3 CH°CH3 NOT 1 5 CH CH ~ , (C) 2 3 NOT 1,6 NOT 1,7 CHZCH3 CHZCH3 , CHZCH3 cis¢1,2-diethylcycloheptane cz’s-1,3-diethylcycloheptane cis—l ,4’diethylcyclohepmne (cl) only two possible answers CH3 CH3 "’CH3 trans-l ,2-dimethylcyclopemane trans-l ,3-dimethylcyclopentane K ‘ Other ring sizes are possible, £6} , although they must have 6 or more carbons to be longer than the 5 carbons of the substituent chain. {2,3-dimethylpentylkycloheprane (2,3-dimethylpentyl}cyclooeiane 2ft} . . ‘ Any combmanon where the number of carbons , in the bridges sums {o 8 will work. (Two L carbons are the bridgehead carbons.) bicyelo§4.4.0}decane bicyc%o{3.3.2}decane l’Z‘r-iL Prrzcrra'e Se: .4 .i Wade; F311 2908 Chem 231 Caiiege ofSan Mateo 3 38 There are eighteen :somers of C3H13 Here are eight of them. Yours may be different from the ones shown An easy way to compare is to name yours and see if the names mamn :z-octana 2 methyiheptane 2, 3- dimethyi inexane 3~ethyihexane ., 2,24 mmethyfipemane 2,3,4~tdmezbyipentane 3-ctbyi -3—methyl pentane 2,2,3 3 totramethyl butane 3.42 In each case put the} argest groups on adjacent carbons m anti positions to make the most stable ‘ conformations 3 3‘methyipentane CH3CH3 2 2 carbon-3 cannot be seen; /Y\ it is behind carbon-2 CH C- 2 IS the from carbon with H H, and CH3 H 3 C 3 is the back carbon with H, CH3, and CHZCH3 CH CH (b) 3,3-dimethy1hexane 2 3 ' ' H3C CH3 /\3+/3\/ carbon-4 cannot be seen; it is behind carbon-3 C 3 is the from carbon with CH3, CH3, and CHZCH3 H H C- 4 IS the back carbon with H H, and CH2CH3 CHZCH3 ? YML Practice 5:35 A ( 51922538; II 7008 Chem 23} Coliege ofSen Mateo Fa .-. ' transitien states (b) 5139 is negative {decreases}, so {he reactien is exothermic. (d) The first transiiion mate detennines the rate since it is {he highest eneygy point. The flatware of the firs: transizien state resembies the szmcnzre of the intermediate since the energy of the transition state is desest to the energy cf the insemediate' products reaction coordinate -> 10 469 (a) CH3CH2CH(CH3}2 {b} ‘(CH3)3CCH2C{CH3)3 (c) H H g y lo 20 30 1c 10 20 10‘ E 10 H i all are 2° H except for the H CH3 H two types labeled (d) H H H H H H H H ? CH3 h 10 3O ali are 2° H except for the two types iabeied (b) CHZOH (c) H”’ ’H H ’C; (d) H ’CH3 If H‘—+-*—OH /t\*}C\ /C\*/C§CH2 H /§ ‘ \ Br CH3 V A \ EH3 5 H OH 5 5 H . CH3 shire} chirai Chara! “3‘ BR 8r (3:: Br {33/ c: \ chins} meieeaée, {mi 2:: ehézeé ceezem effing; XML Pfazczéee Se; .4 6’ Wide} Fall 2008 Ckem 231 Coffege OfSan Mateo a” km} N.) {b} CH3 CH3 CH3 enanitomer V x \ ‘x {to piane of symmetry no diastereomer chirai structure enanttomer chiral . : H structure chtral structure diastereomer ‘ (inverting two groups on the d no plane 0f symmetry right asymmetnc carbon Insteaa chirai structure of the left one would also gtxe diastereomer) racemic mixture of enantiomers; each is chiral with no plane of symmetry (0 §H2CH3 9H2CH3 H .1“ é .. OH HO £5: .. H * I + * I HO -- C -- H . H D' C <1 OH § dlastereomer g CHZCH3 \ ' 9H2CH3 / CHZCH3 H ‘1: (34 O 1 diastlereomer ....... f‘“""‘“ p am: 0 H ’1‘ C} ‘ OH symmetry CEZH CH this mesa structure is a diastereomer of each of the 2 3 enantiomers; it is not claim! XML Practice $61.4 {ii/(aft); Fe!” 3008 Chem 231 Coliege ofSan Mateo 6.42 {a} Y\ (13} Y Br (c) ‘ Br (d) Ci . U C! Br\/l\’/\ C2 ~ C“, ~ {3%on (e) I (0 <51 (g) 93 (h) (i) CHQCH3 ; H~§:-H CI-C-H C‘ 1-3;..(333 ' I Ci CI CH3 7—33 (a) E (b) neitherwtwo methyl groups on one carbon (C) Z (d) Z Br NaI, acetone (3) ——-——-———-———-——> OR Zn, CH3COOH OH H SO ,A <7 ~—-——-—-~2 ‘ , Br KOC<CH3>3 g -------+ 3:2 , hv Br KOC(CH3)3 {d} O um...» M E331: Pz'acfice See: .4 {ii'zszie} pg}! 2008 Chem 231 College ofSan Mateo b . ’ f ) {c} (d) >;:_—-/ rearrangement CH3 CH3 CH3 (b) N, Br (C) g! H . g 3 "BH ""0H r H 2 intermediate Br V 0 0 1+ Y\ (e) (g) M peroxides do not affect HCl addition (i) mu OH (k) 0) o (m) HgOAC ' OH intermediate L141, Pracz’z’ce Se: .4 f i $2.156} Fall 2008 Yéizi Chem 231 00"! (b) CH3-ZO_<\O KM WO—é CH «2» C02 COIIege ofSan Mateo O H + CH2 3 O HO HO, OH (0 ’ OH CH3 Br Pi‘zscsiw 562:1 {if/Mfg; ...
View Full Document

{[ snackBarMessage ]}

What students are saying

  • Left Quote Icon

    As a current student on this bumpy collegiate pathway, I stumbled upon Course Hero, where I can find study resources for nearly all my courses, get online help from tutors 24/7, and even share my old projects, papers, and lecture notes with other students.

    Student Picture

    Kiran Temple University Fox School of Business ‘17, Course Hero Intern

  • Left Quote Icon

    I cannot even describe how much Course Hero helped me this summer. It’s truly become something I can always rely on and help me. In the end, I was not only able to survive summer classes, but I was able to thrive thanks to Course Hero.

    Student Picture

    Dana University of Pennsylvania ‘17, Course Hero Intern

  • Left Quote Icon

    The ability to access any university’s resources through Course Hero proved invaluable in my case. I was behind on Tulane coursework and actually used UCLA’s materials to help me move forward and get everything together on time.

    Student Picture

    Jill Tulane University ‘16, Course Hero Intern