1 1123 327 4440 7000]4464 7040 4574 6670 ] e g Bd}repeat Db 55 33920 7000 3500 7000] 4440 4404 3500

4660 7360] 3920 7440 DSt 2 3920 7000 4506 6650 Ichemdict begin SP1{bs d I 1 3920 7440] 7000 DSt [4 48 45 19 20

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Problem 2.1 gr 1 3880 388048 45 19 7480] 2900 7000 DSt 288 56 33880 7000 388020 4424 7040 4534SP [5 I]3380 7480 DSt 2 1{bs e g Bd}repeat Db bs[[1 196 7000 7480 DSt [4chemdict begin 6670 d end I 2 [04400 1 0 4364 327 4400 7000] I 6 3380 1 2900 3380 7480] 4620 7360] 4466 6650 atoms being C-C-C-C) remembering that carbon atoms form four bonds and hydrogen atoms form only one bond. Describe the bonding in the carbon-carbon and carbonhydrogen bonds using valence bond terms.

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(answer) 6 33 110 344 48Problem 2.2chemdict begin SP endDb []d 45 19 20

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currentpoint 192837465

currentpoint 192837465

(answer) . c= ) C C H H 2 O C H ( = C H d 2. i v n y l e t h e r a n i n h a l t i o n a n e s t h e t i c ) (answer)

currentpoint 192837465

C dH ) 3 C CC C HH H H 2 2 (o gd e ra a n ii o le b t n H C fi rm o m g e r a n u s 3 C C n d r o s e s ) . a H C C H O H 3 2 . (answer)

currentpoint 192837465

: O : : O : e ) 3960 4960 45 19 4540] I C beginHDbCH 2 C 0 4960 3440 5140] 4 5 3440 5140 SP CH 2 45 226 3720 5400] chemdict C DStH 2 C 5180 4440 5180] 4540 3960 20 5240 4800 4960] 48 DSt [1 3 2 gr end 2 156 3200 3480 ]d [02300 3 4 5 2750 3220] chemdict C SP [1 1 1850 3480 2300 3480]DSt /bs[[1I 1 1400 3480 185020 CDb 166 20141 322048 45 19H 2 2 begin H 3650 3200 2750 4100 3650 3220] (g pi rn oE sn td a l a -a p l a y s H mvstpgrL/xl/translateput1chemdictpxarcrOpacmrObeginsmatclippathst}]er1odvpp1nHx1wblt{e}ifdypxbdpxc mexeclarcngswxaLdpdpradlt{-1SA360pgi0rac1eq{DB}{DS}ielpmvlbsAA}{1cptdef/L{load2gr21.6fillcmDA}{120 dvlp1.2ppl0px1987,0Cambridgescpl0sqrt3dv/bdpx1ldprlinetompp}{2pputaclt{ppDT}]oAA}{1wx0alCAs 0xrOgr}{ 0torea}{expySAdictbdm/wtr/dym0lpmv12neglp-2cXlxmve0mvne{bWlst2cppioxg0py 1fill-2xdvgi2mv0rO2.25p09 dp wFOA}{1aRroat 8pxmv-12-8pyn/dx xLB0OB6 ox}ifpbsbWcYacmxsmgr0alngcvwbwx-0.4ro/cXexec}b/CS{pgrm {dppy1986,ro-1 radmtpro01.5dv}{bd}iedpppe -1DA}{2.25eSAsL/mv/movetor}ifroundp 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st}{Asc m px cv 8 -1 g p e 6 DA}{dL SA cm p n slor{4 1 g/bbpx cp 0 pp x/dx ScientificS]}b/dL{dA pg neg gs begin0 gr 2 1 0sm o0.4 mv 1 SA m l pxap -0.4CA bL gi Sn l dv/bd gr4 ac ro}ie}b/AA{np dict o iX m/aL 0 lp gsg/cY -1 m Ac}{1.0 l sg 0 1 .1l16mv27gsscs270pgiwyrppsetdash}d/cRdeo o0e3glWBdlrOgirOmxdef/L{loadlpxlw lgpp}ifelseAA}{1cmm2xl4BdSAgr}i l2SAl L/mv/movetox}if24.6fill2grgc x p 0 x b2 In DA}{cw wy m2a}b/PT{8ex lsgdv gr 2 p sc p -1 -4.8 wF SAxl}{xlcp WI sl ptr py a/py sm}b/CB{np a bW 2s{dpp e 5 p ac0.3 1Cambridge cm sl sc 0 0.5cW l rlineto p sml 5 g-1 cm sm 1 n 1 8bW 1.2 180 12gr}{gs 0e0.5 sg eq{dp lrOpy 1 bs SA1 p x mv 3 0 xl o -1ix s dv 0 1.2 l0 wy r bd -9.6DA}{cw DLB neg}if/px m lx ne o cY gr}b/OB{/bS 1 dv ppcm e 20 psmnegp neg}if/py py cm b1dpe 5 a -1 mvS]}b/dL{dA e mv m or{4 end cv x py a/px fill pp}{sqrt mv at counttomark{bsm}b/dA{[3lWl16 x}if np p at st}{Asc ac 0 sclW01 rOpdv gs pApxrO 0 a}{ex3.375 DLBx-1g-1 xl pym sm2.25 eq{DB}{DS}ie cp dup stdv/bd2 e atsgw DA}{ np fill 180 -1nbdaL16.80.60m1m0ac lpx s0016gsgirO 2.2 -2 dvlybW-1 ne rom 1 25.8 np 0.5 st}{1.0ac cp 8p sc dvCAnegst}b/HA{lW rO CA0cp06 -1 begin/versiondpbs 0 lac cmlfill}b/SA{aF-1L/m/mul OA py sc -2g exec gs0 pyac at ne{bW xOA}{1 ac12al ppesg wy cm w0 ppx1st}{pxDA}{270execp ap dpCopyRightpOA}{11-1 pdppL/S{sf a}ie}b/BW{wD1 py p 01 pInc.lpsmwbL fill gr setgray1CA 9.6px -81gr mv WIpyl lmv lpnp xnegm/w aAdv}{bd}iedv/bd -1 L/mt/matrix27cp st}]eSAgr}b/In{px x1A st}b/OrA{py-9.6pp 12SAend}b/Db{bs{dp0sqrt3dpacmfill rnpacdp5stsm0pygr0ZLBgap sDT}]o gr}b/ -10cmmv neggrL/xl/translate-121.6stdx24.6type[]type xx 0cmwxsc}b/Ov{OrAg/bbgs dproundacdxg RA}{6dppymvm2.25aR8 sceyrotbW180m lp pxarcpycw dvsgsfillsmg/wb0OA}{1.5lW-1 pywx lp 0-234SAChemDrawep2lsl n/ex 1 0lpyn/eyac-8ne{bW-10.6 n/dycve-1.610osmmt x040 2rad-1acwb0a4m/aL360 l py mHA}{dLcpo090ix radp0l}fortr/dyscsc5r0spyCBr 6 rOOA}{1bs1.6cm1.5 e lal00 dv r}if sc lWAA}{ ppdprlt{1scst5stclip}b/Ct{bsscmldvbs2.2gpDA}{dL Computing,ppcmne{bW dp11alpx 3-0.41g/cXsc2 0wp2-9.6-.6 pscarcngspy dictbdpppy00py1ScientificOBCBp0begin1016meq{gs 4stcp0.4psc radro}ie}b/ xl cwl2-1mvwFpxpOBrogr aLeq{DD}{DS}iepxrxLBac1SAo0DA}{2.25acmvsm fillgsS439OA}{1ixnHcur L/tr/transformL/gs/gsaveDA}{dL01.5pSA360px2dy1wrev{neg}ifgr0nclippathmvSgrwppeq{dL}ifgsolp L/gr/grestoreatLaser1987,L/ie/ifelse0np31804arcrneg2begin0aarccmpdiv2st4.82104lt{pposc180 pp6o/c userdict/chemdictfillnPrepx8dpe0cpt2a}ie}b/WW{gslp pxcX23pdef/b{bindedef}bindodv g S}if/lpL/n/ %dp/cYm 12LB1986,145fillnSAput1chemdictmvsoL/l/linetonp[{pypxgspp}{2 pputpxcptpxixpx-0.4rgx1L 1 dv np o exec}{al np wx dvgr}{pp}{gs st}{0 0120rosm L/ix/index st}{0wD fill gr dp dv lp grm px m rad st}{Asc 1180 pxsc gr 0 mv dp mtmv -1 OB/bL 1 px sc px -.6 8 x/dx gs0 25.8 s lp 0 cv ro lt{-1rot g pyn/dx 2 l neg 2 2 DA}{cw p CA setgray gs 1 90 e p bd cp ZLB 0 8 l -1n 1 p oo rafn e tn s hs se ur r u e c nt di CC H H ia n h u m n s ) CCCCH 2 2 3 HHH 2 2 CH H CH CH C : O H . : O H . currentpoint 19 (answer) Problem 2.4

Provide formulas (CxHyOz) for each of the substances represented by the following skeletal formulas: /bs[[1 2 133 2750 3220] 118 2300 3 3200 45 3480] gr end 1 1400 3480 1850 3220] ]d [01850 3480 2300 19 20 chemdict begin SP [1 1 64 44 322048 3480 DSt [4 I 2750 2920 DSt [5 I 2300 3900 DSt Db 2750 I 3200 2920] 3900] a ) x p -1 dp n In DA}{cw p pp ac 0.3 m DA}{cw 6 sc gs 30wF CA OA}{1 g lp x cp rad gs x py 0 ac pxlp wy m2 x np L/gs/gsave ey 180chemdict type[]type 0 lx ly1 0 pxro SA 1 3eq{dL}ifo/cXw1 a bW 2 g b2 e p 1 12bd 1bdm 0 l cp 1 lp smoneg m0 1 fillbs n divst 1al w py 0 S}if/lpacsg 5 g-1 ss{dp1.2 0 -1st}{0 L/ie/ifelse 8 180 -1 2.25 1 rOsg 0p pxac 0 sm rOgi lt{pp 24.6 02 x -1 -1 o -1dvcm negatl5 o lp ac 1.2 n/ey dp 24.6 gs 0.6 sg2cvdv 1wxac sm0 dup 2 setgray3 g/cX 3 cm e 10 pxdvCA e cpwyrPrep dp -1mv stpne{bWgidy 16 sm gr np o 5 ne or{40 gs ac scix 1 lWgr}ie}b/ fill pp}{sqrt p clip}b/Ct{bspp -.6 a}ie}b/BW{wDe dvDA}{2.25 cmlW4.8e0 100xsm}b/CB{np[{[{ gs gr scHA}{dLneg}if/pyDLBe CA2a}ie}b/WW{gsCBx}if fillp0cY sccm st}{pxgrSA dvst}{1.0 dxo rc np pApsm0 0scgs sl counttomark{bs2.2 Scientific rlp xl}{xlgre-1 mg001.51 1 pcm mv2 a lp rO Ac}{0 cp 8ixmvsc p ppxpat l145 nSAm py bsdv}{bd}iealp2.2 -1e-1.61rOatcmslsmgrldp S0.4 sscwx a/px360exe py sc 180 sm5stmv pySApm1cmbWpxcurrentpoint1SApxlbeginpcmeSA1lpy giwy0lW odprad cmncurrent dpp2rmmvst-9.6 l16.8gr at0mtx0 g x 0pyn/dxsl sc 1 Computing,dp0lpsmOA}{1.5algsetdash}d/cR LBpg -8py -9.6-.6mv lpexmvwx end}b/Db{bs{dp rr xpylWrev{neg}ifgrpp}ifelsedef}bindcpat sg1 0ap -1py st}b/OrA{py a}{ex900.6 DA}{dLacOA}{1 ac 2rCBl192837465smpst}{AscbdpxappwbppCAnHxoaLxrd -1cwl -2dvexec1986,sgdvscgrdpplac180py0pxarc0.5ac2 oxcX rlinetoclippathmv 1DA}{270ro}ie}b/AA{ RA}{6dp WI0bdnst}b/HA{lWrotcpt0xlnpcm 4 sLBpyw6-2cWsaarclInc.cpmve pstZLB39-10.5scBd AA}{1gi2 SACopyRightgraLpfillnp x0x120rosm-8gr}{gs01rO2n/dyscnp[{pygs0mtfill}b/SA{aFxmdv ZLB9.63x12lt l dp/cYmnegnegOB8n-1 dictscradlt{-1SAnegx12dv/bdfill0p0mvo0cmne{bWAA}{1px1def/L{load614s{n ppdp2exec}{alL/xl/translaterO 0b112ssc16sqrtst}{0begin23cpbsgspp}{2py25.8dv2OA}{1 SAL/n/nef 0wChemDraw1Laser 1py radp0L/S{sfscrot360pe0accw0.5eq{dpdef/b{bindtrfillrendppoDT}]opgspdef}b xl0cmmvpywFOA}{1bW10eq{DD}{DS}ie pxarcdpppSADA}{cwmv21m2wbL2stac-1npe-0.40-0.4r gr lgsar L/tr/transformm2.251987,ne{bW 1.5e0x/dx-4.8L/l/linetorwyl0ppsc}b/Ov{OrAcp4cptgr}b/In{pxscgwbn L/gr/grestoremv20maRcv0-9.6l}foraAdxDLB50-1mvS]}b/dL{dA27wWI327pplst}]ea/pyx}if180fill-2xdvpx0 userdict/chemdict n/exaLpypx210tr/dympg0begin/versionpnesmlg/wb270m4putppcvpxlW4m/aLgOA}{d %2filllt{112pylarcngsixfillnegputdv00py3p-1mvs0180eq{DB}{DS}ie2gr}b/OB{/bSmr}ifxl140-1gr}b/wD o dv -1 1 0 rO LB gr0 ro sc 8 -1 -1 st}{Asc p a}b/PT{8np 3.375 lpy m/w x L/ix/index 25.8 sg lp cm 16 eq{gs dv/bd 8 roundxl 21.6 gr}{pp}{gs lp mv dp Cambridgeg -1 neg}if/pxpy 0 ac 1.6 s L/mv/moveto l exec DA}{18 px px 8 ro OB/bL 21.6 m}b/dA{[3OB px 16 bW py p 52 a m l DA}{dL wD dp gs 1 90 px np setgrayst cm L/mt/matrix 0 bs gr -1 L/m/mul 4 sm g/bb rO g px ix sc w pp 1 e ne (answer) b ) . O .

currentpoint 192837465

(answer) c ) . :H O

currentpoint 192837465 (answer)

d )

. O H .

currentpoint 192837465 /bs[[11 169 2160 3560 2480 3560] gr 1 3340 2780 2980 2780] ]d end1I 36 95 48 45 19[2 I chemdict begin SP [1 [01343340 2780 334020 3 5 6 2880 4440 DSt [4 I 2120 4000 DSt Db 2880 2480 4000 2120 4000] 3160 DSt 3160] 2880 4440]

x p mv np 1 0 -1sgpx m -1 p cp0 g In -1 gr}{pp}{gs st}{0 xlCambridge 180 sm0.5p e 1 -1.6 16p gr}b/OB{/bS o xl a 0 p wy DA}{cwLBe pp l Prep ey0 p b1OA}{1 neg}if/px eq{dp 0 ne 1.5 st -1dv 3 0 1 AA}{ a m2dp 0 n L/gs/gsave 1.2180 tr/dy 1 lp arc neg 2 x}if 0 ac mv mv bL rO px cvsc2 0 SA x 5 0 2 g neg1986,lp bd 1ne{bW 180 3 a ac L/l/lineto0 fill 0 l g/wb 0 4p 2 0 4 -1gr}b/In{px OA o pp}{sqrt at gr1 12ac gr p m chemdictpx o dp1 SAsc dp 1 rO p eq{gs mv 0pnp s wxexec 36 e bW psmexec gs o 900.6 pyput ldvpx 0Scientific 2ac6pxcXnparcbs 2 lWstp SAcpal39 pxixm/aL gr fillgpAcm 120 a}{ex3.375 n1200acbsst}{Ascx pypy 1-2DA}{cwsc}b/Ov{OrA grpp o -0.4Bd fill 26 gs-1dv0HA}{dL neg}if/py DLBxrosm0np24.6sl 12gs lpopysetgrayacSA 1mgrl1 1acgsdef/L{load sc np8ix pxdvlppymp p 81py L/ie/ifelse 2py5p2 gss0180SAfill r23ly e gs3 L/mv/moveto x elW sg -1 gr} cp1cmscmv mvlarcn145OB/bL n/eylt{-1 mcmgsLBalComputing, gr5 sc 1 OA}{1.5S setdash}d/cRg 3 py sc mvscst gr l5slgswx radbdDA}{cw py 16type[]type sOA}{10 cY cpsm dupwyrO cmsc 8 px 0 nH31 dpp2 180negnegatfillr grdict8pxp1-112ne{bW0mvgsrev{neg}ifsmnstpp}{2 e gia/pyr}ifg 41 lpn-2 a -8py -9.6-.6p5st mvpxbWxnegm21.6stpSA sc4rx2rO1wCBm wycm27pp}ifelse 4 1gr w L/m/mulpp rde st}b/OrA{pybdcpwyacdvend}b/Db{bs{dp sqrt0st}{0dv016mv10gpyglfill}b/SA{aF ppsm}b/CB{np -1cwl mmWI0ppxex0pySA100mtl}for0m}b/dA{[33 90r0.5cvgrfilldef/b{bindbs st2dv/bdpdp180lW rO x RA}{6a}b/PT{8nst}b/HA{lWrotpyaAdxDLB pxarclW eq{DB}{DS}ielpm2smgi ZLB lt{ppDT}]o gso/c SACopyRightscL/xl/translatedp-1cptdpssc -1-10sc0ac2.2rObeginInc.clippathAA}{1lW0OA}{1cm9.6p l dp/cYdvsmpmvnpmvixroatSAcmCAxla}ie}b/BW{wD16-1dvsbscppx1.6p27st}{px1SAx2wbst}{1.0xA ppdprlt{1pywFelp201n/ex8scm1rO bW0xlrot mbegin/version0lxne1o-1gsmtsor{41gsS0.4mcprad 1gr}b/ 0wChemDrawpLaserro-1cvpeq{DD}{DS}iel 5r-4.8CBsgbegin0a0ppw0est}{Ascfill25.8-1x}ifsca/pxaco xl 0fill-2s{dp1.2clip}b/Ct{bspL/S{sfxL/ix/indexs2.25ppwDxnp[{pysm2cmxwe4.8lalDA}{27024.6DA}d L/tr/transformOA}{1aRdp0-9.6m/waca}ie}b/WW{gslCAxcWprlinetoWIdivl0pyfillradsetgraypp wL/n/ng L/gr/grestore-9.6OBcounttomark{bs-8py360pgi0.6n/dyxl}{xlgrpcmmcmrocppst}]ecpt1xldvZLBix0xlap userdict/chemdictmvnpaLdpsce 0g-.6scgr}{gs-11rS]}b/dL{dAlwxoataccm0smputrendap0.5roundpxdx %2gr 2exec}{alaLl16.80.3DA}{dL01.52.20p0mvedywF2msgelpcmbWlcmne{bWlpyg/bbpxdvatpyg/cXcua o -1rOb2 m m n sc py mv 1 s dp p dv -1 x CA p fill rad 2 8 g neg dv/bd p lp p dv}{bd}ie 25.8 DA}{2.25 sm sm 0 e x/dx 6 DA}{dLOB px sg np n/dx -1 cw 1 L/mt/matrix 2700 dp g py S}if/lp1 dp 0 def}bind mv ro}ie}b sl tr bd m eq{dL}if px 1 ac 4 CA 3 -0.4 (answer) 2.251987,

Problem 2.5 Which structure in each set does not represent the same molecule as do the other two? a ) () C i H H H H C 3C 2C 2C( H 3)2

(i C 3C 2C 2 CC 3 i) H H H H H dict3240 DSt [6 I 8120 2080 DSt [7 I 8 10 12 13 8760 4020 DSt [9 I 8336 3440 DSt [11 I 7660 4200 DS 70 begin SP C H mdictmvs2.251SA-11r-1.6bWgsecp27dup4stac0.4pdvixst}{1.0x1gspymvdv0pxolsml0g0cXpx0py-1gi22m0pp}b/DT{gs m}b/dA{[3lWrlp-2xsginesmg/wbs0st4.8putpxg01def/L{load360ne{pyn1.5L/a/addatd/aRlW42-1d/aADA}{3st}{rs wSA165neg}if/pxdvOA}{1Inc.lp1llWst}{pxgr392sleq{dL}if26def}b/d/defm0bdlWpygrst}b/DS{npppppsmsc3nSq }ie}b/BW{wD6pxcXiinpppac2cm2pygrwyr00pxmsc180pp-2dxLBxgseppxl360rlinetopiYradp0lAA}]eexpxcp}{psm }ie}b/WW{gs2beginsmv27cYclippathst}]e4setgrayaBdSAL/n/negm1st}{0p0apcm-11gdpInx5pypppxL/ro/rotate 0v}{bd}iedpcw1oscwyrlinetomsmsmdef}bindgr}b/In{pxap12arcaRw xxsd/aFmpwFeaceqoand{pp gSA-1dxlWdv A}{1 pxxLB0gs16rODA}{2.2523eq{gsrOgs1al1-1mvpxm/aLpacs{nHg/cYDA}{120slL/pp/pop plmvl nspxnp}b360f em0a04x12al w CBx}if0filldef/b{bindmpyg/bbnppyxlppw AA}{1gi1alL/np/newpathL/al/aloadcWCApcmst}{gsac y0g3600-13neg 1 cvlp0aarc0mvne{bWpl01dv/bd r}ifround0 scl4w pn0-1 Ac}{1.00Ov}{0.5px4.8 glx cmexec1DT}{ gr}{gs010.5Computing,posmmt270trst2grpcpt x}if exec9.6x21.65pcYraddpcv4sgm0lpx lsetmiterlimitags 0llpdpp pscpg sqrtrO90 0.5 0dpl01dpggsst}{AsclradlWx scg0sc-0.4r o/cXexec}b/CS{pwpeqs12pyst}{Ascdygi0aland{bbd pyn/dx-4.8rpysg filldv )ly 1bs1.6cm1.5mv1DA}{270sg0fill currentmatrixeppgr9.6p xdx n0.25dv gsrO4cp}b/ZLB s{dp ac edy2pp sgnp[{pyw0 scmv pplAA}{1m pxat4ro}ie}b/AA{npgr pp bbpxo0 fill m o0.3aclcm dvwxpy s/b1 spylp smscacac2 py fill1cppxWIdivOA}{1.53 ac OA}{1cm grgopxsmmvdp 0gsmv py 180lWpy 4.8 arca d/nHpsl} S}ie -1arcdv/bd scW 23 osc}b/Ov{OrA0S -1-138radCA nH3pxsg s/wxs nrOAA}{1 lp0cw2p6p p al4 mmvly sgsfill y0p-1 begin/versionL/mt/matrix x bsgidprOlt{ppDT}]o pgr}ie}b/Cr{0DSd/WI{wxdv/m1m 1 p1.5LBdppr gr}b e24.6gs 2st}{0 megrbs ecmpgr}b/OB{/bSap cp2 1 a/px go-1e-1s18 1 smnpoa2180dp 3Ov}{Ascsmlpsl spsgb rot sc type[]typep 0lp aclgr16ppp}{2 e ZLBwcve lW0g/cX OA}{1 2 dv r0pcvi/nSqosm ne{wyldp cv s sm RA}{ .2180 rpspyCBrev{neg}ifrO00 sm1 4 2 25.8dv wb24.6 n x wbr fill 0rO 2.25 dx OA}{1 eq{2 st}b/Ar1{gs-1 x3 m slgi180eq{DB}{DS}ieSA fill}b/SA{aFo 0.5 3 lWrO Ac}{0.5 120 px SA CAgr 8 ap scdv eq12 ey end ne{bW mvS]}b/dL{dA 0-1acm rosm1 alendx sm}b/CB{np[{[{CS}{CS}{cB}{CW}{pp}{cB}{CW}{pp}{ t}{Asc 0L/l/lineto16 cm at ne L/mv/movetox wx4 1 gr}b/wD9.6 16.8 srad10mveq st}b/Asc{OrA sqrtst}b /ix/index 25.8 0 begin cm gslor{4fill 4 cm dppy lp xl 1aLlt{e}if0cm gr}{dp 4.0 90 pL/r/roll45 pycm6m p5 -1 gs 0.6 n/dyxl}{xlgr lpp}ifelse SA a/py o ZLB DA}{180sc dict lpnpst roDA}{90 r cY p l}for stsdv 1 2 r o wF e x lx p 5st pxwcp bd ppsetdash}d/cR dv cX 3 dy s/wy x o DLB arc 1 2.2 DA}{cw n 0 0 e 6 neg x/dx cm Scientificp l m eq{dp py p l bL 1 SSA sc S}if/lp cm dp/cY 0 ac mv sc rO cp a gs 1 27 gr l DA}{dL CA ( 0 px OB wD np wx px cm SA setgray p 0 p cp gs L/m/mulgs l d/wF sc np iX arc gs bb L/at/atan L/cp/clo gi pp-0.4 ix ac lp 2 cm fill p bs p lp sc 2 dv 1 -1 0 CA sg mv bL nSq e cp mv 8 m1 LB pp cml} OA}{1 10 5 m s 2 C3 C2 H H C3 C C2 H H H C3 H (answer) b ) (i) currentpoint 192837465

(ii)

(iii) currentpoint 192837465 (answer)

Problem 2.6

Show the structures for all of the alkanes of each of the following formulas. a) C5H12 (answer) b) C6H14 (answer) c) C7H16 (answer)

Problem 2.7 Based on your answers to Problem 2.6, deduce the number of different alkyl groups of formula: a) C5H11(answer) b) C6H13(answer)

Problem 2.8 How many different alcohols are there for each of the following formulas? Show the structure for each and provide each with a common name using the system described in the immediately previous section of the text. a) C3H8O (answer) b) C4H10O (answer)

Problem 2.9

gr end /bs[]d Db 147 13 34 71 48 45 19 20 chemdict begin SP

x p -1g np e 2.251987,m -1rosm 2.2 16 In DA}{cwLB1 ppmv px 1.2180 0np180 o dv/bd 0 -1.6 16p 0 1.5 1 wy m2dp 0 n egs -1st}{0 xl p p chemdict neg}if/px 1 fill 1 0 ne 0 p st -1np s 0 1 SA p a -1 gr}{pp}{gs l Prep ey0 e ldvOA}{1 arc al cwSAeq{dp mv mv 4p 2 r 4 -1cvscix0 fill x l 5 0 pxrOCA L/gs/gsave -9.6DA}{cw g g sm0.5p 1-2scl23 0 l g/wb 1sm ldp 1 dv owxexec OA o pp}{sqrt at 5 o ro dv 1ne{bW stp 24.6r-4.8 2ac6pxOA}{1 1 gsp eq{gs st}]e gsdef/L{load 360 e bW psmnega}{ex900.6 n12021.6px 3 a sl pypy 0.5cv 16 acrO 2 lWsm SA00psetdash}d/cRg d fillgpAcm exec L/xl/translatep n/eyp1800Scientific90 16 x}if sbs 0 5n3 sm mAA}{1 w gr}b/In{pxo/cX gs-1dvmv sm gr lgr1 3.375 pyput ac0m}b/dA{[30.6n/dyscWcm grw ene{bW e dv/bd1sm}b/CB{np np8ix scmv wF1986,12py at0Cambridgem02 gs 0180rev{neg}ifsm sc 1 ropy 4 g/bb x -0.4m/aL sc p cp1cm0mnegnegat counttomark{bsst}{AscxscnegSA m rp0lycpsmcpL/mv/moveto o eeq{dL}if263c py sc 180WIpym0 p145OB/bLcm1-12-8SA lp type[]typerOgrfilldef/b{bindbs st alDA}{270sg -1 -2 aL dpp2 mvscst5st neg}if/py DLBxmvtr/dysc p gsLB0ac2.2xpbeginInc.clippathgrrO25.8 L/m/mul0 nH3g -8py -9.6-.6ppmvpslgs gr end}b/Db{bs{dp 4r0mvComputing,ppcYstpp}{2putcpalac dpxl41 lp0gr}i st}b/OrA{pybdmvpxbWradbdm/waca}ie}b/BW{wDCBsgedpcm27gsSA OA}{1.5S cmsc8 Bdpp rdef} -1cwl mHA}{dLcp16.80.3 negmpCAbspy5p-1pxarc gs rllpfill np[{py0gpyglfill}b/SA{aF pppx2pxlW 9.6a2 RA}{6a}b/PT{8nst}b/HA{lWrotbW12gr}{gsx12lW eq{DB}{DS}ielpm2smlpygia/pypcprad 1gr}b/w SACopyRight-9.6OB81SA1 L/ie/ifelse0a}ie}b/WW{gs2wDcXnparc-1pp}ifelse gi ZLBcptr}ifgpy cmrO o4 l dp/cYdv120ppxex0pyixfillpgr pxrad-.6scne{bW-11rCBsgbeginprlinetoWIcmwe4.8l1end-1xldvZLBixnxlx1w ppdprlt{1pymvlarcnfillr-1cv0m1rO0glt{-1py scmv2.25ppm-10setgrayacmtsor{4fillradsetgraypp wgsgrAc 0wChemDrawpLaserlpwxdictmtl}forxlxlrot360pgi3S]}b/dL{dAlwxbs02cmxstbL1gsS0.4xOA}{1g/cXcurr xl 0fill-2s{dp1.2clip}b/Ct{bsscmpyaAdxDLB-10sL/l/linetoDA}{cwsc}b/Ov{OrA2grppap0.5st}{1.0dxs L/tr/transformOA}{1aRdpDA}{dL01.5cp1cmbegin/version0lxne1ooatacdivl0cppmvgrSAmx}ifsca/pxacxL L/gr/grestoresclp201n/ex8sceq{DD}{DS}iel0sqrtrOOBCAxl}{xlgrpcmmcm0dupwyrOlW02wbroundpxapuserdict/chemdictmvnpaLdpdp-1cptdpspym5ac20st}{0opywymvepx1.6p27st}{pxpxpxdvat24.6DA}{ %2gr 2exec}{alaLlwyacacx0SAL/S{sfxL/ix/indexsedy25.8dvdv0a0bWlcmst}{Ascfill1aclt{ppDT}]oL/n/ne o s dvlp0 m msgbd py 2 b1 8 0 neg dpw e x lp p 1 dv b2 p 2 x -1 dp np n sc 8 0 p ro dv}{bd}ie wF 2 DA}{2.25 sm 0 0 e x/dx 6 DA}{dL 1 px L/mt/matrix gr}b/OB{/bS 3 180 0 1 n/dx -1 px 1 1 sg np gs dp sl def}bind py S}if/lp 12 270 tr bd g mv a AA}{1 px m lW ro}ie}b/A 1 39 4 CA 3 -0.4

gr end 2 ]d [03320 141 2740 3440] [1 1 2960 2740 2960 3880] I 2960 3880 DSt [3 /bs[[141 3320 3440 2960 3440] 209 60 I53 344048 45 19 20 chemdict begin SP I 3320 3040 DSt Db 3880 DSt [1 3320 3040] 3440 gr end /bs[]d Db 265 13 34 71 48 45 19 20 chemdict begin SP x p 0 dp In DA}{cw wy m2exec}{al ex lsgdv 1m mv L/ix/index L/l/lineto lp 0 lInc. st}{Asc 1 lW1 x py 1 DA}{18 a bW 2dv sm e 2 p 8bW gr 2 p sc cm gssc OB pxs1 dvl cm mv m dup py end ppL/m/mul 1o 5 g0 cm negOA}{1np 1.2 p0 chemdict rarc 0 0.5cW bs e sm gr}b/OB{/bS -1 e lWBd rO dvsg o -1ix s s{dppmv 1 ac0.3 m1mpac 12e DLB sl e0.5 1 eq{dp o -1 smor{4 ac np 0.5 ppcm 360 e 1pp}{sqrt a}{exro-1 at py DA}{cw 5 -1 neg}if/px sc p fill gr51.6cm1.5 stg/bb0-1scatZLBgr}b/wD fill -1 psm-11.2 n 16.8bdpdp cmCAl xl 1p a -1 1st}{01 m L/mt/matrix27st}{pxgr setdash}d/cR x cm gs pApxrO 0p1 neg}if/py DLBx-1g-1px s30m gsgi3 lW sg x}if np dpat sm fill}b/SA{aF2 dproundacpacwa np fill 180 0 nneg at lprPrepxne{bW 0cp06 -1 begin/versiondplybWcm 310rom 1 al00wcvslDT}]o 0gspxlex cp 8p sc dvCA-9.6pp 12acend}b/Db{bs{dp0sm2.25 lSAfill lx0 rlineto div lw4p e ZLBsetgrayst}{1.0olpgi py sc mv exec l0st}b/HA{lWrO py aAdv}{bd}iedp2.2 -2 wy 1 prOWIcp 00bL 2rad ggs wb01CA 9.6def}b dpCopyRight p aLwy 1ix x py 0L/S{sfa}ie}b/BW{wD6 py rnpac0 lacclippath st}]eSAgr}b/In{px apgslt -80gr m g 12LBl lL/xl/translate-121.6st2.2gsc sqrtrO ppbeginsnesmcY mt OA}{1.5pcpt pywx m/aLOA}{ st}b/OrA{pybdLaseraR8 scSArotbWxOA}{1px0mv2116xx 0cmwx w0acpx1pygr0l25.8dv eq{dL}if-234wb-1py -2HA}{dLmv pySAdictpx180 180m lp 5r012al wrev{neg}ifpsc}b/Ov{OrAdv/bdopx radro}ie}b/AA RA}{6dp WIpyegso counttomark{bsdx24.6type[]type -1sg0aarccmmeq{gs 4stgrlt{pposc execxl x1Ac} SAChemDraw1986,145fill 0l8scm1b1dpgr}{gsxLBCBeq{DB}{DS}iene{bW dp11alpxOA}{1ixnHdxl-1p l cwrlt{1scst5stclip}b/Ct{bsdpe0dvbsm}b/dA{[3pycw dvOA}{1o0gspp}{2 mvSDA}{270a0lWAA}{10 ppdp-9.6-.6 pscm2.251987,L/ie/ifelse0np01804arcrnegCBp0begin27gsscs 2sm pbdcp-1acr}ifscg/cXcurrer 0wp2l2-1mv mvarcnn/ex radppn/ey 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In DA}{cw a}{exst}{0 ne{bW a}ie}b/BW{wD1 sx fill ac cY 0 p def}bind sc sg0 0 gsp wy m2 dp LBe p p ro cv 0bd2 b1 a}ie}b/WW{gse pcW rlineto g py st}]e g OA}{1 SA OA a bW 2 mv n at n 1 3.375 lL/ie/ifelsest}{Asc 2.25 rev{neg}if at p sm pydv/bd 8g a lWAA}{1 5 g-1 sdp -1pp mv l145 m1 L/S{sf8 24.6 begin/version 1 sc}b/Ov{OrAac setgray4ix n grl 12 o -1dvdv negpxp16.8 dp dp n/ey 2.25 neg 0 0 S]}b/dL{dA opy eq{gsl ZLB al ldv 3 CAnH o -1 e 20 ps{dp1.2 L/xl/translatel}for sc06 m neg}if/px-2 psetgray SAfill}b/SA{aF cp pxBdrO x lg fill pp}{sqrtneg wy8 px -9.6 x l p stpyDLB -4.8 CB12 sg dv ly1def/b{bind gi25.8px sc lW4g/cX dvn gs gr scHA}{dLexmv SA 08 m 0-.6 -8 ne{bW 0.6 2.2 -1 DA}{2.25 nelstem stcp lt{ppixL/m/mulx de np fillpxdvCAbdlneg}if/pyDLB mac 0cpmp-1 -1LBpy l CBDA}{cwInc.gr}b/OB{/bScm m py-0.4 r 21.6 cp 8ixmvscst sc clip}b/Ct{bs put g xxlL/ix/indexalac0.5eq{dp rO5 p3 wL/mv/moveto DT}]oac 3cm py scrmdv sm-9.6 l00ac0.3 DA}{dL lpxrotsc 4 gi rOB1 cv np[{pyw0 est}{Ascfill a/py xdp01a/px p gLB dppp -2g-.6 ppe aLofillnbddictp epcpt20m}b/dA{[390eq{DB}{DS}iepxlW gr24alr 0.4 py 24.6cm0360 -81pA180execL/gs/gsavepyscDA}{cwpy-1 rr -118016rO 0np0smmvsm 1 4.8 e1 grw -1r}ifscw-1DA}{1 st}b/OrA{pyIUPACcounttomark{bsnpcmDA}{dL sgdv cX0larcdp mcmdupdpSlW setdash}d/cR-1e -10cmmvpymvmpp lp ix pnegrotCAbsdv}{bd}ielWpppx l16 npgrg 2div2cp AA}{1mxmvround-2dxw RA}{6sm0wF1Laserr 0.601.2-1rodv12gr}{gs0e0.5n/dy01dpnepesmcmro1.5mvg/bbppxat180ppxaclpc SACopyRightmvst}b/HA{lWcmbWdppyScientific2rlpbegin23pp-1 0cp270lp10end 13sm}b/CB{np[{ l py -9.6xneggrgsat 90-1 end}b/Db{bs{dp type[]typepywyagrl0ac clippathstlgspcpto0.5xlpp1pgr}ie} ppdp lt{11205OA}{1wx 1nSArO10 1.5e0plp gss2 neg6SA0rlx fill27l16scpp}{2SAgi-1xgr}b/In{px2o/cX 0wChemDraw1986,sgacatey0180 xOA}{1 5arcdpComputing,0cmne{bWrOputpp-1eeq{dL}ifapL/n xl cwl2exec}{al02.25 gr x0eq{DD}{DS}iepxspydv/bdfillOA}{1pxac127OA}{1.5002s-0.4S}if/lp3Ac} L/tr/transformlp5OB12dvscxpym/w 180sc16smmvpcwwDsgsL/mt/matrixor{4radS391dv2execxlsc14sg L/gr/grestorestcpslgspy radCambridgex/dxac12acw2pxxl}{xlcpcmlpsm0st}{pxpxappprad0lp9.6curre userdict/chemdictn/ex aL1mtp0pyaAps13600x1dywFSAox}ifmv1obs2pm0xpbLfillgrDA}{270ro}ie}b/Ag %dp/cYmWIpylarcnpyPrepgrdpmv 00dx30a0sqrtst}{0mme-1.6bWgsmtmvsm0bd144dvx}ifst}{1.06pxop p cm b2 o Provide 1 0 lp gr}{pp}{gs np a}b/PT{8grm aRfill m rad np np 1987, p 21.6 2 mv1 ro 120 sm SAg gssc25.8 sc begin 1.6 s 4 wy10 ac wb ZLB gr}b/w 1 bW -1 sc px -1 chemdict p 0 1 CA cmbs st l bs 2 rO gs o px 8 OB/bL -1 ac tr/dy n/dxsl o gs e x gr wx g/wb 0 lt{-1 180 x 3 L/l/lineto0 cm pp}ifelse g lmv rO 2 arc px lp p p 0 gs sl tr n WI 1 np def/L{loadx s{ SA sc 1 gs w cv wx m/aL a fill v.3750xne{bWaAm}b/dA{[3dv/bdpxOA}{10-1pypp}{2pSA0SScptdef/L{load26x21.6fillcmdypxgr}{dplpsc890eqa b/HA{lW-121.6stL/ix/indexost}{0 -2cXlxmve0mvcp2704.8125.8setdash}d/cRx1wblt{e}if DA}{120arcxiYg0bbm pwxaLdpdpmv-12-8pyn/dx xs0rCB16ox}if0npdp50mst}{Ascbdaclt{ppDT}]oAA}{1wx0alCAs 0xrOgs4m0wF0180lWpl1 b/Ct{bspxradlt{-1SA360-4.8dp1eq{DB}{DS}ieSA27dup12cppcm2e8ixpp 1fillL/n/negnL/np/newpathL/al/aload4.p n-1 dictCambridgescppxparcneglp -1DA}{2.25elpmvlbsAA}{1391smvpy lWp-234lpd/wFpp x360l0wxobs12bL0.25c sgacradbdm0b1002.2cmmv120OB6 dvbeginsmatclippathst}]ea/pysclWZLB nH312exec}b/CS{pgrsgpy sm eqOv} aRroat l120pbWxa}ie}b/WW{gsrev{neg}ifgrcmcmL/mv/movetoOA}{1w DA}{180mv0sgrs/wylW180em st}{A saveDA}{dL0tr/dym0lppxs23acpppxcWpbsdef/b{binde0lstalrOsetgray1-0.4ro/cXgirs/wxrO2.25pSAmv4.0 dp42 ounttomark{bspypymbegin/versionr-1.6bWg/wbls1 py efill DA}{270pxa/pxgdxs{nH2mvdpnpac10mvpgr lne{w 1SA100pput1gaca}ie}b/BW{wDl2 rOedprlinetoacmxsmgrdp 0algsr}if0exec9.6ol-1ne{pyn xlfillsmpOv}{0.50.3L 45OB/bLrotCA0OA}{10sqrt0.5w CBpy023cmoacWIeq{gs put grwcvwbwxg/cX scAc}{0.5120 d/aFmvofilldv/m1AA opysc1pyl}for 1800180-1-10.6Computing,ppcY2ne{bW rO1 1lWppdp1801 0ac ac -1 dp/cYppe0cv0ldxCAst}b/DS /ex xn 8scprosmscne{bWgi rOpac2 filldvnecpcmsc1p wpdef}bindxp3dvst}{1.0 dv e1smgr smnprlineto0dp onSq yixfillDLBL/S{sf xlgr}{gs 0pylWr CADA}{cwsc}b/Ov{OrAgs4SAomxatsc ix gr}b/wD sc11.50AA}{1 sls l dx setm 0gr end}b/Db{bs{dp 5neg}if/px cvsgsa111 px pdivrocppygrpxdvgr}b/In{px360 arc-1cY 0 dppx 9.6mveq lWan 1987,ey rO py bscp3 1640x dy cwe sgnp[{pyw1.6cm 4p 4wypp-1 dvxl44 0 n OA}{1 9.6scDSd/WI{wx px pypap rPrepnegm0lac dps24.6gsLB pysg x1lL/mt/matrixlW st}{pxend-1osc24.6 gs gcm2 se rad 0cvi/nSqo ro 3lp p 80.6 m1 cmcpt12rot -1 type[]typem16 fill 2716pg0fill}b/SA{aF0x}if sg-1 rO px px aR dvL/a/add0 OA}{18o 5 np p-9.6180-.6 8 0 sc sl scal2n/dysc p 0llyo smcm2smgifill1 0 g scground xlapaL r5 18 st}{0pnpst 0 cw 2rO -1 2bd 0py0n/ey1.5dv}{bd}ie 90SA seq{dp p gs2 sm1.5 2str 4 m sm}b/CB{np[{[{CS}{CS}{cB}{CW}{pp} if/py 1.2 DA}{cw 5 a rarc180 0.5 x gr arc 0stsm0 smmv 0.4 0.5 S}if/lpdef}b/d/def cm bdpx2 -1 gs st}b t}{0 L/ie/ifelse npg 2 ac2.25 2.2 0 0wy0 lInc. 3gr}b/OB{/bSpx px a cm currentmatrix s rad g p 1mvpInx bW eq{DD}{DS}ie sm L/l/lineto fill acbslpp}ifelse l0rad-1ac L/m/mul gr}ie}b/Cr{0 m p s oap cX DA}{90 c0.3 SA m/w px DLB gs1 25.8 xl}{xl0 rO gs pxst tr lZLB 1 py 0 lp gr LBpcX 3w n bb ap L/pp/pop p anslate x dv l dx1 -1 r e wF wD np p p g ne OA}{1.5 ap cp 3 pp p gspyp dv dv grp e chemdict dp m 2 0 st}{Asc mvgs 1 p setgray mt or{4 g/bb np eq{dL}if sc mt -1 p p 6 DA}{dL SA lp gr n sl 0m gi px cv 8 e x/dx ScientificS]}b/dL{dAwx pg neg l 1 begincm m 1 bL dv/bd -0.41 SA l rad 0 2 CA ro}ie}b/AA{np Ac}{1.0 eq at ac n-1 s Bd m/aL o gsg/cY o iX cm p px g -1 m dict pp l sg 0 1 16.8 lp m py 6 d/aR gr rad 0 py a3 2 3 ) ) C currentpoint 192837465 ( 3 H C H ( C C H ) C H 2

St Db 7500] 45 19 20 chemdict begin SP 6660 (answer)

b/Ct{bsdpmvlt{-1ne{bW-1odyComputing,dpcYlpeq{gspbdSpxpxppylW0m/aLpxlped/wFcYDA}{120p-1legsst}{As swxaLxne{bWtr/dy1180begin/versiondparcrOatSAs2wepstZLB4gsdvgroundp2aplcmxndp/cY0fillnpwdxL/al/aloadxld nf/pyDA}{dL01.5pspylpmv12dv/bdpxDA}{2.25acsmsmdef}bind1x}if180wnHcurrentmatrixs/wySAarc0st}b/DS{ aRfill0eq{DD}{DS}iepxpgi180n/dyeq{dp10ocmsm0L/mv/moveto-0.41-0.4nscpx ne{py1dydpsma0opyL/pp/popL ranslate-1-1ac0pxpy n/dxarcdpw62-10dvnpsmgnWI27ropAA}{1gacdef/L{loadgdef}b/d/defsmcvi/nSqmrog3pxpy2 8-1 radpyxppy1800gpDA}{dLp1rev{neg}ifesc}b/Ov{OrAgirend2r}ifwx1SA-2oAc}{0.5dvx3600iX0eqcXmmv 401p ounttomark{bs2.2p16sqrt0acacpxxl}{xlpdef/b{bindmst}]e039 OA}{1lWDA}{180scgrscmnpnpstslmv ldp4.854 oSAdictmtradac08rotscpxx20.5 cw cv10p0lrlinetop3 sl1pytr1wyppnpgr}b/In{pxL/n/neg2L/np/newpathd/aRpy ppl e yix 1nSAputlcpt12L/ix/indexst}{0 rOxpL/mt/matrixxdup42dv/bd-10.5py g/cXgr4wbgs-10wpp0d/WI{wxpx radmgi r/HA{lWrOro-.6OA}{10-10erOS]}b/dL{dAwxsmcm OA}{1.5Ssetgray3BdAA}{1gir2 1816.8sbbom180 dv/m1In p savenegrotbWbsst}{Asc s13al 2.2 oDA}{cwcmeppxfill}b/SA{aF mL/m/mul6xgow0al03 st}{0opxl sgbsx sc0lp pcW 0gr scgrsce0 dvstcpsc -15gsscneglp fillsg0ne27gs 2cppstcppy1rOmo scixpx ix 0gr}ie}b/Cr{0dp0spmvwF4.0 8nSqac 20.60py0m 0b10scSA m type[]type-2OA}{1lpwgsdiv 040gi fill 1lW1 3dv exec 0 OA}{1s/wx 0rnepp apmvo p ono 2sc /ex end}b/Db{bs{dp 4 x0.6 pp sgnp[{pypx mg0 or{4l25.8 cmscp0sc 0pp 360exec}b/CS{pl lW2at0 cwlW apm 1bdp0eycm g aAm}b/dA{[30 sg xcW2301Inc.scmv1.5rOg/bb-1 esc st}{1.0112pxmv n DSd/aF xg0lp dx 90 AA 1987,L/ie/ifelsepy0ScientificlWlSAdvbeginp -1stne{bWl mv1p wx px24.6cmr o/cX-1fillcm 0pxbd 9.6mv 1800.25 np xDLBm1chemdict gsLBL/l/linetogrmvgr16 mt lst}{pxgr dv scxlS}if/lp xdv arcm 1200pprlinetosm setmi 45 atlm l}for xxle24.6 ac py25.8begin fillppmv pp}{2 2stcp-1setdash}d/cR21.6 1 aRrOxl AA}{1 ps 1 eq an t}{0-9.6 DA}{cwm3600 2.25r 1 p cX bs oac clippath elal 0lt{ppl 2 1CA9.6 3 LBlt{e}if mcv px OA}{1lW py bW m1 180 dpgr}{gsarcr CBeq{DB}{DS}ie ne bs dpacSA wb ZLB gr}b/wDs e radL/a/add CA dp st}b/A .375 dpp m/w l-8 DLB smmv 16 py-1.6ly bspp}ifelse 01 40.4 8xrad lp rO x -1 py CAAc}{1.0 o 12 ac 0.3-1 cac 1.2 n/ey 2 npcm r 0 py CBml filla0 050 st}{Asc gsDA}{270pp1 xl dxgs 9.6 sc 2.25 pcm bL ne{w g0.3 1120 CA a}ie}b/WW{gs 0.5 enp1bW 0 gr}b/OB{/bSap oDT}]o gs 1 s{nH g/cY x gr}{dp gr 2Ov}{ Prep 0p p sma}ie}b/BW{wD CA r wyac g/wbllW4.8SA alcv dp 4 0 ac ac p 5 ppdict gs4Ov}{0.5 rO py 8px21.6 dx x/dx dv Cambridge302 neg}if/px 0 16 cm 1.61270 grput cpt eq{dL}if dp bdL/S{sf dv}{bd}ie OB 2 s cm cp 0 m p fill a/pymv sg a/px aL sm sg rO lp 10fill iY bb px cv ro OB/bL 2 p sc 8 -1 6 a -4.8 wF SA lp gr l cm sm rad x sm}b/CB{np[{[{CS}{CS}{cB}{CW}{pp} 5 g sl neg l 1 wD setgray 90 e x}if gs 1 sc lx 2 m e s py bL gr pp at a -1 0 0 ro}ie}b/AA{np 1.5 rad gr g p 4 fill lsg cX1 p mv dv ac gr 8 eq{2 DA}{90 py -1 eq 6 bH ) 2) C ) 3C C H C3 H ( C 3H C H H C 3 ( C H currentpoint 192837465 H C 2 H C H 2 2

(answer) gr end /bs[]d Db 223 13 34 71 48 45 19 20 chemdict begin SP c ) x 2 -1 rO In DA}{cw wy m2 dp LBl p p 3.375 SA x g a}ie}b/BW{wDCAcW 0 at pp}{2 ZLB ac eq{dL}ifgrl 12 s a bW sdp sm a}{ex12 cv m1l}for xa}ie}b/WW{gs0.5x fill 1 1 sc}b/Ov{OrAgr g dv sg0 gs o -1 d 5 g-1 ps{dp bd n 1 lsg ro 1m n/ey stdx30neg 2.25 rev{neg}if0bs p py pydv/bd lOA}{1 ac OA}{ o -1dvdv -1pat0 wy8 px 1.2 rot b1 2.26 -1 0 0 CBl 1 sg psetgray ne2 L/mv/moveto 3 ix-1 p Ac}{0 e 20 mvpyp5OA}{11dv 0L/ie/ifelse SAm gs0.690SAsDA}{cwac e127dup 25.8cm 8ixL/m/mulpxo f fill pp}{sqrtppxp16.80.3 py mHcpm a0 begin/version larco cY px 0st}{pxpxsetgrayro}ie}b/AA{ gs gr scmv nsc L/xl/translate2lCA0xl 24.6 neg}if/pxpeq{dp grpyne{bW gil0 a/py sc pxBd AA}{1ar np pApxdvlp1.2 lmv acbddict cmcptdp 05 sc -4.8 25.8 -1 rnprlinetomeq{gsst2ac al cp py4g/cX 3 w 2x cp 8ix180 nege clip}b/Ct{bs-1-1 -.6 scne{bWLBpy12 fill dv lysm 5 2m wsm stcp px mvround r 21.6r9 py scrmvscst-9.6 l0fillnacscxpy mac bsdv}{bd}ie0 2.2 -2 np[{pyw1.6smste mvg/bbpx-0.44CAn-2 x def} dppp -2 HA}{dLexpxaRfillDLB epbWpxL/ix/indexalweq{DB}{DS}iest}{Ascrad 0.4 py lW-0.4gr}ie}b5 -81fillmg-.6mvm2.25 SApDA}{dL 12m}b/dA{[3p sg cv 16 npldef/b{bind AA}{1mxm 24.6cmscxcmga st}b/OrA{py mvpp counttomark{bsnpcm 4xpydv/bdpywyagrrOg 0cprop gr e11 w setdash}d/cRLBcX -10cm2dvexecL/gs/gsave-9.6 DA}{cwsc -1 -112r1acedv 0lp23pp-1 clippathl fillS40x2sdp0ZLBpDA}{18 RA}{6sm0wFstcpsl 90ix end}b/Db{bs{dp type[]typeox}ifmv1dp2scg270mdpend -1r}ifaa/px0 g-1er0m SACopyRightplaLo0lp -1 atgrdpmv l20gr}{gsarclWpppx cX0nepcmlp30xcpp1gspcptoewbsclWxlapL/n/n l py-9.6x120negst}b/HA{lWrO10 180pylp rx-1 neg6SAebegin0gsmtmv4.8SAgi-10gr}b/In{px2o/cXex ppdp lt{1WIpyeLaserrPrepeyp1803-8pyScientific2r2pxxl}{xlbWcmgr}b/OB{/bSap pxat180pp 360py1 0wChemDraw1986,145 1negputdvxOA}{1 gsgi dpComputing,oInc.pcm1.5st}]elW 1x}ifexecnH314sglt{ xl cwl2exec}{alneg}if/pynl8scm/w 1.5rot16sqrtst}{0mx lOA}{1pxacdivfill}b/SA{aFpprad0lp9.6curren L/tr/transformarcnpygr x0eq{DD}{DS}iepxsmvwFlpbeginfill27smcm lsmlrOputpp-10.5xlpp1rOxaclpp-1 L/gr/grestore1gsatgspy radCambridgex/dxacs2 accwwDsgsL/mt/matrixor{4bdgrlt{ppgDT}]oSAdxlggin userdict/chemdictn/ex aLC20p 008e01805010.5n/dy00DA}{2.25sm lWbL24alrS391dv2st}{1.06dvne{ %dp/cYmneggrp5OBro0.60dp0p0pyaApsDLBsme18016rO1-1.6cpel16pSA1OA}{1.54cv3sm}b/CB{np[{[{ p cm b2 np st}{0 0bdL/S{sfpy1360sl sc OB CB dp ac mv 0 p def}bind sc 1 w gr}b/wD 1 gr}{pp}{gs 1987,ne{bW o 0 CA grmv dp H sm st}{Asc 0 gs 1 m lx cm 0 s 4 fill10 gs def/L{loadx s{n a}b/PT{82 mvnp np -1 wx mt 21.6 1 bW p rad m sc 120 chemdict r o L/l/lineto0 bs st l 0 0 rO SA o S}if/lp gspx 8 OB/bL C px ro -1 lt{-1 n/dxp 3 S]}b/dL{dA pp}ifelsewy DA}{270 m/aL wb ac tr/dy p g arc g px dy e sc gr wx g/wb bs p lDA}{dL 2 mv rO cm0 p p WI sl tr n gs 1 np sc 1 0 dv wx fill aL C( 24H CCC HH C C) C H 2 3 H 2 H H 3 C 32 H ) ( C H (answer) d) ) 3 ( 2 C H C2) C HC 2currentpoint 192837465 CH C H 32H ( C H C 3 H H (answer) currentpoint 192837465

Problem 2.10 Provide systematic names for each of the following alkyl groups: a 3) ) C3 HC C 2 H( C currentpoint 192837465 H )H C H ( C H 3 (answer) bC 3 3 ) 3C CC H H ) H ( H C ( ) C H 2 2 currentpoint 192837465 (answer)

Problem 2.11 Provide IUPAC names for each of the following:

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a 2 )3 2 3 CC HC C ) H 2 Ccurrentpoint 192837465 l H ( H (answer) b ) 2 currentpoint 192837465 ) CC (2 C C H H 2 H N C H C H : 3 2 (answer) . . c 2 2 ) N currentpoint 192837465 H C H C H N H 2 2 (answer)

Problem 2.12 Classify all carbon atoms of neopentane as primary, secondary, tertiary or quaternary. How many primary, secondary and tertiary hydrogen atoms are there per molecule of neopentane. (answer)

Problem 2.13 Draw structures for all tertiary alcohols of formula C6H14O. (answer)

Problem 2.14 Draw a sawhorse projection for each of the following molecules, showing all of the atoms present and emphasizing the bonds indicated. a. propane (C1-C2)

(answer) b. butane (C2-C3)

(answer) c. 2-methylpentane (C2-C3) (answer)

Problem 2.15 Draw Newman projections representing each of the following: a) a propane molecule viewed along a carbon-carbon bond

(answer) b) a butane molecule viewed along the central carbon-carbon bond

(answer) c) a 2-methylpentane molecule viewed along the bond between the second and third carbon atoms in the chain (answer)

Problem 2.16 Using a set of molecular models, construct and draw Newman projections of all eclipsed and staggered conformations of the 2-methylbutane molecule as viewed along the bond between the second and third carbon atoms in the chain. (answer)

megsst}b/HA{lW-121.6x-8pyn/dxarcdy12.2-1cXsbswxpxmpp}{2AA}{1cptscl2180a/pxcurrentmatrixs/wylsgarc4 wcmat090ixfillngr0cmlcpt2xlne{bW-1oraccwe-2OA}{1pcm2divL/mv/movetomscpyg/cX6x4lpwrr-1cm16.8bdgragppys mdictpxaRcvatl8dpero0tr/dy0ScientificCBl16opylpcmcp016clippathl4025.8cmr}ifwxm/aLdef}b/d/defsdpfillsm9.6cXd B1986,lpbW10SAmpCA180m0204-4.8 neglp rObeginppcmcm 0lpytrdp1rOsetdash}d/cRo/cXne{pydvxldpcv4dxbsl0 bdclip}b/Ct{bspxmvsmsc pysc5r0gi0dv/bdpxxr-1.6dp-1pynexor{4mvr0lWcvwbrad-0.4gr}ie}b/Cr{0x360pmvopy s pOA}{11pydictpputbWaA8sscmpx01180sg dvsg0lrlineto3mt2ro4.82g/bb-12scg24.6AA}{1gi01sm0st}{0pxlW180 p negOBroPrepnegl}for012gr}{gs x20.6wSAfillnp[{pyocY lpm 1bsgi1alacggsx}if px1-1gr}b/wDfilldvwL/a/addxOA}e dLp2l0fillrSAradmrotpy bsnpg 360parc0 Computing, 1sc}b/Ov{OrAstSgrsetgray0BdnHscpxd/wFmvDSsppSAOv}{ FalaL16.8graLxne{bW stm}b/dA{[3dpacpx0016nedef/b{bindbL plfillDA}{27043SA9.6pAc}{0.51.50d/aFpxcmx D yL/gs/gsave 0eyrO0ac dpe 5180type[]type x}iflxalye 5l0ene{bWgr wySAdvgr}b/In{pxgrwbe5paRradpxgsnpstslm atL/xl/translate L/S{sfOA}{1 begin/version wyarc wpp}ifelseput0ppac ssm}b/CB{np[{[{CS}{CS}{cB}{CW a}{ex1458sc0120 1gacpy 24.6-1 spy S]}b/dL{dAcm gspppxfill}b/SA{aF-1o atexecrOap-1lt{e}ifAc}{1.0w L/al/ grmv gswx xm1 x-1b10 cp1cmsqrt0.5 ppe cvenp11o acsc1274def}bindape8ixst}{1.0321.6als21 dict0pradeqd/a parcn counttomark{bs 2.2 16sl xmv2 n/dys 1 dp acInc.stsm 1.5 e 1gral39dv roundDA}{180s/wxpp AA}{1mv mvpp 12 0.6 DLBDA}{cwrotDA}{dLlWrev{neg}if0 g/wb0 sm stlZLBmx peq{dL}ifpgoacexec}b/CS{plpm 2mv .2 cp1 py bd DA}{dLdv l0p 0 apx 12L/l/linetodvmv2701.6gr}b/OB{/bS 1def/L{loadOA}{1 gsm rOx 0np o 0CA vm5sl n/ex ppyp m chemdict mvscal eq{DB}{DS}ie cp wppst}]epwo 3DT}]ocmL/n/negng/cYsme sl apwF 9.6 o 3.375 dpscradlt{-1 3 p gsLB pyr6 xcW np sm n g270cprO cp px px S}if/lp360sg cXppn2.25 ac10oL/p {80 wyn-1 end}b/Db{bs{dp ac2.25 SA sg0p fill l 0 gsst}{Asc gi10.4OA}{1ro}ie}b/AA{npcY0cmgr}{dpat pxn p 8np 0-9.6n/ey px 6 -1 sm 3 OB 2 sc gr 0 grmv mv0 smfill 4S nppy 14lW gs 1 olarc18gr mcvi/nSq s0 c Laser 1987,eq{DD}{DS}ieneg est}{0 m fill p bs SAlW dup2 gsend 0.5 pp1pp-2xdv-1 2CA DA}{120 pgr }{gs st}{0 1.2 m/w a}ie}b/WW{gs wD L/mt/matrixls st0 SA px pp cp sc ix 2 12-1p mv120n bb0 0 -1 stl2.25 ac L/ie/ifelse dxp lp neg}if/px DA}{cwrO aceq{gs bd 4 1 L/m/mul xl dx px9.6 sgx npiXp 012 1l neg}if/py 1py180-.6 L/ix/index rOp CAeq{dp g 2 sm st}{px a/py dp a lp n 3 ls{nH0e 1 r o rlineto e np ac0.3 Cambridge DLB gs 90 CBp lp gr sm sl m py lt{ppx 0 ZLB0acx aLpyL/np/newpath fill l p mlsgdp bdp -1 a}ie}b/BW{wD 0.5 setgray WIcm e rad 0 dv sg0 r g LBx scscdyrO ex gr-1 dv mt2 0 st}{Asc 1 px mv sc OB/bL ro p dv}{bd}ie 25.8 xl}{xlbW at OA}{1.5 -1 1.5 SA l x/dx g wF begin23 1 1 DA}{2.25 gs 2 m p p dv/bd mv CA fill 1 gs dp/cY d/WI{wx -0.41 w lW xl cm 3 o lp

Problem 2.17

Construct molecular models for each of the Fischer projections shown below. (Use different-colored spheres to represent the different halogens.) Compare the models. Is it possible to rotate the models in space so that they look identical? What is necessary to make the models identical? What conclusions can you draw about possible isomeric 089 6020 4480] forms of 4480 DSt SP 7 I 4000 4000 DSt [5 6 I 3520 4480 DSt Db 80 6960 4980] Ichemdict begin [4 4480 45 19 4000] 4000 6500 20 6020 bromochlorofluoroiodomethane? 4460 3520 4000 6500 4000] 48 DSt [1 2 megsst}b/HA{lW-121.6x-8pyn/dxarcdy12.2-1.sg0lrlineto2pp}{2AA}{1cptscl2180a/pxcurrentmatrixs/wylsgarc4 wcmat090ixfillngr0cmlcpt2xlne{bW-1oraccwe-2cXsbswxpxmdivL/mv/movetomscpyg/cX6x4lpwrr-1cm16.8bdgragppys mdictpxaRcvatl8dpero0.bs8s0ScientificCBl16opylpcmcp016clippathl4025.8cmr}ifwxm/aLdef}b/d/defsdpfillsm9.6cXd B1986,lpbW10SAmpCA180m0204-4.8 neglp rObeginppcmcm 0lpytrdp1rOsetdash}d/cRo/cXne{pydvxldpcv4dxbsl0 bdclip}b/Ct{bspxmvsmsc pysc5r0gi0dv/bdpxOA}{1pcm3nexor{4mvr0lWcvwbrad-0.4gr}ie}b/Cr{0x360pmvopy s pOA}{11pydictpputbWaAnpg 360parc0 Computing, 1sc}b/Ov{OrAstSgrsetgray0BdnHscpxd/wFdvwL/a/addx180 p negOBroPrepnegl}fortr/dyscmpx01180sg dvenparcocY lpm 1bsgi1alacggsx}if24.6AA}{1gi01sm0st}{0pxlWOA}e dLp2l0fillrSAradmrotpy.stm}b/dA{[3dpwSAfillnp[{py-1pymt2ro4.82g/bb-12scg px1-1gr}b/wDfillmvDSsppSAOv}{ FalaL16.8graLxne{bW012gr}{gs x20.6 acpx0xr-1.6dp5l0ene{bWgrfillDA}{27043SA9.6pAc}{0.51.50d/aFpxcmx D yL/gs/gsave 0eyrO0ac dpe 5180type[]type x}iflxalye wpp}ifelseplwySAdvgr}b/In{pxgrwbe5paRradpxgsnpstslm atL/xl/translate L/S{sfOA}{1 begin/version wy1def/b{bindbL put0ppac ssm}b/CB{np[{[{CS}{CS}{cB}{CW a}{ex1458sc0120 1gacpy 24.6-1 spy S]}b/dL{dAcm gspppxfill}b/SA{aF-1o atexecrOap-1lt{e}ifAc}{1.0w L/al/ grmv gswx xm1 x-1b10 cp1cmsqrt0.5 ppe cv 16ne1o acsc1274def}bindape8ixst}{1.0321.6als21 dict0pradeqd/a parcn counttomark{bs 2.2 16sl xmv2 n/dys0dvmv2701.6gr}b/OB{/bS 1def/L{loadOA}{1 gsm rOx AA}{1mv mvpp 12 0.6 DLBDA}{cwrotDA}{dLlWrev{neg}if0 g/wb0 1.5 e 1gral39dv roundDA}{180s/wxpp 0np m 2mv .2 cp1 py bd DA}{dLdv l0p 0 apx 12L/l/lineto0pnp sm n sm sm stlZLBmx peq{dL}ifpgoacexec}b/CS{plpo 0CA vm5sl n/ex ppyp m chemdict mvscal eq{DB}{DS}ie cp wppst}]epwo 3DT}]ocmL/n/negng/cYsme sl apwF 9.6 o 3.375 dpscradlt{-1 3 p gsLB pyr6 xcW fill Inc.stg270cprO cp px px S}if/lp360sg cXppn2.25 ac10oL/p {80 wyn-1 end}b/Db{bs{dp ac2.25 SA sg dp acl 0 gsst}{Asc gi10.4OA}{1ro}ie}b/AA{npcY0cmgr}{dpat pxn p 8np 0-9.6n/ey px 6 -1 sm 3 OB 2 sc gr 0 grmv mv0 smfill 4S nppy 14lW gs 1 olarc18gr mcvi/nSq s0 c Laser 1987,eq{DD}{DS}ieneg est}{0 m fill p bs SAlW dup2 gsend 0.5 pp1pp-2xdv-1 2CA DA}{120 pgr }{gs st}{0 1.2 m/w a}ie}b/WW{gs wD . L/mt/matrixls st0 SA px pp cp sc ix 2 12-1p mv120n bb0 0 -1 stl2.25 ac L/ie/ifelse dxp lp neg}if/px DA}{cwrO aceq{gs bd 4 1 L/m/mul xl dx px9.6 sgx npiXp 012 1l neg}if/py 1py180-.6 L/ix/index rOp CAeq{dp g 2 sm st}{px a/py dp a lp n 3 ls{nH0e 1 r o rlineto e np ac0.3 Cambridge DLB gs 90 CBp1 lp gr sm sl m py lt{ppx 0 ZLB0acx aLpyL/np/newpath fill l p mlsgdp bdp -1 a}ie}b/BW{wD 0.5 setgray WIcm e rad 0 dv sg0 r g LBx scscdyrO ex gr-1 dv mt2 0 st}{Asc 1 px mv sc OB/bL ro p dv}{bd}ie 25.8 xl}{xlbW at OA}{1.5 -1 1.5 SA l x/dx g wF begin23 1 1 DA}{2.25 gs 2 m p p dv/bd mv CA fill 1 gs dp/cY d/WI{wx -0.41 w lW xl cm 3 o lp :l C : : I : . . . . . . . . : I B r : : F C l : . . . . . . . . :. F : . (answer) :: B r . . currentpoint 192837465

Problem 2.18 Repeat Problem 2.17 for the two Fischer projections shown below. . . :l C : . . C l : . . :: B r . . . . : I : . . C l : . . :l C : . . currentpoint 192837465

. . : I . .

. . : B r . .

(answer) Additional Problems

Problem 2.19 Write structures for all molecules satisfying the following descriptions: a) an alkyne of formula C5H8

(answer) b) a carboxylic acid of formula C5H10O2

(answer) c) an alcohol of formula C6H14O

(answer) d) a compound of formula C5H10O containing a carbonyl group

(answer) e) a chloroalkane of formula C6H13Cl

(answer) f) a molecule of formula C4H10O that contains an ether functional group

(answer)

Problem 2.20 Give the IUPAC name for each of the following: a) CH3CH2C(CH3)3

(answer) b) CH3CH2CH(CH2CH3)C(CH3)2CH2CH3

(answer) c) CH3CH2C(CH2CH3)2CH(CH3)CH(CH2CH2CH3)2

(answer) d) CH3CH2CH2C(CH2CH2CH3)3

(answer) e) CH3CH2CH(CH3)CH(CH2CH3)CH2CH2CH3

(answer) f) CH3CH2CH2CH(CH[CH3]2)CH2CH2CH2CH3

(answer) g) CH3CH2CH(CH3)CH(CH2CH2CH3)CH2CH3

(answer) h) (CH3)2CHCH2CH2CH(CH3)2

(answer)

Problem 2.21 Classify all of the carbon atoms of the compounds in Problem 2.20 as primary, secondary, tertiary or quaternary. (answer)

Problem 2.22 Provide IUPAC names for: a) an alkane that has the formula C5H12 and contains only primary hydrogens

(answer) b) all isomers of C8H18 that do not contain any secondary hydrogens

(answer)

Problem 2.23 Provide IUPAC names for each of the following: a) neopentyl chloride

(answer) b) isohexyl bromide

(answer)

c)

isohexane

(answer) d) sec-butyl bromide

(answer) e) t-butyl bromide

(answer)

Problem 2.24 Each of the following is an incorrect attempt at constructing an IUPAC name. Explain what is wrong, draw the intended structure, and provide a correct IUPAC name for each. a) 4,4-dimethylhexane

(answer) b) 2,2-diethylpentane

(answer) c) 2-sec-butyloctane

(answer) d) 7-ethyl-2-methyloctane

(answer) e) 3-propylhexane

(answer) f) 5-(2,2-dimethylbutyl)-3-ethyldecane

(answer)

gr 35I 2 2020 1991 2020] ]d end 1 1160 2545 1560 1560] [1 [01714 1720 1714 1560] /bs[[1 57 1560 45 1437 chemdict 2545 SP 72 1 143777 4 172019 1720] [5 I 6 begin 2200 DSt Db 2268 1991 3 48 2268 2200] 2545 20 DSt Problem 2.25 x ix 2 rOCA nppxn ac L/ie/ifelse py 6 m ac sc pyrev{neg}if 0 l0 cm py st0 0 ac dp 180 r 21 In DA}{cw wy m2a}b/PT{8gr1 lst}{0 eq{DD}{DS}ie gs 2.25n/dy np[{py 0 SA sm 42r 4 lt{ppg px lWxlapg a -1 -1 dplp 5 bW s mv mv 0 o counttomark{bscp24.6 smo gseq{DB}{DS}ie 3 wbs SA1p 39 o radS}if/lp LB o g 0 cm -1LBL/gs/gsave -9.6p chemdict type[]typep rpp 0bW 16ne L/mv/moveto py py 0 9.6 12 e -1o scg b2 at neg}if/py dp DA}{cw 0ScientificwF 2 m l16 arcInc. mt x l e put S gsp px ppg/cX x4s fill1 pp}{sqrt p n 16.80.3 py m CA l m}b/dA{[3 CBr lp scW0mv e at ppp}{2 e algr cm -0.4 ro}ie}b/AA gs pApxdvnp st cpp 90-1 08 0 m/w dp DLB -1 1 dv/bd cvbeginl0gs lpsm1.5 01g/bb x sm}b/CB{np[{ np fill psm0 n neg atn/ex n m n/ey px m a04 2dy w16dv 0-1.6 osc}b/Ov{OrA1rOw-13 at24.6 nH o-1 cp 8p mv-.6wFpx2lwy aRcvpm1rotac 0-8rot scgs120S]}b/dL{dA1275021l 270trmvacalsetdash}d/cROA} py sc 180 execll lmvgsPrepneg-1mv bs8py360rarcst}{0 -1 OA}{1cm ecmfill}b/SA{aFx dv roundDA}{1 dpp2 -2m sm pOA}{1np atl p cmpy0 xlgr}{gs -10.5Computing,1ocYscmv4pp1lgs pxm x}ifsg a/pxo/cX -8py -9.6xWI1.2ppOB81ix xDLBm 1sma}ie}b/BW{wDCBxl}{xl0 dpcmst}{Asc2rad1setgray 4CA AA}{1 st}b/OrA{py51mst}b/HA{lWputl gac0L/ix/index0 neg 0.5x}if0cmrOgacgr}b/OB{/bSnp scDT}]o pgr}ie} -1cwl mdv120-9.62.25bW end}b/Db{bs{dp begin/versionL/mt/matrix27dupZLB-1px def/L{loadcurre RA}{6dp negbdclip}b/Ct{bsdp20dv12dv}{bd}iealp2.2sgedprlinetoclippathstbd DA}{2701m/aLpdef SACopyRighta}{ex120.601ne{bW 18001n/dxarcL/l/linetoDA}{2.25smlWsmst}]elWcvOA}{1 nacxdv l dp/cYHA}{dLaLslfillrwx rad120pbW2a}ie}b/WW{gs2 fill0fillagrgracWIeq{gsrO25.8g0 eL/m/mulrO3lpx ppChemDraweLasersgdvscxpyL/S{sfscsscppxneg}if/pxo0sglxnpppmvcm 10st}{pxendo0.52execgs 61aL 0wdprlt{1pyp scarcnpygr 1DA}{dLtr/dypy lp 5slLBracpp pxcXlpbssmg/wbpor{4lfillcpa/pyr}if0scw gr}b/w xl 2cmmvscstpmvexmropyaL1.2rO0b1xOA}{1mvgi18016SA1dv fill pp-11.600OA}{1.50.4 gr}b/In{px360e L/tr/transform1986,acSAdictscl}for1.5eSA16sqrtrO90SArOxgrnecpwgsne{bWAA}{1SAm 8wx-0.40gr1cm L/gr/grestoregrL/xl/translatep180paAnp30-1pxsmvOBl1begin23wxpx2cps2smlgiwy0pp1ppleq{dL}if2xAc} userdict/chemdict0145fill0grpx-1cptstst}{AscxxpylWsgpxDA}{cwsmmgslstpgrpygrScpt 1cpxlZLB SAgdxlp %0gr 20s{dppyegs0mv1987,0mtxro0lt{-1ne{bW0e3dpcw1-2eq{dpdef/b{bind0def}bind 2sdvst}{1.03aco dvgr}{pp}{gs lp bd ey e 0 2.2180 p 0.6 ace pywylp bsst m rocp fill dv mv 3 ix -2 gs 1 dv neg p mv px Cambridge x/dx -4.8 25.8 x setgraypy div m dp ap wb a 1 sc -1 p exec}{al 5 -13.375 SA rad dx5 g 0 pp dp bd 0 -1 p g 2 ro sc OB/bL 21.6 8 -.6 cm p neg l DA}{dL wD np1 1 CA cm 2 m sc s ly pp}ifelse dv/bd x lW 4 fill L/n/n ac n px0 bL gi 4.8 sc Bd ix 0 cm -1 1 lp 0 pp w sg l Provide molecular formulas and IUPAC names for the compounds represented by the following skeletal structures: a)

currentpoint 192837465 gr 48I ]d end1 1160 1720 1437 chemdict begin SP [1 [01714 1720 1991 1260] /bs[[1 575 1560 1714 1560] 58 1 143757 48 45 19 1720] I 3 2268 1720 DSt [4 I 1437 1260 DSt [6 I 1991 1260 DSt Db 1991 1714 2268 2060] 1437 DSt 1560] 2060 20 [2

x p -1 dplp In DA}{cwLB p 1 ro px lmtx glt{-1 6 2 wy m2dv b2 e np l n dp xpym CA py0 sc a bW 2 mv n 1gs p 12dv 1ne{bW 2m}b/dA{[3 py 0.5 lp ly 0 mvmtL/mv/moveto dp 1 -1p apgs 5 g-1 s HA}{dLn 16.8bd m1 m/w bsst}{Asc-1ost}{0 sc16fill grcm lsrosm1gs -1np x rad g/cX curren o -1o mv negpm sl lp ac dp 180p0l L/ix/index0r S]}b/dL{dAwx cY cm or{4rOcp0.4 scix 1m/aL 360 c e 10 psm0 mvarcn counttomark{bs-8 24.6 sm0.6 eq{DB}{DS}ie lplW dupbd p px 0.5 ZLB 0 p aL p fill pp}{sqrt st mv 900.3 L/ie/ifelsepx 3cm ac 1rO 2.2 py00np 1 gs 3 cml4 0 2ZLB gs e g execn scdv r2 gs pAscg smbdcpo n/ex DLBl}foraAcp5n/dxarcdy n/dyx}if23grl 0at 2 1270p lfill a/py wb px 0 nHdef}b np fill pxdvnp-9.6 lwysg0.601.2L/S{sfOA}{1 r0 mv1cw xOA}{1psmp divstbL fill1 pxapdvatst}{1.0 Ac}{ cp 8ix180 execlm2.25r py atey rO0dv12 pylp sl0pylWsg cvL/mt/matrixeq{gsst}]e setdash}d/cR3 l-1 p py sc mv 120sclL/xl/translatepn/eytr/dy0x/dxtype[]typeseq{dp pcmscsm0st}{px0SA0sc8240-0.4 26x21.6 dpCopyRightat l5atgs SAxn m mrosmxlsm 16gs eL/l/linetoxrfill 0dpwpyst}{Ascdp 1lWcvsm}b/CB{np[{[ -8py mdvnega}{ex1458scSA-121.6dpgr}{gsx12alpace sgbegin osc}b/Ov{OrA2 pp1xgr}b/In{pxgrac -1 st}b/OrA{pypeLaseracgr rad120pbW0scrot -1 -1xsc CBr lp rOnp[{pypxacm2smgr0alr end-1oDT}]ofillr-212exr -1cw -2s{dp pgraL00pyix 1DA}{dLchemdict begin/versiongralpdef/b{bindcp41gigr m OA}{11 DA}{18g RA}{6a}b/PT{8neg}if/pynegrot10aca}ie}b/BW{wD CBmsg 0cmrO02cppOA}{1.54cpt1L/m/mul0xlOA}{1 SAChemDrawpx0st}b/HA{lWputpy1.5ppy m 4pgi0dpwl6 filledpmv2701.6pxwp4.8lrad4 392sscround9.61wbx5 l dp/cYm WIpy1986,81987,gr0cm b1xa}ie}b/WW{gsrev{neg}ifeog/wbmvbs put rOcmr}if0pp lWgsxo4war ppdprlt{1pyp5mvppfillnpfill00Cambridgescp pxs23acpp1-1cXpbs1smpp}ifelse ewyDA}{270sc w gr}b/wD 0wp2l-9.6-.6wFOA}{1aRcvp-9.6DA}{cwne{bWarc09016dv0wyarcbs0WIgr}b/OB{/bSdvdef/L{loadgxgLBlt xl 0gr2exec}{alclip}b/Ct{bspx-1lac180SA360neg}if/pxpxDA}{2.25stcm1smpSA0aclt{pplWsg1SAgr}ie}b L/tr/transformL/gs/gsaveend}b/Db{bs{dp mv2.251SAoxl}{xlacInc.mgsl01.5lstst1Salgxpx}if180pprOdxo d/ L/gr/grestorenegOB3.3750eq{DD}{DS}ie0sqrt0.5Computing,pp5neSA0fill}b/SA{aFomeq{dL}ifac3pxe1 userdict/chemdictpx1-1 dict dpmv-.60np10apx-4.8dv/bd-21dvnecp-1gspp}{2gimv0Ssetgraypya/pxo/cXne %2cmcmscst1.2pexmvwxaLpysce0cptstdxDLB5gsLBneg2pxcWlprlinetoclippathAA}{1wpp3dv24.6AA}{1gi0 dv0 rO 1 dp -1 p gr}{pp}{gs st}{0 8 p -1 2.2 g x CA gr-1 Prep bd rad 2 m bW sc p 2 ro OB/bL 8 g DA}{dL 1 DA}{cw ac p 27m py dv}{bd}ie OB wD setgray ne{bW g/bb -1 px a cm e 180 ScientificwF CA0 -1.6 g nex py 25.8ac mv 4 ix L/n/neg p neg 180 SAp lx 1 l gs 2 2 m 25.8 begincmbW 16sm etr gr np 0 l s def}bind py ro}ie}b/AA{ dv/bd cp S}if/lp cm l xl 3 lp -0.4Bd0 wx CA -1 l lp sg s{n (answer) b) B r gr end 2 2260 2528 2200] ]d 1 1974 2200 2251 1420] [1 [01697 1860 1974 1700] /bs[[1 1 1420 48 451697 1700] 101 53 70 1700 12 13 1860] 2260 DStbegin SP9 3380 2320 DSt [6 I 3359 1700 DSt [7 I 1697 1420 DSt 2220 3082 2805 70 1860 19 20 chemdict [4 I 5 8 2528 3 10 3082 2260] 2251 2420 2805 2320] I 1920 2220 3380 1920 1697 currentpoint 192837465 3359 2420] (answer) c)

x 2 cm sm p p 8bW py p0dv L/ix/index3 wF CBDA}{2.25 m bsgil 25.8 1p 0.5 4 lp 2 11LB 9.6 In DA}{cw wy m2gr}{pp}{gs l 1 0.3 ey x-1ac a}ie}b/BW{wDr begincm gs mvdupbd Scpt dp sgix n opx 0cXm a -1 -1 dv st neg}if/py xm L/S{sf p p lg 5 bW 2s{dpLBe ln 16.8ac 01.2 m lcpta}ie}b/WW{gssg 0begin Inc. gp sm mv px ppe round0acxdv pxnL/n o g0 mv b2pmv wysgdpDA}{dL0 px g 2 parc pyl SAeq{dp0 bs pcm 0m st}]eg acpywx SAgr}b/wD-1dv e -1ix s dv 0 pnegOBac0.6 -9.6m/w 0 2.2 -1 neg}if/px py -1.6 o ac ne{bW stradlt{ppsm}b/CB{np[{[{CS} fill pp}{sqrt1.2mv st}{0negn/ey dpe 6 lp sm0 CB lp sg np wx 0 2pst}{Asc g/bb xdef/L{load 3g aLx1dp/ gs2gr pxx negpx0st}b/HA{lWrotCAstcp3 p gs e algs 2 sc lxne p g elpcm4 def}bindodv xl st}{1.0x-1lt{e}if np fill scdvnp-9.6at 90bd end}b/Db{bs{dp ac2.25cw cv dvmv270mpp}{2 dp rppgs scixa a/px pac d/wF cp 8p 180120bdcp1 pygr atgr rOpy bsnpDLB4 gi 0.5ac filllps0 0sm gscp 1.5 SAgral -1 scp sclW9.612wr5mv py sc m mv npe clip}b/Ct{bsscebWx0dx0 apxarcdv/bd xcW23pdef/b{bindsm 1140.4 -1x g 1ro}ie}b/AA{nps dpCopyRightgraL0 lpwx p0l8dpmvp180 24.6type[]type x}iflp aclpg/wbsl or{4fill00ppxsc2 4CA DA}{180p0ed -81pA-2g negatL/xl/translate-1rogtr/dy1 scmvpy OB6 -2OA}{1grmvsm wcp2alSendOA}{1g/cX currentma st}b/OrA{pyscLasern-1 xDLBDA}{cw scmsqrtdy1n/dym 16arlineto3eq{gs epycp439gr}b/In{px scl -1pals23 -10cmpsmexecL/gs/gsave dppxrad-112py0DA}{dLS]}b/dL{dAcm 5pp}ifelsel4wyrOcmeq{dL}ifp o/cXarcsc1 RA}{6a}b/PT{8expx1987,L/ie/ifelsexlne{bWx20.61rev{neg}ifppatSAlWlst4.80ZLBsetdash}d/cRx3lpne{pyg SApp mvscst5pmpp 145 sc1ppcmb1aA8spy16-101st}{0 rOsg0 111 wnacpxL/mv/movetomscS}if/lpgdxs{nH181 l py 20HA}{dLgso counttomark{bsscmn/dxgsmv25.8oDA}{cw cmscgr}b/OB{/bSdvwbatpp1ppL/n/negfillcY ppdp-9.6-.6mvmnp 12ixfillm1m21.62py5180sl-1odpw16dvnp[{py pxstne 0pygr2dv/bdxx}if 180cm6grAc}{0.51 0wChemDrawOA}{1aR810eq{DD}{DS}ienegssc 0Computing,0rOpydiv10ptrput DA}{270pxm/aLdef}b/d/de xl cwlrlt{1 WIpy1986,roSAaLSAput1chemdict0begin/versiondplarco16clippathrOgsgrsetgray0BdAA}{1lsg2sm0 L/tr/transformlarcngspydictbd180ac-8rot360-4.8 lW2.2-10rwylydp-1WIsmfill}b/SA{aF2r}if24.6fillOA}{1rs/wx L/gr/grestorea}{exn/ex radne{bW0lOA}{1 5r012rnegwDxl}{xlcp0cmmt2roe0p1lgi1SAapomvexecrOapgs-1gscm userdict/chemdictfillrPreppy0l}for1.5m}b/dA{[3L/l/linetoegrfillesc}b/Ov{OrAstac-1np3-0.41-0.4gr}ie}b/Cr{ %dp/cYmpywF1lp2lsl03.375n0Cambridge0cmpxxLBacppepx10setgray1.61270pAA}{1wcvpx0py10nH360exec}b 1 dp CA 2.25 px 120p 0 st}{Asc rO SA scX np sm ls st}{px a/py dv ZLB xl 4o e CA o dv -1 dvexec}{al 5 m np dp rO lp grmv dv mt 2 sm dv}{bd}ie p eq{DB}{DS}ie 0 bL -1 OB/bL 1 sc ro cv lt{-1 x/dx -.6 gr}{gs 180 pxp fill bW l SA Scientific90 CAx pbsgr cY x 2 0.5 L/mt/matrix27 2 1 m OA}{1.5 lW0 L/m/mulgs 21.6 g/c m1 l rad -1 r wbpy aR 8lW w -2 cm pp DT}]o 3 gi m

gr end 2 2260 2805 2260] ]d [01974 2480 2528 1400] [1 1 1697 1860 2251 1700] currentpoint 192837465 /bs[[1 1 1420 48 451697 1700] 100 57 70 1700 197481860] 2480 DSt [4 I 5 6 3359 1700 DSt [7 I 2251 1400 DSt Db 2220 1560 3082 2805 69 10 11 2528 3 9 1860 191560 2251 2420 3082 2420] I 2220 1920 3359 20 chemdict begin SP (answer) d)

x 2 2s{dp In DA}{cw wy m2gr}{pp}{gspx1 0.3 gr L/S{sf L/ix/indexrO ac eq{dpcp gs st}{Asc ZLB np0.5 4 -1 n x21.6 9.6 a -1 cm b2 e neg}if/py 1.2 x-1dv px DLB neg}if/px py np wx 16 sm 04.8 radlt{ppsm}b/CB{np[{[{CS} 5 bW -1 x -1 1.2ln p st}{0 xpsce0ac a}ie}b/BW{wDeq{DB}{DS}ie cp sm l 1 0.4 p dp st}{1.012 0cXm o g0 s dv negpx0 16.80.6 DLBDA}{cw 6 2 gs sc S]}b/dL{dA0 g ne{bW bd px ace round9.6xl aLx1dp/c e -1ix psm0 LBe cp1 90ac 0-9.6m/w 0 8 0 16sme CB CBDA}{2.25 ac p dupst}]eg pppywx 1 0ac1px pxfill fill pp}{sqrtpmvst}b/HA{lWrO lcpt12ne{bW arc pyr begin23cm 5 2cm 0m SAgrSAapscixaro}ie}b/AA{nps gs1gr pxrO pnegOBacbd DA}{dLchemdict sl-1 3OB 2 sg -1.6 pg/wbsl wpgimvDA}{270 execrOodv d/wFcY np pA180execL/gs/gsave dppn/ey dpdv}{bd}ieL/l/lineto lxne bs gsgcm4sm al00p xdv g sca/px pg -1pr mvg cp 8p scdvnpp1Lasern-1 end}b/Db{bs{dp -101dpw SAsc 0setgrayWImv1.5 stg/bb gs scp 11lW0r apgs-1gspp py sc m mv nbdmv 145 atey rotpy x02.2 p0begin/versionps0 p p-1e3eq{gs dp14Sm0 3DT}]o DA}{180-1m dpCopyRightgraL0 pygr xnegcmb1bsnpg apxx2.25cw filllwy aclInc.pmt270def}bindcveq{dL}ifp 3acwr5p0ed -80fill-2g negatL/xl/translatempCAstm}b/dA{[3algs lp cv16mvocmlppxfill}b/SA{aF-1x xlS}if/lp sc-1lt{e}if st}b/OrA{pysclppwysgdpp0l8dpmvp180 3 lp 4arcst}{0 xcWcmdpw1.61xor{4fillSendOA}{1BdAA}{1lsg2sm1 -1py mv 120-9.6at lpbWsc1pymbWaAps5 mmvpylW2.2x}iflp rlinetoscgr}b/OB{/bS-1 px0py-0.4 currentma RA}{6a}b/PT{82lo counttomark{bscppy-1sqrtdy1n/dym rdpfill 270msmroetrputrppdvwbradm/aLdef}b/d/de SApp 20HA}{dLgsslfillrSA1neq{DD}{DS}ienegsmv25.8 -2begin smpp}ifelse 2wyrO39x}if 4CApp o/cXarcsc1 l cwlrlt{1 WIpy1986,ropyaLSA-121.62xlpy0DA}{dLwF 6 dvsg0 111pxstpp}{2 lrOgsgrsetdash}d/cRx3Ac}{0.5 ppdp-9.6-.6mvmpp 12ixfillm1put1gtr/dy1180ac20.61l16rOnp[{py0acSAlWlstpAA}{1wodef/L{loadL/n/negnL/n 0wChemDrawOA}{11987,L/ie/ifelsescmn/dxpgiodv/bd -10efillllydef/b{bindcpepycp4cmomvppSAgr}b/wDs/wx xl 2cmmvscst5pm2.25aR8dictbd180acpyscsc5r012r0Computing,egrmvne L/mv/movetomscpx10nH360exec}b L/tr/transformlarcngsPreppy0l}for1.5dx24.6type[]typepx1dvaarco0pydiv0pygr0dv/bdxgr}b/In{pxgdxs{nHg/cr L/gr/grestorea}{exn/ex radne{bW0la}ie}b/WW{gsrev{neg}if0sc}b/Ov{OrAstac-112r}if180cm6grlpne{py0 userdict/chemdict03.37500Cambridge0cmpxxLBnegwDxl}{xl0ppcYclippath4225.8pxsc2 24.6fillgr}ie}b/Cr{ %dp/cYmpywFstclip}b/Ct{bspxrad-.6-8rot360-4.8acppeoDA}{cwrOn2pm 1bs0p1lgi1alsetgray0g/cXOA}{1als231 1 dp lp o dv sm ex l np dvexec}{al 5 m8wx dp dv CA np grmv dv m p 0 OA}{1 gs0 p SA 0OA}{1 cm ls st}{px a/py L/m/mul2 4o py 18 -1 px 120ro sm st}{Asc 180sg scX bsbW l 1 OB/bL 2 lt{-1 p lg sc mt 0 e Scientific90 m p gr gr at 0 bL ro cv -1 gr}{gs 0.5 2 x L/mt/matrix27 SA x/dx 2 px pnp sm 2 1 CA 0.5 OA}{1.5 lW1 dv sgix xl 1LB CA cpt l at 3 lp gs wbe aR 8lW w -2 cm cm -0.4 ZLB gi dv

currentpoint 192837465 (answer) e)

currentpoint 192837465

currentpoint 192837465 (answer)

Problem 2.26 Show skeletal representations for each of the following: a) 3-ethyl-4-methylhexane

(answer) b) 2,3-dimethylpentane

(answer) c) 3-isopropyl-2,2-dimethylhexane

(answer) d) 2,2,3,4-tetramethylpentane

(answer) e) neopentyl alcohol

(answer) f) the smallest possible amine that has three different alkyl groups attached to nitrogen (answer)

Problem 2.27 Draw Newman projections for conformations of 1-chloro-2-iodoethane in which:

a)

Cl and I are eclipsed with each other

(answer) b) Cl and I are eclipsed with hydrogens

(answer) c) Cl and I are as far apart as possible

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Problem 2.28 Draw a Newman projection of a conformation of 2-bromo-1-chloropropane (viewing along the carbon-carbon bond between the first and second carbon atoms) in which the two halogens are as far apart as possible. (answer)

Problem 2.29 Give IUPAC names for the compounds represented by each of the following Newman projections: a) C (C 3 )2 H H H H

H C 3 H (answer) b)

H currentpoint 192837465

C3 H HC 3 B r

B r C 2C 2CC H H HH (
3)2currentpoint

192837465

(answer) c) H B r C 3 H H C 3 H (answer) H currentpoint 192837465

Problem 2.30 Represent each of the compounds in Problem 2.29 with a skeletal structure. (answer)

Problem 2.31 Use a set of molecular models to construct the butane molecule. Once constructed, rotate one of the carbon atoms connected by the central carbon-carbon bond. Consider the two conformations in which the distance from carbon-1 to carbon-4 are greatest and least. What is the (approximate) ratio of these distances. (answer)