(0) The lf sido and he sgh sid night have doable Bonds a immediate prcarors the Fete se may etl few a Simmons-Seithcabenoid ali to an kee and elt ‘Stay oat! om hyatcn ofa akee. Lets stat wh Sebomo- proper 8.17” sno posible form a small ing containing tiple band because the angler that ‘wouidresut from bending the bonds ofan sp-ybridized carbon to form a tml gis too pen Additional Problems 5.18 5 © @ ® crore monet nye congo =0OHso, 2.2-Dimethyt-3chenyne 2.5-Ocladiyne © @ 3.6-Dimetbyl-2hepten-t-yne —_3,3-Dimethyl-1,S-hexadiyne © © iibethd rscHepHCSCOHRHC, roy Oty Hyo=onoH=cHo= 1,3-HexadienAugnes: An Tntodustion $0 Organic Synthesis 168 819 o gH oyosoosobioncnozon Heo S-Ethyl-methylt 68-decatrhyme ° @ ld paosedy ne ‘poms ‘rong 2.2,5.6-Tetramethyl-3-hexyne 3,4-Dimethyleyelodeeyne © enon =cHoHmOHC=H -Heptadien-I-yne oH. pean 3.Chloro-4,4-dimethyl-1-nonen a) crags . cr oHoHrnoHC=OH Sesee-Butyt-I-heptyDe S.ter-Butyl-2-m 20. (6) CHyCH=CHC=CC=CCH=CHCH=CHCH=CHs, 1,3 8,11-Tridecatetraen-7,9-diyne Vaing £-Z notation: (ESE. IE)-13.5,A1-Tridecaetraen-79-diyne ‘The parent alkune 0f this hydrocarbon is indecane. _ ) cuscece {C=CC=CCH=CH3. I-Tridecen-35,7.9,11-pentayne ‘Thishydrwenrhom sito belongs to the eidecte fal. ae cy or 8.21m0 822 8.23 8.24 chapter (0 Any ane ih pt cuba atte ola i: Cai has cl ver ‘Sugars, or four ewer pio ydropens han Cyl The elcome our Spetichadanmace repeat ott oy tee ciated techs Beavis co Poses ote bated wen eurten dere van csi Re nada Rc a aa Pais oar co Gila ese S sepmaicenee ene or “ woman on oe o ® cnonoroueson TSB. cncnscrycnye ct, » OHCs 8 owowayowomen Sat. ed oh « au, g emorcrsoncmon AES crgcnycrcngrcry 6 2 cryonteats pL OH CHIME COH CO —Trgar * satay oeAnynes: Am Intructon t Orgiie Synthesis 171 Ciiyrg_e=OICHog Ae ° CHOC} e WO onccaoce io mole pr cayonyescimytry HE eed © oumne=aeiaens TEM oyoucnaouiooneol ° oe t foHgyo=O eyo TATE te CmOHy OH coHCHACHECH ONO . roe He crserne=ciool crete 8.28 EU cHycHoHscIm teem, is Choe COE pe er ae ae oy EE CCH CH CIEIOHCy - + CHCH,CH,CH,CIBrCHy Y0HCo iy @ i ery EH CCH COC + nyonengcrstory 1.0. He$04 oe HGS0,,a2 Chapter # 5.26 a a iG vie ‘2. dn, Hy0™ a J as.ony 6 [eon PMH \ sama 2. CHyer ® HzO. Hy804 a HgSOg ae 827 019504 i Cac bios st ebig THE Tie OF c= Cety 4. Na Ny, 2 cig erigoHcHcHOAaltgnes: Aw nicueton to Organic Sputesie 173 © * cor fx cxcoy %y ‘Tra eaar om ramon oy : TET ENON + COs o . CH joH OME CHLCH= CH ar cocina Ht ‘ ie OgcHoHOHC=CH a9 @ npr ete. wate cr trans-S-Decene W E ry He = ween Thos cle $-Decene ae ® i 8, ae. & ek Deceme O [ere whe et Nee EE trans-5-Decenene 8.30 8.31 hapee Bath KMnO4 and Os oxidtion of slyes yield carboxylic ce: emia! akynes ive Coy isnt (2), ed () the cbserved products cn also be formed by Kin, ‘nition of he comesponding alkenes © tyre a — aM Soe © = AOL nectar Soe ony one cleavage products formed, te part hydrocarbon must have contin 2 {ipl bead ss pa of ang. HoH > CO, ) © cvprbonaye=or 1 tcare anon + aula +t [Nate athe procs ofthis ozonolysis contain aldehyde and Ketone fenton groups, aswellasa cabonyic aid and CO, The pve hydrocarbon must hus conan udeue ndatiple bond o . wo. fl 3 ee onosonendion + 00 @ cryougensc oH He cHyoryoncHm cy OB oycHsch,cho rane a os MAID. yen =con une KT fretsAmynest Ae Intrducion to Organic Synthesis 175 8.32, Stratogys The pric contin ai-cisbaiued ng. which ca Senet Toms Gnmors Sah wast of Chay wih ace ale fh tone ih acs ‘nda be prod rom ar alae by hylopsaten ving a Linder ealy.The eed ale en be fooed fm the Set tata shown bya alain in Sesnometane. [Soe ony as crorectittl, “Oy = FEE cycle “oly 433 4 by down coxa fe, Oe ae OF han Gr srs 2. Hebe, OH f oe. OR OM OF 1. Nah Ney 2. cHyBr oreo ‘The rae du ond in ere eles pected of al and with Ltn NEy The alkyne was formed by a allylation ef termal ale wth Fromomethane, The terial ekyze van sytesized fom Ue stating alkane by brominason, followed by achydrtalogenation195 Chapter 3 ee ° : ae eS a ee 8.35 Inallof ese problems, an acide fon (or an anion ofa txminal alkyne) is ayes by aka. © een tie . SOM a cagcHscHam Hae o sayy tee. Ni, cn 1 Na . a cuore es eouounrmsg ceca oHcH,cHycrycH,oHoAllynes: A Introduction to Organic Spathesis 177 8.36 8.37 ce 2 Natt ty HOEY prcHatcreoraee 1.38 Steategy: Musca s Cp alkene. The oly fenctionl group present isthe double Bond Setween Cs and Cio Since ur sys bps wih erlen, we ean ss at the duble hod an edie by Bydropertn ape Hand. Solution: 2. ay Mg 1. Neti Pononecrr a FORCE onsen