+ The n-bond of Olle has liken and tWo-new 6 bond dormech f+ YK = ona [ot Me Kee BC kei) = ga. eal a! t 7 vond energy s the 1D bond is such weaker than §- pond waking i much more casi bn : when. AS a indew: i ‘ a Ss ‘esutt, alkenes undergo + Generally © addition wepoetion fain of a c=< double bong Car botation/ onium intermediate Aikere For (ayslc.) ystem cc Terminal Alkene Lnterros Mkene . WS as a Cydloherere/ Gcloatuans Plleane For Cyclic Syston v Erdgoletinic System a ® Hycvotion of Atkene : Guus) 28, Addition of woter to yield Atcolls H26 deaf feo weak as acid to protomale om alkene, 0 Yeaclous 8 such %s wot possible. \ ee , Cone ek this reaction con procead in presenee: of" #1230 | Bot oof?) atea ~~ ——— ——— PD Trealmen) wilh Hy¢dq + Mkenes rare with cold, conconbated aos tom on covmpound of general formula Rover» Knows, as oly hydrejon cublate- p-f-on 2 yx Hg -f—on — hy | | 3 | wrote | hydreqen | teh 8 oat | * Bard carbon canter | nd e ford oxygen « is bonded 40 Io | 7 Resellon canbe searanthagh corned — | the reser veouteks fat’ conact fh two differ : fea) Gate of the olkenx Woys, dopend on the Phasiead | | | Alvene ie bubbled frto the ell. t i shivear oy <> xceous ~ [- a : = Cane 250. cE . Cnc: I 604 aa ol iB Atlee Unis) | The weehowitnn Ynvolves * the forwation of covtsestion vin the ee Cues oo | vi we O-¢ on ono 7 $ co Pit For] @ EY Crveverslae) ConlbotoHon ° o-F-oh | 4 | } Aleyi ae (+ Ale! Hyde tycrogein Gulfte, sett : | ada chee gs BOF as dal Sctea tel but Stuoion witiln Ue804+ Aba tH ie dieAelh to isolate Hf fom aulfine gal / 6, what is the Perpost of “thie reaction 29 | et ,_soilibe : appeals < following Tunprotawt taxkor | alkane 8 Alle! halicle Avene 6% Alert o Durie he ytresic of ee Co Or alley tolls, alkene vewal" os Neopian, cone. 80 Now, this allueme Tepounity tom be yewrowacl log passing Ha preduel wdetane throgh Cone. Hy oqi ye Mitte of aluene and alltane can he Stpavaled by passig Ane witlure thvegh conc. 2504, where Alken fs ausorbed aud | alkame i ceparatcd, | Mow the colution of ales! ydrogen sulfate im eone. bhstq joe dealing Gives alteve —loack. jr Tre allyl hydrogen quole in tl64 on dilution wilh aber fplowel by Weal viele Gn alestel “ yd —hof, 4 Of0gH on ein 43° # Overa yeaetion ccheme: 2 | ESS 1 ot! | oF tho yk ~oH +k — xX | Alkeve 4 Arcovel selectivity of Hydyatfow ' + Symmdrical — oluene wir vol exibbit neqiocere tiv ; so seleebivig: Unsyerwhicol Alkane + ghome —veziosee ctv He ® re) ure < tess cdable tae 1 wc St ot were calle a Use. ocbd! the i ~ 4,0 — Nye eT ONG - tre ' iz, Hae Gee for unsywunttricnd alikenes, ‘reaetion howd “eopotaleciy os the Yeaetion proces through Carbo Cation internedialy. d, olaviowsty venthion IU Jovocacd Hovough, wore Calole Aranciton glate oY — aarrexpondiv) wore latele eavloo cation ne. viv oo TS whlch vequived lower Ea, CH follow wovkountkoff¢ rte) uaidieally | Tablem! Gigs “he ftleahg resell wechoultllenly : Hain fawn @ Nps : aan tt Vey J Aa sod Helo %y 9 no £e Le eu. 4 a ay coy @ L gies Gwe do % Cation | (05 weoeterad say B KC ing fe VE, hens 6 wanted, 29 | So, by this wamnngement Wore Sfobie “e ring forwration occurs. ; | ° ve “> = Z i ad be ro “ue | Substrate Atkene or Glefin Resjewt ! O tg OAc), Uereuric acetate f ® THR, Ho Holy oH . Reaction allen oo emevcuratton . a Nechantin | Bt ha Intermediate ae | Ton, rmedile eleronele te Kngow \ os OS wereurivilt| | 2y60 4 7 THO im oo Sh ee | ‘Se, cantly | DB ecunkba, tse Ony merevrotionse a he 4 J Xign HBE HRIS, . +o Ne Q ° i Nt / me . (an g® he om ee i | * “ BH |o | \a a oer), CEB cn THe #20 : Ce tan OL, + Symmeneat arene o8 ho ltclechivit 4 a y Sh Pepiecclectivi : Pegioselectivity fs obcened tn uncgramelvieal ptkene Go J Sib. CF istovted_Iaderwcnke(?) R THE Wz0 >sodi he Bord pobrisation occurs a fromm Coos bond so this v3] bord length Tneveases Cowpore fo Cprim—Hy bord. ; gohe Ky ttt Ho ROH 7. pisimeted intermedlofe crial partial Ove clan rvac} Sulostitubed ennbon cide Ga % In tee exavgle), Which again et atabitlty boy the +f offed of 2 YUP. Now dis center becomes more clachoptitie nek OMY nucteaphiee 4p aiteck fais Carbon center, > [Regiocolechiviy, explanation ] Over Now from thls above weehanism id is clear fuol internal oleohol js obtained during on /py from ungymmelical alleen Conf» Hydetion aSS ey 7 DM 2 Sahat Ee ilferene Leluson _hydraiion, avd OO Migr tnlrwetiake, co ion : Ais Th OUD, there ie no free ee came make me question ovices —vaganding | the | room eval ole Fr We qat Unteanranged ater f; Abie methodology wo Ke. To abn, ME weft i Wee Hee wy — one | i) | bre [seme an | i | The reactivity of Aifferet oltencs Mex, | Aowords werenration i¢ comtvota) ly Ao | the combination of cleric and elehouc, 2 $8 | factors, : rong 2 | Une Aleobal. [* BW Terminal dauble bod fc more reodlive Ha | inferral double bord . Greve) Disubeituted terminal alkenes, however one wore veostive ton | wowo- ankectituted cose, af would be expedlad for elects pbc | attack. (Electrewic) SB What ic the wajor pelt ovtaimed th the Bowing veseHan— & DACA THE Ho @ wom ey 2 Ai! Hg Oe). watt iia Chemocalectively chooce Ces sterically cxoredad) co) A ib, en eu al Natty f54, . He, omy nucleophile , Ho reqiocelectively otteck gq at the dowivel athene pore to futernal double Lord ‘Now, wore ele bron ile, ceenndany Conbow (0),95n__ Syrereuraton~ Demerumtion Rection , Ihe solved sal if wixbuc of “IMP oxdal freed Prevonlotin Feee Hg(one), “Witt oat weak As Reefer bond ie velatvely wank so tiny enslly broken , \ Here | &e or ch veheove as MO y Bro gy tO ant? Now When the x -clechong of the alkenes approach towards fr, 07 Ce thew one of the Valogan adonn accept the elocvon owl yeleate the Shoal elector fo the Othey baloytn afmWe can vepween! the mechanim oS fllowe — if 186 ® : " Br. ode owt | ea — Ke 4 fr sates Prevent | ‘edble ~ Qe Why cycle bromoriey ilerweckiale 9 “Wee ‘By! ye BE sae | Chat, Les stable wy Ae o | dip tu, + BE oy vicine di ride wm Tnlevnndicke $s Fornnedd ingttad. of carbodeaHer wore “olole ‘ Oth cotecien Werwedile Quel chanped trowensne — covtbon atom is soxted wheaneas Pr bromonium foe Loa (except hydragen) all other odome axe have fully -fied | tb eed » 80 browenium Sntervadiate fo. yore Stable compare | Corvocotion tnhermatiahe YW carbocation fotermedlale, @valy charged carbon center if close # Clectronieally rich Ryowine all, 60 obviously Rrowine Cp will obfack the elechon deficient adjacent cavbon ewer, Stem com you prove chemically that frowine addition reockion Proceed wot tnvoutt cartocation intermediate 7 , Ho Be ween Bg A On tr, flere thie canon deeletsn Hance, the veacHon doesnot does vot Proceed though Codescation Trlermsdtate 8 Holeewlon orbital trternettow Fevolved tn the five Step ef ine pilowig veoeHow Tp u 1 rae x 4, Br ——t —_, Yeamouge a vicinal derowide yee ween Nee AE Fea gy | OM Wowie ig Wily 35 ccc The molecular ertstah fweraction Thvolved fy fr, adultion Yeaetion is oS follows = + Mkens ov Olefin act 5 a nucleophile so i HOM ® weg BO interaction + On the other howd, By Oct a8 an edeetophile, 40, iE 70" auo” Th used er Telemttibn.Re cyan Whenever our ferget ic to propre 152° dina cen iL Hl 1g. CH, Cy» hen obviout ly cohent should be von-nuclenplUle eng, Orch Clg +s Inert solvant a Hb colker . how Hy, WOH produck of 4n9 Ws used og the solvent, the vraction wit te a vicinal baleny din. Ch =a, +e, tho, fs fe ee Teal : Trenehydrin — Ubaleconsfounah % be T ra Higfdy stedeos Grbalive Gia Crowded cxluvove NH cath wo by bn » @ Stereokewical proof + The nm te addition of waleie acid Odd whereas Here, the of me wotecinte Weehenicn woe of browne to wot -fud 4p give Aowle iernrdicke cuggetiea. yf Roberts 4nd Gvrleoll Fcomeric uncalurated acid. Prowinatin, Vocernie. sediditre Miocene *teciri, mreco-icomer Wot oblainod, trom fumorn odd. sleveschewical dludy trdieate the anfi- odditior- i Neso-tonpound — ¢ | my oH | & a | | @Pecewie wivtove ” sCOgH 2 i Mn oS * Spm a LBS et | aa not iS . . @ a eo, i pe ue Or wtcS i TE) a | Srectnte ee pat | sbi Stertochesishr) | Gs suneaneneuigamtaeer ns CC) Araus . @u trons a tl ingelive Bromine ; : : reduel — yshe: adcition sith tvane-1- phenyl propane ylelds Tor’ aati addition, c Yeas uilth travs-2-butene yields 1007 onli-addition product usual bromine additlon reaeHon is 100% anti - addition. where brovwide attack axaally oppocite face of bromoniunn intermediate. Rud fr’ case of drane.e1! phenyt propane che frtevmadiate fs expackel to be an ‘equiiivrlum mixtine of eydle bromenium fon and a classical Canbocation intermediate Coxe benzy Ue) Here fo come extent classical carbocation is ako forma? becouse of the — premnce of alectron donating benzene sing which Cam clatbni2s the cantoocohlon intermediate tinrgh corguqation . a a ee ty yew Pg Solved 1\ yy Ph Phs Ree eg sd be Sgn -odie aut odaitlon protuet Product . Eeperimentaty ih Js observed that anfi-additon produel Fe Foy and etd 307. Is syn -addition — product: In case of tranc-2- butene the possible classical CantoocatHon has no cuch resonance stability of Wyher order. $0 bere the Inormediate is a cycle bromonum fon which fs attocked boy . bromide fon fin tootk cide and tence we got onby anfi-addition | pro duet. "Pe fer, 4 Hs te 4 | bya cay WEN 7B Ms " br : 100%. auti- addition producefe 2 ene i Tel wt canilder The addition ef bromive eve we gel both At-.and 14- addition produc | fy | 7 &, < | a~4 a — NA at 7 4 - 12 addition. | 44 «audition pal dt ie ive | Dice H woe halieved that the vinetion ‘followed eycle | wembered browonium intermediate | | ~~ _, Vm a fr a ° I Pin oe wee 4 . ft 8 ‘tobe be Bet according 1 UOT the atone wechawitin ie rel Mi Ting thk reaction se hove 40 concider Homo for diene Br Rip uoleeute | addition 4o diene tc possible when two adjacent carlon atom mY 1 1, OGG) com internet with Frome woleeute. | | | / | i. | | Mow. the came oT cleardy explain that Or | i-elochehration woke nen Bigs | This class af! yeoeilom ate carviad out on uncotwaled acid Here the nucleophile fc covborytate and the produet {¢ lactone “Tle type of daemime-—yeaeton nonin as Teron lectonieation or iodotoehmization, © Heve , flermoleentan attoek on te tlle fon ea nk Conpcle .oitn He « oa Bra at aoa rey, my Pe | «TE Any firwatin ceaetion Js inettally Conhelled el Cowepl Fa come pected cose) . 2 Ay a 5 to 8 ——— +; bs trowontum fon bY tbo rvoleentar eve 7 Lop eo 7 a % Problem + ao The major product formed fa the yencton giver ballod is - pA Aa! 8 ‘ace, a a/a wi oo Nae, y Cr fa a a write, 94, 8 p> Sieale Gabon h hay a ne non boot — aleove olde ic Sey Sra: 4 fe Tie Cantau, | MOVE accesiite os A bridge | Wee de Howe ov cing Goren loridge . Ge» Toconiuwe Tnbernecliae IU for from above tres,yt Peri rl boninain een: | ‘, T, corcenbration| genic potion Low Br, Cares erst th pr - oy oy Renaylic browination | yee coke tat | he : obcemed eee | Fat Appurion Sa | 2AcTON # Ros | wy cy 4eee > TT ther oy [ ie a 3 Hr + a Substitution eh oe Hee Tong dae Aetaitow product Cisewved Predued 46 = kw (rT fer] EG tect] . a = om. Lor, |e) --@ ou we are ing “do” wine oe hole a oleta: | ot inter medtate . as oe ] toad, OO] fee] * toe OL, | * [Cha] SE fold -. 9 | Dive ogung by “= @ 40c) , | # . ee acter) te ts (080 Je) o , aProne Hoe aloo encou Neo is @ chscr—en, $eh, The etbod Reblew: Ge numboer of Bilosirg veoetons — oy pig chemical Uivello ch Wis uy Sabiditetion reaction (Aliytic browivakin) we dawe fe rreinlain Tae lod bowinw Comenhotion — tevdition dean tok . be the — beck Choice for that perpowse Mechanlm for ountic Rrowivallan + stnitiotbn + ey, ee, ww, OREO Re Eg ya teat by ee by Arobis Frobdlyronitrile Caran x 40k __, I 4 be N Gulthitubion Reactor get pase =H Ge u of cpnitecleing oly! chioride is called the “Goeld . Process, the produc fnclucliyy Core ko rial found kowere Formed nthe dpe, M7 O85 6 © : _ OT @4 & 1 : As! = Syeludivg Es Gece te wvare ® be * Bowen, ® oy ai Aeracicrnare @)“The Wop pred fama iv the ie - Attossiny reaction te nectar), = “WY Clg . Pel Xue: wee 82g 4“ c ug oy oo om NRE + HRY, + Gaecabide s Trons +1.2-diproroacelephenow o f Electrophie Aaditow of bye boides to ovleenss a aca ay PA preparation Pension Hydryew alide haw allawed to reared wsitty alkene iw presenee of — kou-pelan elvent Oy Cele Loh de. then there orcurt ov ibe Yl of ate tale ® ge t, woe + oe ce ue hie Bey halide CHy Oe eh oy ~a0% rn + HR “tHe? Gi tig th — OH Uh Uy | i ue “he of fydmjen Louider weflech Jair ala fe ovate HF ur te the OW acl of the tydragon ball ad UE weakest $0 tie reoctivity order of UK doward ofan if Mle ~ a8 Plows UP CHI < Hee Cue ae Aedeitg in creases AS Wel OS Yeneivity alto ine se * General Mecuaviche Scheuw + ‘ mh ae xg wax Bop Sle, +x 1 AN ar *4 uw Bulow. Carlee tation (tau) a) eteenaae Now. in ond Shep nucleophile add fo the gen Alnasveu—— 4 i: 4 4 10 we Aly) bolide © Lepomlecivity of iydregen balide addblion « ar 7 Narkoanikovs Rade & Pindple a hydvoyew halide om add fo om tun Cymmetieal gikene fe Bitar of tuo diveeHonc, In practice, oddion fk hey weyincelective af ty be considered seqio specific. PONTO PWT 4 RU ga dtu!” Belch, tod Ree act, 4 yx a ae prorat i Yathor thon ec —olp x4 ak Recowde thx ——, Rac—cHR vather tar Pro CHR, Vk nod xa Ix From tne above experimenlol ebgenvaifon Warkowoniiav proposal ov Awple tlolewent uadr os Morkoduilove Rule * Whew ow unsymmahically uectiverd alkenes scea.et ubithy a hydrogen halide, the ydhrogen “adda 0 tat Carlow Which thas the Greadey number of hydrogen dom qubetivent, aud the foun adds 40 that Carbow which wat farer numker of yydrogon © HecRosstic Kavis. for Markowrshov's Rule « 2 i Stay [ate ae eis ® BacimcHe | | (0 @ | 7 4 Gass Sabie) | ls . | p Reco ea | fine Lk a Aimer predict | CHajpr a) mor) | Eedudve preclvel1 o J suis qundtion product Brnatiow (wajot) Axtell oe fe Gwlev mediate lability. tity ineveoce of carbocatfony stole! ty ee (the pak formation rake os wel of eAaipy praduct als Cane owe | tds Gide. : rnterachion’ Involved j Rete ne Fronticn oebital Teewanses Rance jinte rach i ee | fe tke formathw of the carboratlow Yudermediate fur renetiow . of fco-ludylene with Het — Ba of cleft ora 6 of tel @ mw w+ 7 8 & of Hel @n.. =" ww, Atel, Ons. “6 of wel, EE Baring Her addiHiow 4a {so-bidylenus olefiw #6 condiderad a due deehow rich epeeies Te Nuclesphile dherat © cowas for at. “thus , Homo of alefin ound LUMO of Hel fc condidered br she forwotton of woleewtar orbeitah ingfaod of dhe yeverce. Covoinotows as tic eatbatatiom combinatow ment oy {pwel” Homo ~ LOMO energy gap. Srbital diogram ef renetlow of iso bubytne weit Hel are aS hon boallo® — ‘ Hp ean he uePr te following, demant Varkownikev, odditlow, reathinn , Abs produce A ond & ove — a HBr, gg p, OS Hemmer | eb iacionmmre @ Crandiners, @ Hite ay : apbisonss a he y / aaa : eo - Gxrtocation Ini. Ar & Te Sp_ bybridi ved i one. ee fer “TT tw ota elitr @ ® Gas to vive toe T___ 5 Pritiwel¢ > Oladlenes eer @ Stereochewie of HX addition + © The stereocRemichy of the addition veotlion of Hel or HBr ty the unconjugated alkane (eq. 2- Sineligl eycloherene,, eydohasene , Cyclo pentane) r-twtene ete.) fr von-polar medium ie franc + The reachon gnbibils third order kinetics Pate = [atiene]' Cues]? Oe he #8 compugated, —acjeci wit am ary! group syn- addition, via jon paly weehonin te volly observed : + Tn this cose yeaetion follow 24 order Kinehies, Ay 4 Ton poir Bote ok (Atkene] Hx] Gy @ HM odkene Poue the feakines fo give yeannanjement then there Obviously occurs veanovged pty we By BNE Sinan, Me! © a ' Ml Hy bac’® Wor tertve Stile yiblls came pyrtuete {hal ave explained toy the frat of non ~elassient carbocation, dayl! Shgle at ey aid Che tA ce i [os ef 1: : ~ 1 he che 2 cet W) Aueleophitie golvewk dead fo ay wixlure of produc. Ph Bs tectnen ir ft Hone? pe A Be = eH mcrig + @ Cocewic wabrtuve) @ SEEKS In Mer elton of peene , 2} te urd that the alkenes “ Undergo auti-addition ello vale tam: vale =k Glkene](uer]'s Wile the alkene frat underypes cyn addition, follow, rate Lads rote © k [alkene] Guay]. Explain. Doble ¢ ; Ae ongauie compound. Db (Gee) te ptitie fo Reeyerc feat, bul Med to cocliunn welel. On tveaf ment with cone, Her, P gives CHycrct oud CHeCHO. “he meltue tg 9 tos PF Noe a here ®NonNe Kos Positive to payer's feud that ueore un caburatid , Bret to codium neal, Thus Oph. @ fs not On treatment Vesull, Lelt ste pectible. witty Hel, tno moduelt cieayel and cilpexo As ie, Ag bs ABA Gwe od — exeese as it Tewolw l 4 ee Wah conceuahinea J butane and 2 bulene whichis ave vioclive fowmrde 1 rutaition> ——— SauGn Tee Both reactant veel with HI to yi j 2 } jo yield the came produc , geTototatone via the same inkevmtilae, 0) steondany yt cortecin. : 7 4 sere oe oe fnlecrnedi okt 2 bulone of the two slaving getwtene je more stable ttow, snot the endothermic. alkene, dep of he woeton fee, Alco note 2 butene due 40 hyper conjugal! rato- cletosnini me! et yeadtions © as ‘olfoue~ forwalion of — corbscation ic profile ayo of lhere tuo Thus the energy vob vaun t ie clartot Je butene From she oeteBon anegy ann HE OTe Wore reottive tate (lower fay) compare rte cere chiffevenk but torands 42. odditfon. Obviously breve Go eneryy of the = eae ee ee vg the some TE avd a coud with ester H? addition. Hemee, unctalole reastand proces Compare fo lable veoetant. Potton: The folloeuig tWo olkene oxhizit appocite veabatlectinity i Witty Hie fee awd aa Pyplain, Algo prectict Set wives of dhe Ho fra oll wreak ok ov faster votes . i ead the hen freoded. walthy WRr would — proce pmrrebical lant im ciple. trkerediale of $KOk pathway eu the bh mor dable of ‘ i ml eneryy- associated — wity lower acti vadlo nexyy pe’ TER bak detlised toy dorg I effeck of Cy croup i | Fee’ 7~O, 1 but rerotive! a ee | Le j ya Ao Ryome chs No Cavincation stabilced by tse Pe Her KU atone ave declabiliseel CH,8. ge TP etfect of css qreep CHa % carhocation , Resenance ¢tabllisaton Pe ag nitty ae! | . on infer otions ens on, eu Here, 2"4 compound Le. ‘eval elher reoek of Facher rote than, trifluromelnyt Guodtituted alkene at the | Corresponding — cavbocatiow fr mere clalele and hence fovuned | foutav. TB Pevoiiae feet * ee ; “The odditlow of Ry ds deb 2- wromoloufone . (Marrounikoft ade tien) go. te MC GH cH cH 4H RY on cab “Ally 1 bales ot badine bude Fed bot if you wout to gy winetite I-bromabnlons fem ter fous hho ond ‘reoqend Rr 2 Now, we, largely Anti Vosrkonrikotf addition produet , ae ee THis target procuct formation “ean be achived We indtdues bromine of an electmphle than thal bromine Wit. connect to the terminal carbon fo. result tte tonget | product: « Fromine — dechropivie cow be dered H we em uso bromine radical, | VOR brewing radital generator Prom Hey | jc possitele by Feroclucing o& Tosital lnutlator je tee peretids | * Dnitiation ¢, | | | by . Be apg. 4 Radical is +2 cowpea Ht ochle. pa! le > pou + Rr © Propogetion Step nen, ct clay D ayaa galery be ——> cura Suey, wor Altoxy yodical Wytly reactive tecauce + cake an electron @ : ' @ Oe tM —> cyclone, sar 4 bromwolovdaue wm Why fe peroxide effel oleerved fr the odditin of HR put not fr Ane oddillem of wee Wel ov W492 “thir quediion com be onewened by cgleutobing Ne go fepagetion sleps Tr the vadieal chain reaction (Using Ue bond aisoctation ontrgy )Mo4 dh =c a = igen ae AH MGW Gage = H1d Hoole Keyu) Gaia, FH yt ma ay gel! guts tat -lor = Years (| aca a Peeeeenesanone ae fe we Bech cH, gy? = 62-69 © 6 rool : ; 10 Br-ch, CH, tH Ry > by -cH, - . . Pench ce 40K = 99-19) = ~14 Fem ' era he ee epee 5) a * 247 Keil an" = 62-562 47 Kolar) 20 Kealv! (Geo) Toon tt, 4 4 Z ‘ et Pm EE ues na aoy = From the aleve 4H caleulotion, it i clear dal only boll propagation ctepe ave exothermic in HRr addition in presonee of H,0z “Thus thic propagation sieps_ can compele with tte termiralion, Gep, whereas other HU, HI addition cord compote witty tex mivabion. dap (are erly exetuerrmc) “Thole aby Mitr cow ovr shi>, peroxide effet B Fermotion of Gsgovoberanes eae Hiydvobaratlon. Peaelon ul md os tthe addition of borane (Hz) across clube tword ey | | te finic compound dhe acton of diloorone (ite) om an at d Sats ve noun o¢ badrofooretion xeoetion rm alley borane, exgoncterene | olefin N\ ‘iar Cotati 10) 3 Rag fasta | Solent ‘ey. THE oF digtyme. * The reaction i Sterenspecife cic adchition. © Reastion appert fo be antt- Markonitkol wood % 4 un red tromsitow + Renetion occurs tm ay deel step “four mewJoen sin # se — | ae | Cis produek | en ‘wgig | *) fo. | Hele ee | yn Flechron deficieul | Ly omut portal Thus A+ elechons gf c-€ double bond abtack tty wore Aleck pocitive Rerom alow, While a hydrogen atown Of the hevane attaches Hee Jo the wele@tropotitive Canton towDuring hy cobovation alkene acte of a nuciesphile Ob well ee: ew) eleatrophile. In ts reacHow Ain alken,, engoges tn two fateraehions. “Thie venetion i invtioled ty the mweleophic attack of x -orbital of alkene, the Hom, to the LwMo of boven compound, fe te Orly p orbital of born, the weaction oe of the 6 - bending M0 orbital of alkene, LUMO. ith the Pu shen ends with a OP, the Houo, #0 Ue Atm of H-B bord, Cone —> Crone on = These fyontier orbital pictures yeinforte the bercertion that fhe C-R and the 6-H bonds are formed | Tndepe ndanty, i ec ic : ; Busing yd woretion of alkene’ do vol greed up Ihe ventHom as walt os Wey do when? alkene ane Maced ey other ekehophiler . : | 2 Orgmoborane brejenise, 5 = Aesth tahoe dene JorB AP the admare te Sy Te 2ither i i 7 dhe GN ut ems ge co rane sR a one oa ee.B.| me wi = Gubctitebed gl : Te ene Cmnove, hrindewe ¥ Bislavege bevane « wore hindewed) give ctialuyl haiane or 28-1 Siaxe—H | 4 2 axk—u | 5-5 owt borane atl | Seordary The reogen cho ‘ roger ld be used Tmmedintely after preparation « Bisfam 5 "emy\ borane provides fox Chenon,ver}io- and stereoselective lydrovexation. ® ten m , : " Even. ..imove”: cubttiuded’” altene » ine tehnswladtiluted tuene qusuth Wono~alkyt borane =i | = REM, ate 4. : Le oe enn i | “thesyle brome thy = 0, » AD ‘ al 4 e yeast shough thle mone luytatad borne Te cromded , it wll Pydrotanabe | We additional sixenec provided they cre no4 foo. Wnderad B 4-@raviesto [2-24]. nonane (3-B2N) ¢ fydreboralion of J.S- cydaocadrene ; Can be prepared by tite one equivalent of Rly. | a aon © oy) | @ Reglosclectivity of Uydroberation _Pesetlon + OREN Gx Tepatent eile oot Mycobendtie. tension fo tg cmp i 1oScleeh}- Vig observed with uncyrmmetol alkenes Lincs ore he faedors oy ponomvetars whiely oan delermine tho reginclecivity af the addition vreoction 7 ion effeet, romnanee. ard steric Tncluetive effeel, uypeveorjupati effect of the alkene. ond the nakere of (steric) Inydtolosratlng ofpial, 4 an tot dn = Ci, + H-RM, —> Gt 7 tie HORM, 6 * be He geo on =o tH, ae ao a my Le—i, Beh cH 8 eledtren gyal | oo enmity | \ Wy | Ee | tS \ the Mae, te Fac, ees eens — | bites ne NY Hy pecconjeqatin Revevce eypereenjug ations Bw tie venetiow, vacant prorbital of boron i borne, To Frvolved with He A- orbital of te alkene. this finferciction Jeods 40 partial presse nenalive chorge ow Carbon. Transfey of bydrogen uth ik © laonded —eleetrow paix from bovow to the carbon Inal ean bess accomedale tht partial positive charye vie the four cenoved, TS, Greneratly, boow attacks fosition of Wiyhest election deity md lowest stemic congugattow A Problem Tt Addl ots ity te | @ Audi - bon koonikey a leze fe Sym - addition @ Andi ~ morkeuiyey — qudi - addition ie Moriedwikoy — Gy ~ addition i ® Monlerwiker - ei Addition Pht: Chewsical renetion fr volvemed Tv the vealon cam lee | iUuchoted as 4 | eeen eo, Me 2 -a—on, | en Co . Les ws. 6H oud TH unl attacks from tre come Ade ee Syn vee on Beetror cloficlant boron atkoch to Hat — Cankon, whith Corda. qreotor yo, of bs edo te Mankownikov ae meee ee &.- opt © tc Corre aerp _chewosslety oR , 4 Gonpies: THE rales of fydrohoration of aluanes wih dialkyl bovanes vary over a wide range. Thus it to poisitlg 40 selectively reas! ove double bord. , in presance of other tn diene sypiarn. Relate votes of tydroboralion willy dialkyl boranes art 8 followe — FOR 'Y R-cr coy, > poy cene > Re gem -di wono te cH =H, REHALY Open oe \O gexacnR) Re HHR mono ged aia 4 a ono ie There at Hale OF =a Ma 000 CH= AI cl - cH, 3 a yo 99 9s 6 wivor. — di 7 ‘ sia,B4 fy “) ny RSia, po te stots CH Gan) 850, SS i i que di Stereache | Stereo selectivity of tydrobondion + The tur centered Ts for hydohoration of alkene incpliae tat additon Of B-H ord fo a double bond proceads Pa a syn-Meahner ov Git fashion. hy fale Whey, op a" : THE Diatiyt borane. _ Such as oF pinene, vesulls inthe "es bindered fre of the weleeule = dehoration of a bieyelie alkene addition of 6-H trom the % give (Sec), 2-H mye. (§pe Mel Ry uv 8H, Bager group (ere prjcded ale» troll fre from Ral come ; vt ane von ion aol Wy tog caroan Whereas Ss. 40 ovoid ctevit sis te ne sterenseleetivity on Wow, the veqloalechivihy explains OL Tem lz attack ah the wore wivdered Tl, unit gurach foie, lest bindared ag Combe” Sit Ge Contam re: Henee, Hyroboration tnvolvee t + Rayfocalectivity, oddition of @-H + Gc -oddition of @-H + pddition of R-H from lae-hindosd face (ctereacdestivty) + ChemoselecHvity olko obeervid fm case of diene OF Ariene eke: @ Rendions of _ Orpproberones From Mena $ ‘he aiffevenk cyrthetie ule of Grgomobmmne are OS follows = OuidoBion of Orgonolvormne to -Mesbele RB csc, —P—9 Rot, “tly ot Lo foun - { The? CW -A} eho Jay 8-0 Uydroboration folfowed ley in ky oxtdafion by alkaline Hho, providec the aut swarkernikey Wydration of double lord. 23 ++ 2a, trast ——> VRSU 4 a RlySo con # eon oH OG), + 2eeH Seite AF td 2M bed tector ily sendile ‘salendia, af configuration aliowing the eyntiecic of aleobek of predictable ereachorihy (arf ae 1 t0- F0% : 2 1 icici The migrating group rulaivs ik sheveacherssty ud HF a aE Troupe ore altached to boron, he order af case of iqval © wally ~ ee ee Prva sendy Y Herton. J 1 eterna seg es oe bydrobovotlon reawtion ic nol accompanied Gate 3 é Vote. covvotatow ane vol formed © ay trkerwaal cee Con oo used —waittrouk conpplitim thal few accowsbonied other addition craton, ies Opt ats Oxymereuration ~ deweyeuvotlow Cou -Du) and, uydroboration -ovidelen. ore wmpet—6 fowblementary 4 cade obber, [R-ae 64, JOR ag, Ta me TE PBT selon wang “CH Been o, : i i (Pvtecvat Aleoal)| & he 4 femal cove i Pilg Mc Haw tor wi Kev | sti hoy, wd ——— Hon | Texwinel Alechel \ Andie wo bonus KOv | ly dati | say veadlon Caner — [Rete — paediy ne groduck fy tee Howley“ a ara, Ah, 2 © | THe OH eu ‘8 , | @ OM, 0 Cha, O Cote s Parens | fa i . oN en tig ESS Bh, as Bs Bag ’ THROW Ms: 4 + Ouly used couceph ic Cayiaclediiy. Hthe 20s © We. cu ft 2 | + Whe P(x) is dread wit POC thew opl. @) will rest. | Wiikey of the fellow slefin wail Alte vatemle alcelel oye Faction using) [= 1 : after Wydvloevad low " iw THE followed by oridadiow — whtw hoy ©) 9m 6 Oe Rocewte veal — ah cola) odcohals beermes cbiral , aud unsymmelieal — olen. Wi vest Dew product eWrot leo! wl fore ln ; auc ere aly unegmelicod atuene Te ophow ©. | Go thie olen wi risk Yate gjtotal Fave o sot | — ates ow 6 : i . oe 2 —tee, iv aleve “OM ow { @ Rasemie main,eee + epltw ' ‘i Wo prediel attained te the Fatlsiny Hows favecatlay Poy MEL Mig how nay Ne ance vi i fay) Crinwatn, i yh) + Robles — Cre plete by Ganainy fo © Fite ee? ; 7] tee LL ' wow ] PO Ms Thee 1X Mono of cyclspentadtene G4 2 Maaladicue) ered wit Lumo he Vato “p'-ovuital of '@' atom te Rly, Pichew dantity ab g aud Cy of cydopenladieue are Wighey go yeqioseleedivdy bevow Commect to {he terminal Carton, “thal hy the above produel.. ® Corer of Orqeve boxave do Pelewary _cwtee . devanims 29/8 vay bye oo Ki, on better Nieorg I apa) One rep Chiovanine — or Togstetaded hydvory ty Antwe con sive the ax peeled produeh. ot (a M0 wets) aS Pe-{une) 4 R, Bloyt TENN etre Benne), Priors uci| \® Conversion e TE ef _Orqaroborme ta alkanes wh — (Protas | faxay Alkene ————» Alkawre i = 7 hic de wow: calalifie meted of vedwctons EF Oak SESS alten 7 wh wih aces atid be aes ar tialkyl borane weaked llkeunt | ste cen), @ UAC 9g payer, Mectnowitun | ae, Ae e Ce Hy ~ 07 es taem nee RE nonce Son Om Lea; COM ® ace Q Ep 9 ae W 4 BY _— F Gy coo <¥ ¥, u c-8-oe, +(-[ Alkane Geo), @ 4 ZRH THE D. 1B D oj aie” Chewe cetectvty Allowed wy ae Reyqer borane” prefer lee eroded can 6 cals Ua §. How cam we Comy out the meduetion al ture tnlered presemee ef tess Uderad olefin ef byqaueberere empeiwel! One of the wot vercalile application jig tyeitel wc oF ui alter bovame fs tthe renetion of canbow wowovide with __coUleh th, ke ont Tee ow ~~ 28 Ahaligl Rey me flocae ian weehou A A owsleenlor aes stops Twowe a cevies of Inver ctuccesvive we Meentnls witty tne wiqration: of aluyt qronts 45 sed to drop the. final é orewle aid derivative \ ot he He emmy cys Ce Sg weg By, Ry Ais melted we caw troncky av wore selele fnterval alkene, to unttable lemival alkene » Aiodly? earetro| © To meritatin of omanoboomes +, i Wher aw alleyllovane i ated at e-Sc0% Organoborane. Ore frowned. fo a winture of product I whieh tne wnajor comeporerd or product in the orgovoborave iv Whlel Lover alow okkack at Ake terminal convon The —precees 16 Cotalyper fy the addition of dieymmne, and here a sequertal atminadlon. and addition tepe Secure thus ley heativg condition internal woron otown somerized fo the termiral arbon oben. AN 54. om ob ; Bac 4p Rate Fes rite, Ac Oly yt feo Hy, Ay once ae : * Bly do cum borane undergo isomertzation 2 ne Avs. Akg boone Undergo teorrerizatin because of the vovetsible Valure of vydroboodion a4 bgher tembevature avd obvisusly boron bas the tendency to athoch at the fevmval cartoon of the alkane to ovoid ctevfe crowding.+ Why aye Ahese —Teomericallon, deli inv gynlbedic 7 Sete Ry thie welled we con synthesize ay tecc eteeit ne rom a, worn able oluent. Wiiely fe aw usual conver’ + How —weluld you covivert_ 9 - Hexene fo 1-Wexeve 2 Oh See for ails conversion ne weed to ello nese three Seps : fe jeenee * | GD Chen athe th abl lle ROR ME \ dvi lovee | i s% obtain, | © ew the orgareboraws te heatel o cca See b te | Ol oligtborane fv ae toro few atrachsck | tewwival — conbow. \ ; olkous- | @ tne Teowariaed - allyliavane te Weatod ity ates ie | kicks Das ov baling pair Wifey thaw M0 “4 | alkene te dililel off aang nD Y Far a AL 16tte qenperohine there oceans sequential et, Fotowsed ty addition, venton, hers a wore stakde — orygpind board | weaut Chrvae ov wovertble —rroton achat, Jor, ae ee) SS tama sera Oat ‘1 ee fey 1 fey aye, PMO ~ Ula tO cy fates hs 1 tach ac mi The teomerleclim fomenized abeytlinone te thew tealad alle Wig olin alkene 0g. A deen. Aiceodioted trlo A-hetene and a Compre), the allege torane asty fre Yerow Inydride gy fess voladile allyl borane und atlowe oo the rove vedi 10%, diGtation. Coe = 2 4 Pay He iets dsherene Pate ee ve) | = HG, oC), “Ts Hranctrwation Converls wore 4 4 ple Pokle athena fo ters stable aiken 7" EIS oukent,__, Caers volatile)Pe | “ne Firman Hered ttdc punjod at “Covtattewscayranie Farrvei zation pot pee 5 Nom eae ym ravey aul the lining cenuetant 7 4 gia oro Nog the A c?) Ase Henin backward 1 way tne auvdicspaled What Jo commy ond the venuncd —comenion te ove in weed of dhe losing inbervadiols a) 4S % Inerval => Allee =p Aly! laowide => Alkane trgavobarane cal; Ste se § "ow {a0 Sonate par. [Ane Ses o: “on Loreos | S Prem 2 tow cam yow camy oul fot - | coe BCs), cw co | ee Ae fate BA 8 SO Sie ee [so0%, icomertaatlon Onn [er] Distined pa Whe fotiauiay Crmversion 2 tig th La) ey Me r Aistivaliy ros, —~eae —_—__—.. ¥ B Orono Fenelon # x reattiow i ow organie veaelibw Ghany A ey Oronslys wean | broke by thy = tie uncohullll doubles ple or oxo bord © venek user use of ome qos. Revene of Me . oe ee ond My ox e | ° THe ow oyldatlow ew venetlow Sceuct ow uncolinotld ovganic cowpourd triple + “thks renetlow te caved ont fo focate the double ev trp cue bond —potitlon Te Uncaltwabed orpawlc com ~ Beneks to SBE, meer, HOP, mre-ce, 2 +05 her bu by Motorowele Glyeot 2% Jes | fe: a Beg, Syed so + o8cR, Ea. | AERO FO eRe CA, OO Ozowlele- ace “wt a “laa e 2a a a C-6 bovd Uclecddition fission sy) Yeadtiow: Wuelorendde B. f0 FT Mg E Oya Pe NK | eR 3 i iat Thies aoe ee (ausithasini] on Ozone Ts om eleetophile ao Ht use te low-Wirg Lomo tat Overiads — willy fe otto’: ef the OMe, “therefore tne ‘presence of EWcye ow the accu. Te vegponsote for deevemte tw tae wate of — reatHow 06 the tonto ‘ “HOMO “energy gap Trereases, Ow tre other band ty presence COG g tthe olefin, ineveases the Hono - LUMO energy GOP between alkene and OZone aud. lence veattow rate Fnewenees. ~ For eno, arene ines much biter thanay poeeeeeee | 7 - fa proklere Which of dhe oiiowiw] 160 olefne Te wae prow dna otonatysis Yeaetion avd ihy ? Me om us ae sod js ae Me ut A cues ! Atkene 5 : : hs @ is wore prone tonne azonelys'e veoction Cemmpare to alkane . @. curing orerntysle sion ef ollene and WMO of 0; ore used in owidation Compare Jo reverse —cormmbrration , Ineveoses Uber alkere ¢ormectic 40 Hono energy jevel, energi i | EWS Compound A) whercac the HOMO energy level decreases Hf alkene comneeled to Tu (compound @) Thus energy gor Crete tune) decrees Te comb A canngare 40 combs A, Thal ty compd@ Fe pune fowerds — aronatytic veaetlon | | | ad Me Me tel ty 6G C ® ® fus Now the quettbn fe on does she Halo “energy level | Meveaset - whim 2pm, are present 40 the olefinic Coxon? J To evplain thie we how da consider the following opproximalime — energy profile woleulan ~ orbital presentation, Os Lomo c 4 yt 4 * f . FG / Hono / i i —/ F-E06, oleore enevqy profile, ik ts cleay that a eregy Yop minimum wen alkent conden am ERR On the othey hand the. eneryy gap Freveses Bhen olkere & commect to eG. “that’s sy he above result Obtained « ae econ Atkone 25 Motoronide z> Oronide te 7 ‘ Pradvel vedi. amd i Ozonolysic reaction .Oronie Aly er ® © nert solverd OF Ug «Och ate Aer cowplelion of seoetion Sslveutr are auapovaleol. ition ee” oka Recowpasitiow Redudive Decowpastion Gridete _Doeompasitiny « Agr0 Yo, OY per Acids way double -vonded —covloons ive forvule. " 4 " tod’ at yn oe ae forwle aeld 2° double — bonded — corbont ive trey thon -forwie acetal. a ®. KE De a be odd. used Bx toe punpo Se - cantocriic eld P Soule banded — cankows ve: Kehna g a ol? OR a +o