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    Organic 1 Part 2

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    Organic 1 Part 2

    Copyright:

    © All Rights Reserved
    Download as PDF or read online from Scribd
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    26 views20 pages

    Kumar

    Uploaded by

    Comsip400
    Organic 1 Part 2

    Copyright:

    © All Rights Reserved
    Download as PDF or read online from Scribd
    Flag for inappropriate content
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    Ee) Enantiomer Ths Stexeo = Bomens —-gelated @ eaek othen a, “now superimpdsable — rwt2007 agen ak coiled — ShgeeeeASe (C Enanttomen aun sterectbomear eabeth possess object mt2207 Amage — xelakonship but do not —suypearopose ow each other) - Rrantiomns possess —tdentical —physteal poops namely ro:py bp , solubility , wefracttoe Andex ete. They only Affer ootth Bespect 60 the aotatkon, of Plane polawted Lyht- 24 one of the enanifomes 3 dextse rotatory , the other cwcll be Leavo zotetoay . Ravomie rntxcture 0 _Pacmic _modtiffcatlo A rméxtuse containcrg tuo enantiomen (dextoo leove) equal paopoarkoos cvcll have zero opttca) 2etattbn, as te etalon ue to “enantiomer coneels the. rotation clue to the other ond Suth mbatue 8 known as Facemic misture oF Tacertc modification. LEG wepresented as dh CPG). eg 4 butan-2-0/. The process —canveation a enantiomer to to a voeemte mixture & Lnoww ag Rocembation Retentton. — Retentton g —confyenatt> — the preseovadtbh totegrtly |G the spatfal aaoangement of bonds to an asymmetate — cantze using — chemécal Agackton 09 laanspanakin | Tne gensool, — duscig o Ataekion Teno bond to the stexeouotec & broken, the product anil have the same geneaal, Congigusation of gaoups aound the steseountee as that of — yeactant . fils - cts MRcacuz—oh 4nd Ss We oca—d 4 jigg i Cabs KS a Methyl bulano) “I-Chla20— 2-rrchng dee Mechanism of __ nucleephattr substitution Tearkinn. C Subetitedton — nucleaphdtec unimoleeulat) mechanism Tr this tye , the vale of the veackon clepends on the conantoad’on @ one of the veactank, (obeys jist orelss kimelics) the alkyl halle + eg- Cis, ¢-82 + of —yz its), C-olt + Ba Rage. =k [@usy¢-82) Sy’ veackon takes place > too ekeps. sh Formakon af — carbocatd. Slows Siép + 9 Cuvee ae at e ao =— Ek + cla Cl In this step, the polaxted c—B2 bond ncleageas cleavage to Egy ible Ried (93 op Piigeatony 2k ae A baomide bn. a This skp & glow — and zeveasible* ees the. rede f the renelfon depends ow the slow step, hee the ele g dhe cenctonw cleprends ow =the conceotoa— tin g the alky/ habte — ard not ow the conuntoakoy Fs nucleophile. Fuster qresker the Stability of the Cartocatton , greater ostll be cts ease of frrmatioo from alkyl. halide and ate of the, renetion, cstll be uty Spa Foamakoo 9 the — Substituteon product fost sep - The carbocation formed > dhe. fete slap Gnreeagoes — allack by —nucleephife to om che pooduct « F's a P Ge. Go + Na — tame a és © Te onde B veackotty g alkyl palicles @& rough — $, mechanitm & reeee () FP alkyl hatdles undeago SN seackon roy fast becauge g the stabicty 2 F corbocak’ons C#2 expert and, hypeconfugation efpect) © Patmary allytk — anc bengyte halties shou) greater acoukivity — theeugh Sy mechanitm — than patmonry Alkyt hvatstes. Thus 2 because allyu — and, bengybte corbocatrons ns. eG bly stable dus do emcee CH, = cn —2y, <—_y Sig —cu cn, Ga ten, te he a lz rela. ‘ s a ° Gesonane > oO <— a Se Go og dergytie corboendton) © Sy 7eackon o> geneaaly essed preke —polor Saiveais Ltke 420, alcohol, ackcaud ce 2 Iu te case of optically acttue alkyl alts, Sy reactions are accompanved by — Factombalton. The corbocakow formed me the 4st Sep d planar (sp hybotcu'ed) . Therefore the attack 4 Ha nucleophile Cis the second sie) takes pla = faom © bow Sieg wesullitg tas ménture @ pocdutts, one havily the some. ceméquraban Cas that of the ovighhal altyhalde) and the othr one haucig oppette — confdgusakion . For esearpl, —eptteally aaktve 2-boemobutane on hyduotyss — gives (4)-butan-2-01 CRacemic msetuse) Tes fe Blow $1 Bos ee ® —planot ‘eolas carbocation als “alas ( Sp telarhacha| ) (sp plans) aie fe cot aN on, Non =, cous Gus r “D @)- Badan-2-01 @- Butan-2-ol Se De eal LS vacamic. molxtuse Denclie votakny LT + lenvovotary- > Ea ent . Zu thés dype moechaniim, —reackbm take place one step and the ate of the seaciton depends on the coneantrakbo g both — alkyl halle and nucleephile eg. CH3d + of ——5 CH30H +ch” Rate = k usa) [om] . 4 4 ha eet $e ol ‘ 7 Tronsteton state Tv this -meehantem, the shoméing wt alkyl -holide causthg te coxbon— halide boog to bueak —cotile foaming a corboo —nucleephtle bond. Cbvansction tate) These two peomsses take place | 1~ f necleopile srteracts single Step and no soteamedldake the bond bekwan simaltaneousty th foamed . As the eaeHfon pooceeds nuclophcle and the caxbor atom — seats foaming the bedewveen the caabor atom and jenuiig gorp and the — bond seats breaking - Fitally the product is formed, GE Zn the bransiffen stale, the castor atom & simultaneously bonded to shcoming pucleephle and the outgoing leaving gooup cand such atauctures are unstable and cannot be igdated- BR cy because the carbow atom i the tansttfow state ao siroultanecusly bonded to five = atoms and therefore & unstable he oder g suactioily @ — yartous alkyl patties thoeugh Sf mechani¢m 3 Pytyd bi order B Teacttotly — cary be. explained t teams of Sstabllity of toansti~on state. Bulky alkyl gaeup present om oF rear the carbon coaryirg halogen make the teansétten state unstable due lo steate téinclrane and deerease the. seaettutty of — alkyt halacley ough Sf mechanism $ allyl hades are least reactive Secause bailey, groups hides the approaching nuckephiles. OF the Semple alkye hatuteles , methyl — paltdes rence wopelly 3 SF qeacton . Dn the case of cpttcally ackue —allkey/ habs, the preduee formed 0s w realt @ SF mechani hos Lhueated yuratloo as compared bo he Atactant - Ths A because the pucleeplale alack Ge corbow , Ow the Sick opposite to Ue one conere the halogn atom present - When, ©)-2-b20m00ckone 3 allecued & reat uxt ARO, Groctah-2-o1 B foamed ast _on grep eccupyiig the postt®» oppastte to chat boemidle Aad occupied Bo +O ele sv | Take plaw ® %ea3 Slaps G@ Slow sep 3 the sede chet Sep > dade = k [elkye atta) Cloesm clepend onde. cone 4 a] Anteomediade casbocakfon & foamed Ds the opttcaky, goomed mt setae O) codes teasitucly | aly Latches 252 rp | Gleak nucleophiles fouous ® alky. Hable & active, cot) be G xacamle Si meets poor solvests shy meeh a8 fey | cause fag ltBoWalia g \alkge Aokie and thus pactlitalin the foomotdorg, clependis entrabar g both Rode =k botegg balice) [na] Om Me cone. Pro ateomediak 5 soared Oia peoduct ese the predic owt o. conflpueabs epposk to tet & RX B observed C tueasion) 2-2 PLP 7 Slaong Bpoak'c less poles. solvents { | | | | | Lo Kléminat on Agackrons 2 when @ haloatkane containing Ary deepen 3 évented cx aleoholtt Kom, LF cancteazorr cle- yelo halegenvatebr, to foam alkene. Thés oackond called B-elSuimatton beause the hydoogen ators present at B- posto gti Aaloaleare dB oemeved Siege ® eee, Clg cH: + HB Th these 8 any possbiluty -foomaken Brame thaw one alkene — dlut the avaclabtity 4 mx thaw one B-H- atoms, the pacfeored alkene 5 that wWhaeth has greater Numies GB alkyl group attacked. to doubly bored = Carbon atone. Th 3 alec Sot ze ule - CHaeH—clh hla chs CHs —Clg—Ch2 —en—cik ale» Ca re CH3a—ha—cH=ch cs | The Ateautoty g hatoalkans focsaule etrmenakey Gib) folieras the cade S72>P (wy) The & beonnse erdiday alkye trolicis om cletysativelm — form mote substituted alleeres, cOhteh being more stable ave foamed at faster rake. Ow the ofter hand Paltyl halts poam least Substituted alkene. wstier being less stable cove soared at slower rate. The coe g venekotly of vartous alkyy hatter havdy game alkyl gooup 6 RIYRBSRY. Chemtnakon Verwas wbstédecttton « An alkyl pate cathy B—hydoeen atoms cohen trenlty wih a base can undeago Substdukbs ang C8 eleménakien. has there & a Competitor — Gakwenn subst futon and eléminaden. —whath doude 0 poedo— mieantip talon lepers cpon the. natoac oh fae alkyt Halide, strengity and sie @ base / nucleephile and the tensors conditions gach as — polartly of Solveot, Lemp ete, For example, —- - Pr alkyt pasides cunclego ebrl— matin, Slowest anq — Substitukon Cont) fastest - 0% the ofse hang 38° halide anreleage ebomcnakon, forstast and substttudon — slowest + H4gb temp — and fess polasdy g solvent favors elimi — pakon- — Lew femp and more. polaady of solvent- fowows — substihaber oe : eg - CHa Cha Bo ed Chach20# + K Bx (abst habs) CH3 cha By 2 OHO cs (Blinioskon} AB S23k A bulkies packephile bachgs about ehYminak yn ped trom atacking a tefoaualent —crsbons clue to Skee —-yeasons. B Reactton with metals. @© React with wa C wurty seacifony Waloclkanes — venat cotte Bodlium promo gate form alkanes . Clg? + 2a-+2ciy ee Disadu. © Wwuaty ceartCory gentraly. fails oth — Salty haledin sche under basce — conalifdonr gq fax tonekun | they pager to Uncleago — dehycrohalegenadcn — ko foe” = alkenes. @Qerenr ow ruiaduse g fe0o liffeaent” ally haticles afd Oseol, dhree. posible ailleanes Gee fexmed- Thor 3 oly dang B Lo & good melted doo tte puposnkton s —unsymmetete alkane . © Foamaton 4 nomelalicc Compounds . oaganie halider eat oaidy cuted malals to Yoon Compounds — contaént®y carton metal bonds. Such Com pouundls ae known as r0- metals. compocnts. ©: grégnoed reagens (Mg x) . Gownend reagents ae alkye Mg. hotels /coyl mp totscler Containing — corbon— metal bonds Coagano metal. compound) . These Compounds at obtarrect by the tentttong — halealkan. asta My 2» cy cher - Gis Br + Mg 4 > GugMehs C&R) In te G2xex t , the anabon— magnesiany Bere ry a9" orl 6 covalect, bu highly polos, ests cotbon ve laén 3 XN Cmore electoonegasie) | polling ARIE ye Boo Ng Celectoopositie) 5 the -magnesrars alegers bord @ essentially. forte Rage GR ase Anteboly weackve and yeact with ang Soma G paotoo to give hytirocasbons. Even H20 , alcohol, amines CAM — conveat RM9X bo alleanc. x ou RMg X+h20 PRY + Mge Le 5 theadove necesony to auotd even tracery modkttire pom graroe Pengert « On te oftechard tus could be considered GS one G the medoas for conveattog halidn to hydrowstons . 30) Bess Mg Bnd Na, alkyt haber can zeoef Me, Xn, Hg ete — presence of day Uhr to fear Coapesponeting caganometallic compocurs. Ns By rate PY 5 Cocke + Me bo Reactor of Haloavenes O Nuclempnntic sab R @ Klectaplehe sub R @ Reatkin uses metals LZ Nucleophtas substtlution _deactfons @. Haloorenes clo met canele: necleo phttte Substitudion — easily. why? (oR) — Haloalkanes eelago nucleophahe Substitalnr estly whereas haloosene do not . why 2 Ary! polices ay extremely less reattue focoards mucleepwiles. This & due do following reasons © Resonance eet Ce pads on halogen atom & B conyegatéon wh RG af 29) Dut fo xesonanw tee ia portial double bors) Chotactes f% Cx bend. Thaxjove at Ae frcule- 40 break tris bond. Cwherens éo — haloaleanet , no zesonana posscble, C-x bond hak no double bond chosarter and therefore 44 wn & token clewr eastly) C uf Mechorlg mm <9 “jae feta, © _vochndenwing at ofp pasitons a d a ou toe (So ton _ slow Ge a) ie we oN, iP ou bon n of NG? ke 2 f ft oor. kre 4 ee SO Z~— NY —_ a Soo tt & Posy Aljet 4 NO, gp at melee positron a ko 4 of iS i ott BS eo nge = ¢ Neo oN 2o ee oo ‘5 Re 002 4, ob ow & Pas te > ss Gr cuhy dor NG poop Shew ts qyect only at oatn and pera poston and not at meta, posto? BF As Shown , te presene g wit2e geoup at catho and porwr postions — waded thr eleclas - denstty fom benzene. xg and thus facdictates the allack g mucleopmile ow haloarene. The cosbanion thus joomed & Stabllised —throough —-7eSonante. the —ve cota) Gppeosed at ofp woth Bespert do ee substituent 4 stabllisect by Noe geoup Cohale tha case meta nuU356 compound , none B ie ony aka re cone ow ot bore adeno haviss —N0z gaour. The PRS oe Gooup at rete. posidion clues not stabilise ve Conage tos ne effect ory the aeauterrdly- > LT klectoophilic substttutton _ yeackoas 6 Due to reson, € clenstly at oro and pose pence ne. ap cohen, See fo mele posting GS eit? sg oe © oh) a Co eo Be “a haloazenes carctecgo™ “elec opiulic Sub peas Ee as halegenattds , nitealon, Sulphonatten and Poe clel-coofes veackons. = The ¢h coming Clectrophile geet © ofp postion. Housever, beenuseg, 448 Treffer, halogen atom has the — tenctenty bo vortradosed eleelasns fom — the benzene ring * There 0g. gis fomevhat didetuated 9a compared’ ds henge And hence eleelsopluke Sub enews ty Aaloarens cara Slecaly and veguive . move doaste —concikns ag Compoueal 40 benzene . O Halogeralin oO ® Niteakton @ sulphonate © Frieda —caafis renttrny @ Fc alkyodtoy © Fe aeglakton « @. Although — chloahe group, yet 46% elect eophatae % an elector esithdoaconig ortho ard pasar abeseetvig > Sub pene . explain Cv. vip) Ref Page 306. EB _Reactisn sity metals . @ Fine Reoekeo Wut - Filla yeah on. Renckion with Mg 5 Ce Hs Be + mg yee 5 Cousl + Mg a SI Colsd + Mg THE > CAbsledd dayciuas betrahydaopunan > used) Ply Halen compds Dichlaomedrane Pexpn, Poops, he an) chloaefoare ie Lodgoarm corhow tebachlexde pages s0e-309 Freons DIT “@ Student No... D brbath is more keackve_in elelagplule tub reaction, benzene ox Cholorabenzene Panay We z —— Toc _electooptulie Sub seackins, elecloophile is “looting €-rchr cankze. Tur chdorobenzne, Lh wthctoous @ f' _benyne ning I effed g cL) : Therefore _@ density io the nog decuensee . Moreover ch _eestabilies the fokeomediak _conbocakow (formed during elec! fools ___ Substitudtow Yen (ton) [cieiee ae Sree rs (by -L effect, ch nae a © eesti the canbecaken) No Such factors ae prescott b 7) Bengene Teo ‘dus the presena g delocalised 7 elettaons . Theayoe _bengene > move _Aenekie thaw ch{evoéengoe in elecbephate Sub voneldons eee ay @icl o aw “ electoow sadnelrausing goeep wget ab be & ofp olireckng _in__electaeplulike Sub deacons: tohy > @ foom 4 toe benzene xg Geackvates the xhg) and - destabilises the _cosboeakon Gl evo CR3CHy che cla By hystoegen, Bx—C 14. ——CH ==Clh —Ch By atoms should be oy wtvetins) ig) © clb—cl —Cle ls Bo OBA ow cy dy ® aka cn >. @®- crs acnon ._ P/E 5 ccm cacn-t CPD Coo treat cach ner [yp C3 Clb cl. CHa By ES Cha Ch. ch che L + NABx . auione CH3—Clh —CH =Clip Gn: Mas Rats) oe Ref -Nola wa@chal © chad Me > Bras 2 eo" Con) @ 2=chlo20—2—heayy bidene ude §—- 1B CI. Cl2. CHB que] NOL Cly— ch —C Mca 3 he major mtnok ch aoe gs @ vn Stent No Br) Student Name Thus reactivity & contoclied by tndurkve effect and oxentakion 3 —_ conteelled by wesonana effect a w Sauna ie @ (Bestabilases the coabocakon by —Z effect ) ses the cosbocakon, cy _resenana) 3: Haloalloanee veatt with Kw do ftom alkyl cyanide , but wity Agen foams _tsoyantie - — Kxplain * Chacl +» KCN —> CHa—cw + kd CHs—nc + Agel Clad + AgcCN —> The _ bond betwen Kk and wis lone ~ Thajor bey 'C and Woe [ree cowate & pair. But c-c bond % More stable than c-w bong. Therefore GHaek takes place Hhreough ‘ed atom whith zesults tn ta 4formattow of alkyl cyanide « However bond betwen fg and cw covalent _ancl_ therefore woth rerults ony ‘wy’ free_¢o_dowate _ @ ~ pair 4 the formvattow of alkyhidfanle @ ® @o Kxeust (chap 1) 68) Ce Be bn > at: Ci, ch —dH—cls — calkyt 2° @ Cliscyig cH GH) cH Ca fa fis P3CH2 gS Le Gy. 2) cheb CEBL—chT — alkye A Eire cng ce HS (bengytie-£) e » chs—cnGiis) cry alkyl 2° Oct ¢ Gis), Clasy Gilly D caf ecus altyld cinch don. goats Gus Gngio® Br fae Cl3—cH CH —c—ehg Ally! 3 © ons r= —

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