ods + alo] A, me Atcts, Cae 1ecH Hts 4 CoM ——> GUsCH, —e GHs§ SOUS ea : ALG ie Gps? Ass (owsycw A eo CUy + 3GH,A44, Ph, Alt, ph, aids tl. CD gt Loa Lo Peat + cHoca HS OSS eu ph Meche wasn ; Colts a H Menthe gg Ht Coity CyB cH, Pa “GH ius i eS Oe a Yi Ean ~ silks oO 48 Cc eo ee Wl 4 moleicankydstde Vos Polat Os Sa Regt4.08We Camobienzs scurat Chfeet with ocidsfied kindy During oxdation the oclive cuuonnatre ning | woe. rnadluarphr: -We is oxteliced IF Alkyl group attached fo Bemene xing bas atleast one Yuyctogen ede. with bot alkalnc KkiMnd, 9h salt OF be ss Ut, woo ) nod C) ak foe? Kt 1S (ow " or —— fo] gt (07 @ --- B 2 U5), , ce medi lor, CHy- C- Low Vetyrigh an Temp ( veay less yieldvole re O Precnzcr, * @ ci pith — crt, Ce: Ary, at Cia Orie aoe ‘ t h Ee P Whatnapp Qs PacHee, —PrezenPh , _ELok Lok vbr . chal BO me Ad w-E-Ce + Et + ph—cecth 4 10% procec—th Saget >< a on oceans - ans Ph By cach 92 cuownate Phe on A (orc Hay LH rt Bae emporio°% Lorain toe, S%4 at avho| pana, cdvophilie cupstitudton poll replace Ibene vee on Nh 4ions +ner we Ougs nen aly Ca, a wee > ts, Os BIS et 710, nts ane vas, ee ocd 460% LaeElectrophile Typical means of generation ‘A. Electrophiles capable of substituing both activated and deactivated aromatic rings 1 O=Nt=0 2H,S0, + HNO, == NO;'+ 2 HSO, + H,0* 2 Bry oF Btp-MX, Bry + MX, <== Btp-MX, 3} BOTH, BrOH + H,O* BrO'H a Ch; or Cl-MX, Ch + MX, cl,-MX, Ss? CIOH, CIOH + H,0° ClO’H, 6 S0y or SO,0*H H,S,0, == SO," + SO,0°H ” RSO,* RSO,Cl + AIC, == RSO,* + AIC” B. Electrophiles capable of substituting activated but nol deactivated aromatic rings. e RC SOX + MX_ === ACT + [MX pel” 8 Rt R,COH + Ht == ACT + H,O 100 R,C*CHRY, R,C=CR,+ Ht == A,C'CHR’, a8 RCHX-MX, RCHX + MX, === RCH,X—MX, 12” Ro=or ROOX + MX, === RC=O + [MXqib 13" RCOX—MX, RCOX + MX, === RCOX—MX, 140 RCt=O'H RCOX + MX, +H" === RC'=O'H + [MXpub 18 ” ie = RC=OH 17k R,C=O0*-MX,, ReC=0'-MX,, 13 t=NHy HOSEN + 2Ht <= HCt=N'H, C. Electrophiles capable of substitution only strongly activated aromatic rings 19) HC=N’H HC=N+HX S== HC=N‘H + X- 20" =O" HONO + Ht = == N=Ot+H,0 21" ANY: ArH; + HONO + Ht === ArN*EN + 2H,0.dy. Nucleoptitss Hubrfitelt yn Nuctusphite awbrtitiction over athe aromatic avyitcn proceed through oth univnoteentar & bimotrutor po-th Bimotewtar_wurkopilic Aye fhatidu wien duatid wilh sbung pore “ke NHr proud Hrough suckiounediate substation Formation OF Eengyne & in ROS amd akabi lie, OF juortlua pony mien depends On -I effect OF athe qedups Te leaving tunduney o the halide Js the por! OF Ros ond frumce with NH, ool nly the velative val of 24a” (ArBe> Aue > wee >wF.| " thts r ie pane DE muchophi. jakus plaw over Onna ' Gat F = ed qoup. 4 is Ipto he substitction on adkjaceat caron 0 your © cine Substitution \ the Yow ine gor i, <0 NL tax oN Nuch omiem ln Pobitod Aa e@, s $1. Ne tt (slow) Cope sor ant wale 0 [substrats oored |» Himinahion -addiion type 8 on Orden =2 (Ay sn)Alte fi ‘ mH H, Gl _ of + NH ©2104 cn, Ny) N tr Ot, (major) Y e es qi Nes He i 4 Cs 4 (wore Atadh) a t Not oj ——, eo + Natiso, AcN, S 3 ° in es MONO, hy = oO q 2M — CI pawl amo nitkallic compounds a4 lors un apsotic an : daoyen a deminant {aco cc, ne Re inp ave yotuent otun Fr F ie I ui z ow ie tof aq (IE) ecc &AMD. ALiynmatinn Keanteen Lor Autbitibalion Nyt bot oAlniil onafaulor Aubititotion.ioy ocld”- deni nedn “pall wilh V-eompler an intirmedsial. 2A, she add af nacho lesb Oven @tovMiasic finn @ -uachavge & duloimedia whith in ataltlesed Only by pruence of ewg ab Onlho, para pocittons, : Nbscence of CWE dor Anutlalidu doan' allow dubeltkelion wily vlog! : 7 sak L oe a Ley oe he aeaen, OW Nao iebatin © * hoe pe Dow! procese 1 eg alto (0 nou! = ~ os ° eee L 3) (Oye NO, No, A oun Ve ze ge ted NO, 7 Yo mu Yat. «© Cubrtrate | [ney Oris = 2 Addp etinsnation azge ( raven balons opomPenters Chom as seer Ole, Core sweaty (Lay Be nr, ere. btebd vith, Verda 15} aapellicl a teLawn g endeny of Wate is not the post oF Roe but paral ave charge. over the cc” fa attacking of quchaaph'k. lide tne vale Wen Aye > Avct > AeBr > Aer 15 > on KEV sey COSI + Pw NOs NO» UhO~ Sree cane Abele factou Os combat carbon douot allow) Budbetition DF EN” e € a ay, fa" uh @ reactivigg for Aven , fo, No, — (add.itton climinaHox) r¢ é Vole 2 cane CN, 60,2, co,2 60 X comb £10, 8,7, ArO.An AL leaving qe b Hee post OF attacking Macleoph:l. an subebitarens, tt 1 _Wicariows wuchopbulic ayomnatic eubsettation. this proceed by présence OF rong eng over benzene No nO moh, [0 0 lee a a on ue Nia,NO, ~NiA fo * HONO sek, ws ty hy , Alouic Inbile Vion CARA Claaaage lr plane ONS & oN Ragan Stagfe bord clusack y 0 hho xeac? §— ery uh ser Ch - Ay c ce F "Tel ‘es, Ye xT, ots ips te e e ! ast @ Mater ons l 3 a fey Greqnardi acageat W2-ditatomenes reac uth My [ey foun Bengyrre Raythatides can Keak wrt, b to (ese Guqueads aeagont ror” ual ea a mqce wt, [uty . Clie SL) ea at w ialvogpnduan ALG Aosa Nn pos 4 uote foo Phan «cation sutovudiate - This pote adlalid. with. cons Ain ane alep vs te aepeedls only on com of Airyen § Aeageni < sulbibitution (Aven @ sewh = o Ne erm ee COS Nw benedeni vole canst] j rds = if oe Kei fe as a @ a 306 He _ fs + 8a Solia oo fel Nano, oi Zof na (0 Fe Hu OS™ FejHu Line ene Ai 2,06ury Diayohato bhenas Clitenthe- NaNO- el et HU,2Se Ne ‘I We fol ea iad: Bry! Proence of bet. EWG awh EG ak ontio, para potions duoveare nae Of acace due to double Lonot chonata bfo e-N Rig a ip alin eae At uly ty panne athe eppeding @ at mela pevitons' a ow H 5 to Q fc ait ; toe 2 PN ie ° Ne eS i to LAD: 335 ry w-0? 4708 @ Wo-neo nO-neo == O+ N=O ’ Lp Caos ; Co ha, HBO Gea -0 a Cte #88 4 ¥ w A @ ! “ aN ee (gHHeft-N-OH tushoh > GP SS ARO Cots —N2N+HO oi &e e. Glue, “ oat oO +N, FRG ee Galter maul x20) are tN tHe N ben tpdbee! ? ees a end ee fe fandenuyeds aeact psi Ny Br 4 Catn| HON [oa CO> en neeut , Y 2, ler, ! cram Bale abun nts mo Aes uae”, 1 a yy 4 kOe Corded on eee sl ne Ome 7 5) corre f° oO LO? vache Pow c% 1 am ae woo i veg, a fentlow a ” on el owe, one. ly. ch, J ol) ee Gh et te ay” : (Reactintaied tor aroma ‘rmnprnd Gatien rurnaplaction contatnany eq) Leacr of Gee wilh HON § qoseous HU in paren. OF Lute aud, imine e Mliymediale whith ards Vuydrclyses 40 yield — atdururles “i Formuylation yy dake pla at 5 4 lst i orileg. ei aa pee potion if px compounds conledwhg Bag. ‘ \ACts cto yi (5 sa Madan Nee ON 4 ne Alle, 4B Pau, Q vi Hy / GENIN accel Hen Mn on fe) es ey Rey B) a) vers Bd cy " IX? Als [8 + (0 {#0 (0 Cajon Q + NH Ye Bele and sid veprllorts dorm awe jail Jor arora weanCl HONINCE Mts, (rage nen fHcl HO “Alki HEC 1,0 Henle, Addy th 2, HON is frighly pasonous & it ic suplaed by the use of =EN(CN), in gaseous HU whist the byproduct zach, sowe an tows aud - atten echet tym thud. Rear? asematic ue's with co & Goreour tice Am pounenie fo Alt (las aul) gives anufl aldelgches. this xuac* glo poled by pune Ewg Oo + (oem ha At aM FH sn He tha 9 10 tH — |, C0 + OH oe Pema. 1 “yeo i er noes, O» ois or @ (Owed Lay eg eee Be Oy as ais conepr) Chloromerrytasiony -220 % alfred Bee vot ond His “ie st 3S Rusards tp} oprWhen a watioce of benzene vapoua ont ay aud Hee pared Our Cull, A colowiless ly Unlovobengune it sored (Raweligt process) ces HF He tig Sey adn UUanar's rear Couling Of aryphatide, im patsente OF Gu to give biphenyls 1S Ullwans seace Rok of Ulnani sae” is Wore pr LT >By > This xtae” ic abo exhilitcd by onytihiouganalas x B > Orson Cg Het $Aln —Coygla 4 Cut Glee + Conc 4 Cote — He + ul Utlmaws neacr nak int by pasene oF abel , along 4seup at all. poscttons But pasen® of NO, rly al oatto poritron strong athkivolis Aeac™ But pacienu OH Nth» NHCHy | KHCOGHy , coor fdebit the ale ab all the povttiows tne Ca Catalyt in Ulmand neacn coun le xeplaced 49 Ne. om Dphenylarins nite anychalila purer Hes 1%, wrvertid to 3 amines - the Solent for this proc ess i$ NitrebengeneNA+ 2(uveds 2GUET + Ky, G5 aC) N + COKE GHCNHCOH, 4 CisBY + Kyo, Y, Cutis NW + cor + Chk, K + RBY CMT +O, Hla, Cong -3 ot ledobergenre didlbovide Ghe -T ‘0H, Gls L=O + Nacht HO iodowbenzene- wo'e_ (01) a ~-I +H pee hi wy mek Fart ‘ ; eh ver Na 1 9N a pn +N, cath + OT ut breWeN 4 OU” oy Ay g Cut 4 NY AY + WU > vet + Hos Gt, — td A a tm Swwdlneiv Cu ovulating tn ta] tate oe als Mu 4 Ny ee gata an's Ss hrGe + Ny het 4WMackgartny @ : - IyeNeon Ay 4d GH Ae er dat Anh + Tn Galton) aac Oo ts ocullaking bw (F162) ® @ AO _AfO yt pyr + Her, + NAO Who i Mickanten i} F 8 : a4 fy-Rene” + reo 7a shreN be AX + 3 PO{0") int 4 PA[0)OK fea nytt Pu(ojou Anh, + Batotony YS $ (oyion BAN, Hy0Q, + & Reacr of aryl hatcdur vith metalic sodium i cybe hers gives dihenyls This is Fitig teat” GHsBr 4 9Na + Br its cane Cols - Co He + 2NaBy he rune fd aul and alkyl bated voit jute No in eter ie Wools yittlg xaace ‘ i ales Gury + oNa F brCatc LE Get 49Naby cH, = 20H, Oy ode Upettot =a, (Wbyoann seo")| Oe O £ G44 040 Shak - sz (5) a cued & am Se ie ‘a Sy san Ho ay Se - teh aa (of m5 bY js he OP he gen tbat acy He} if a ‘20 3 a , ? oy £ 8 : crcl 0 > Neoor : HG od y 3 eine caer Lo) psn Em a SES cgi | anlPets et Soy os Sis, 4, Henig, sheoeon0 [Per2s, ogi y d st a & t cof i “ of ipenor nics ae soot + aryso, Lr (OL + ases-atoxsi0n,9 BE Kray 28> diem fon cea Cy A abso” Hb R wry Ste owas Kms cornmcner? astoaratin — [Bs “eae ee z Kn x ae: G&S oe Os cx _ ra J rattagial micecx No, We nos gus * OMG, () Soy. " * 3% & EA sac y Re, afar S o \ OS CIT &% ¢ reas oboe “uly wa fe alter Kole ek ac fe xt Red, tx |S, (ofa ew tire . ans, els, 1, el ots, ot set ine ce \ ny +O, ens % rom wn)” Q gts : 1» mo 0) (0) a) a Cande 950; |? : Ocutind: Ecbe OL oxfdarforn =f al Baoy[w yer see * sb . pee CHR, > WR > Ha, ise pps fe mer Art, ele fie, —> Ar n@7) CO, (Chromium (VI) Oxide) ‘The cleavage of C=C bonds with chromic acid is competitive with oxidation of allylic C-H bonds, when cyclohexene treated with CrO, gives the product cyclohexenone which further oxidizes to give adipic acid as the product. eo cro, CO, COOH .COOH Oyclonexene Cyciohexenone Addpic acis The use of a partially aqueous medium favours the cleavage process where as an anhydrous medium such as glacial acetic acid favours allylic oxidations. In addition cleavage is promoted by the presence of phenyl substituents, evidently because the first step involves the formations of a carbocation which is stabilized by adjacent aromatic rings. ORB [OE] ae Examples of CrO, oxidation of olefinic compounds. ” HsC_cH, ° : 3 C105 ° [ eS Te eng En ce H, a ee ts H, HyC7 “CHa 2 HAC. CHy 9° Dt on ere ( ee CH, * Hye Son HC’ H pies