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    Diwakar Patel
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    All benzene reaction mechanism

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    All benzene reaction mechanism

    Copyright:

    © All Rights Reserved
    Download as PDF or read online from Scribd
    Flag for inappropriate content
    9 views31 pages

    Benzyne

    Uploaded by

    Diwakar Patel
    All benzene reaction mechanism

    Copyright:

    © All Rights Reserved
    Download as PDF or read online from Scribd
    Flag for inappropriate content
    of 31
    y Benzyne> Be ek \l5 CeHu (1,2) -didehydavbenzene — Also called = fryhe. Ny IS NQutval Reaction Tntermediate - i +, Fromatic in nature o aan TeacHve Intermediate. because af the > Presence Shrain- g) ——— eee eee Pee co — Benzyne Se illic in Nodure 80, tt is_abbickel I 7 by Nucleophile ives Nucleophillic addition Rx [ewe See . 1: From Halo benzene —> A) “In Polar protic Solvent :- ae ire. 720, Nig NHa-R ,R-oW etc x Nant, Hens or”. a i eee eee ea og on al ‘ > re Tn Polay protic . . | ees ° > RDS. —> Releasing o nr and Deawiieg OPC eee Here 4. anism takes place . Cc } feng CF,cl, Br, ra Reactivity —> Br > TP a> . °C | B)* Th polar Aprotic solvent 3+ ° | be. (DMSO, Acetone. Acetonitile , oO Cc j So | Here Step wise mechanism -takes pigce- © ° oY > oF-O > GC Po” re Cea) Ge) E,C-B mechanism © & Slows 7 ROS ‘ © Unimolecular Conjugate Base Elimination. o © | c ° SaOeHOHOM HPF ePHeORHOPheHKPLlOe PRE LLL x CFcl B4/E) Cle, i eyes Relative Reackvily :~ From Substituted Halobenzene — Conly EL efect of Subshiyen 4 Para -Isomey z Zz cor? x, w nl T Dee re Cc Pr © 1° 1s mo 3° We We We ae aor on 2 ; NaNtta. d,¢ = oH eeau @ iI : ~ H,° (+1) oy ae ‘vets 3 E: a a a be CHL) NP PUD ° { GN _, more ncidic) 1" 6. NaNis . | wl cc) 9 i <) uw CLL LS SHEPPRPPP EP ETP SD HP OREO HM EO HM HOH HRHOLCOK HL LO LL \ NaNho > of © S . a : U2 © | c i i ° | ) di Halobenzene — ° ° if He ae c | Oe br | sfinetatiasion Se, m® © - os io 4 jn Relative Reactivity oj Metal :~ (X= Fl, By, L) were eeooooooogoas ots © tw Y a. BI’ Rui 15 TBRF veeee 4 ‘ CECEE CeCe eee Oeee e.¢€ escceoccecs Je pe eet ee a ee ee eeeeev ev vn om = - |e <= ece From aAnthranilic Acid: _— Nia NaNo Hel pt 2) oN or f HNO2 3 i S)) cl, By, 1 eke YL Naon cag a et o® iy 4 —Cor =a A NN O°. Ge ~ \ No cg =" as So Sn \es Stabe cpa Form ak lone em’ Pb (OAC, 2 “ORS Tee S) ie uP Diazonivm Salk Stable af 0° to Sc as-Tempy es to S°C Na Rekase Autvmeticably. oT 4 ) é ©0900 600 0 OG © 0 Oo Oo ole +t. ® = a Q _ o A vecoce WS Ove 0e 06 6 6 ———_ gxz__—_—_ —ZF___— | |__|; 7 Fi SD 3 Pee eee ee Ba, Ny Na i © Suit 0 wy, Ny \s mr ( u ty te Tis Coon Coon o°% Ray ee Novy Ty Ho, ‘Hitve ‘at se : Wt ro i" 6 non, ee ome nt} : Fone opm ] i it - , ane N ’ % ( ) | iD (Hf wv © ( 7 : “J WM) N A € Le Dimerisation and _ Dimerta a5 e ei oy /. ¢ Y gemane} | PAC GO SSSsSsssSHUHPwUUtUUuceLectse cles ¢ Timer ay Lf a. ; 7 be self heaves os the dienophile. _(clectronicany : Agliciond Species) fn, ur valll Reged with here ( wn ralhy r ich Spe iven, 5 q Rich 9p-) and gives Delon Aldon. Reaction C444 (yelu adn) co vu Yv Den 8 [x ' oo ee ae BA y om ao t | Gg eas OM ] sy : A 1 an A — > \ Ss 3: Nucleophillic Addition Rx PS Since Benzyne js electrophillic ae Sy Tt ip attacked by Nucleophile and gives — Nucleophilly? Hon Rxn- Ey + ew mechanism — eo é 5e CIR + ~ CM if | Nucieopnillic Addition in Substituted Benzyne> oS G : °e C#t) © “ea Co G Cc i oe WW OO COCECCCOSOGMOCGOC OOS mojor ome. ae \ 3 or “ 4 ynojor ie : AO a Oo 4 Nanos tHe) 4 >) Fy x ais) @ HO Cv r ° [ ye ~ o — S 7 2 @y J © he oO Le "7 6 &2 4 Mg-Hg- i Mo er as IS o a a ye Ge ons lo yo “ 2 i) wg OOS oo re we > B a : soy Gh DME 2g ie . l2 +RLi —> Ce, ann a ‘ uO AC ee p iftimes \ e v cB | TIFT FT eS es ae cocoosc EES cit Work uP ® Nhs oo 2. ® aH. 6 ao Cu Ny a | AYO 7 | ay ~@ | Nanha @ Nata \? = Kc | = : CHgCN ~“ i W wwe Our— CLs. Ga cHacn + NdNH2 ——> Br, —en cho [Ht Pee Hono [Ht cy CHaCle = P Pha +FBxy Bali Hao Oo F PRL /THR | = then. Te", VSO ov vv veer eve ce cece v Tv , y VIF FILS TT TS ee ETT TTT een POOCOCOSLOOSCVODO0000& 0000000 773 : 2 ° $833 é ie zg @ & i = — = iy S : a | Ph cmH \ | PPhatcBry Bub Ho P| CG SN Ro Pyridinium chloro ——O Ss ‘NH cy Zz To 8 2 chroma) dd Loe S ey iy Pd-¢ > a — as A—o— it oe pr Ri cD Sy 2 Y, 4 Mal onote ester avy ~~ 7 © 5 abe an il LL Naw, 9 LO 28! ; Ge + eto oet ome & br " Cmatonate estes) Gj solD- ome Doe ae 0b uy ZT 4) | Wo Nei — a ee Ko iy @ *~Ncooet 8 Ss wv : we ome” Ke ome. o¢t at { Cook i) e A a 9 ) cst qme ott ° Ou: thane aes work uP ay p « WU) Base > mee) oo) oe oi oi ee i ee io i mei in io in ign fel llmn COUie rr rTheesrmeerawi Fs vee ri ee rs riers ae fan VovvsyrxVv2xVUUUErtUlEeccececee VV ec Pa oe or < b=) Ge : goo , : [ OMe ® Oo Nome ented | SS acho “ coat coo et me ey Por eK a Oe a : Ne ne é oe ; i. ° ome. | 2tlea 101g 1 oe pn | —— omom < i Los est gon’ — thu Om Lg | oe ome _ | — We vie [18°C ® — ®-—- af “yee 0% : Oy Pre Crm © S256 ) so Qo0oao0 eooooo Ite SSP PP LRT OLS LPOR TLL LES veceee i ° ° a ee er ee ee ee il Qu Nucleophillic Substitution iN Haloderivatives .- 2log}zo1g, AY S q Hatod erivedives ~ By By Miphatc saturated Halide 1 frul Halide ag Hie ~ i a ee 2 oe omnes a — tou ir XS v 2 “J Weak « bond —s ze 4S, a a Re a Fe: Pe: bond charades ) ey > cee (Partially core] : . a i (Bond characte ‘ ‘ ~Nue 1 a ie aN x ’ A ao Vacant ff 5 me = ae Blechonic tI 4 Repuision. a2 - 1; Apo L 2 vu 7 SETeNe TT i ees \) A 9 FB yg — cH = C—— CH Hg o b > CHa CH Ee cy —CHy Lequi nue Halngens! : Halides gives Nucleophillic substitution Reaction. Via og types Y mechanigm Ya Na Substitution Nu® ArvSn> Mecha nig rn +- SCS Ba, Tpso Carbgn: Cy es ine Slon- \ Roe Ypso atteek— Sp — Sp? Addition Hep ArSn2 Mechanism —> )r Ny a Benzyne Mechanipr, ow Cine Subst huion or Elimination — Redition rechanipm ee ny G5 CS 5g N Woe) co Meisenheimey Complex eo ec. ° oageo oco$o oo ecececosd Wreceerererereeerrerereeearsrsr essere 7. nin a i aaa Rate & [eotio-e lJ LN) tol Jollow Second ardey Kinelves Te is also Kla Relivalal Complex Peebanisny since Foleymediote Carbanion ts form in KDS+ Ho, dy nte of Rlecben withdrawing hp. in Mayt. Hatide (Yes lve We. 3 Pays Mechamsm:] Pes the Reachivily gy Subslrale « ? PySpX mechaniypm 9 ‘ ' . 4 a nce Ss Bw o |p more efpective When Ut Vices dhe w ortho «4 ~ fesi Hon cot to Leaving gap - v Se Th Mation takes place. in bl Carbon. and—~ mC Soom nue : mo — pa © Que Prrange the following ae order af Reactivity— ye towards — ASN we 50 “1 a a i Nop. ee oO Qn Non, ai wee ee eee z a v DE f SSovvvvvy v- i. * Zz z 0 e Te is also Kla Activatal Compley mechanism: May SS Ry : “i cy Na ey u a = a Rake & [colts-cl') (uuO} x ce : uy . Sp3 -sp2 ' wo Follour Second order — ee MI : elimination kineheg ole-4 inte. Fnleymediote Carbanion 1s form in RDS- Go, Bw of Blecton withdvavsing gop In Aaj Halide Ds toe, “fi Prd mechanism: | @e tre Reachvily 9 Substrate 9 firGNR mechanrpm Le, 3° Th nce.g) EWG 1b more effective when i Ves Whe to Leaving gep- * Th RD-S Bon fien takes place. in bls Carbon and—~ Focoming Nue , Que Prange the following en order of Reactivity La Wee eee eee es OH OME EO EK © | Co towards — ArSN2_ mechanigfth + j o cy I G a u a 1° G cor™ fo} Ml oc = BY aly « Cy Nor = A mgt el. a, 2 Non, = (B>LY29495 qe es DH * & jee i Boe a ° Boe ye Boe x Nu Re . | Ai ; i { | : Ex $40 . Noa, \ A ee + Lo \ equi . Nu 3 Mo, ine & L ° & & & (oye on 1D wor : 2 eo . —— ‘ : by Loy a) F - = ° J q Note-2 | \ } | As the Blectphiliaty ey Tpso nh \ ‘ { Sor Reach vity towors — ArSN? J Rate oy freon spl I 7 2. Rate of Aesn® Dea Reattinily a Subst towards fron? (Des S St o | ° Kop) 5 9 ‘s3 “< No, Now Now No, “] SS ———_—_ CCG | =I effect o Halege Ges Blectrophillicty J Jpso Orban bes | i i | ececcecce eoecooeccaoons >} Pr epee eer eereee pepe pe SP Pf eS W , | | id eeu. Bee ee uu REET Eee e oD 4) Gat) yy) chibebin Reacton > a) “ ‘ul also The example of eS? mechanem US in pyeiding 4 Qyinolingt TaoQuindies- : = po ———_» |i & bi uy cM i A wy" 3 Wo Mechantorn .— Ch ° AF ya i 2 cs GH Ns Sp?—> oy yt @ err A [ Og, be ~ Aa ty el) Gem a Lal Hy ice D Vs 9p — op. = 4 Elininahan Pin Rot. & Ca) Cru? J (Filow IL order Kinetics) | | g | ead Ca. 3 sequi Nu® eu Se Ry JO. ts “J a ined) dequi Me sy pote ee No Rin — me me = VO @ Men 1 N 4 fy 4. . , 3 e © c e © | Co i cy iv c eB } N : ca a . | N PY co | S8rn. cl a — NuS 7 Cy ue tS ae a C ° © Qu Arerarge the Following mn Usiy order 2 by a towards Teenithibabin Ren ° ° ar io a fel ee j \> > Bou, : fa =| © ° ~ Oo a Sy SH ma ° | p32 ° ° 4 1 ; ’ , f il 4 ba il 4 ‘I Hi il i! il A] il il dl ‘I | | P vo akk 1 oO _%86 Ps Lewei Nue o's ae Tne > ooh : J] vo G ~~ oui ue “ee ¢ ANAM Rs NS » Que Complete Pre Tollowaing Ri a Im . ee eget ~ il Fei Mu - 7 4 ‘ : i Neo we oH 7 e 3 4 | hy a Me ay id - ad tow 1 " Vy, Ae suet r ) . 5 ls ae Nu a x oO / a: ; ie Qe i of ery. W Poke ray > > 4 2 2 a a wesee ¢ — Y ge ow feu Nude AL 2 ors 4" OD © SN SO yo syeeeee eee mg Ir Jd eayi ud : \ J \ 1 y echantan Whe Wu) ned ape | (Kou 4 ' (ne Nagy. Nig, R= ity) : iy So \ ( Cine Substitution) S—~ \ * _satiita,_ a) OY Mechanisya (kxee ‘hg ececce i } : err nabs + a omg l | _ Nana KN oe (OW Onin, : i= on ‘p ° Car) i ) (em) hennyne, Oo, coy) . ( ; Z sy ered 6 7 Fm ce 4 (eo o - Hi \ 4 } Nh + MMe _. 3 “NM \ JI G 4 (484 °, —— rere! 2 fF € ith fov_B enayNe Mechanism — LY EL Presence Q ’ oY, , Presence g) ortho H adom wwrved leaving SOUP musty Requirement 9) Ahong Bane: fe~ NaNla , Buti, LDA ce iS alheence 4 (owe a tn the Pubsfrate Presence BRO COR, Cy we) In the Bengene Reng fees LER, tHd iS & ¥ CDy ~~ on, —or ele nee |. Que. Set oC a) ue AY, $y) _ wo im sO étoNa mw up Nog Relative, lan, S ws Ree conkeg is Ps. NO een | S re: Oe Etoty ( Nani 2 ANH; aa 7 o _ Keke Kad ty A) Ky> ka and kod ky Cepy QO wa G@ Kook, and Kg ky bp) Koka Nucteopil Substihution —> nat 1 nge a RNa AL: Sub aleale. ao ' ENatine a) 4) Substrate? a { ree ~— Avomasic Nucleophillic Substitution Aliphatic Nucleophillic Sub" oe at fl Ceca NSW Bervaymne. cD) Sut ey? Sut NUPs Mech | a Nog wee or Nano tke! Colazotisation Rxn) O-49 6*c. | Replacement gy Na from | sé ArSNE Cunimotecutar Fhromotic Nucleophillic Substitution) — —- [ Benzene diageniome’ Saif ° oO PPrPrePrprnvenkeeaneeetnr Q Oo ooo0oeos9d Ren « C > Cc Presence @ ERG: In << >» the Rode}. “Diazotisation © eo f o by Nue Poo ooo oO eoooce oosg a ArSnt mechanipm —> PAGS caer ie . ' NEN cr® al + NU® —__, fog. iN Mechanipm ‘- AvSn2 mechanigm- Maolh COT ROH/D OR, 5 [x ony CS" On Kron or foun, °F kd ae. aS opt ee \ an =uel oy 6 so cot om fluorit Acid: ET zene Diazonane 8 Ty a) Bornftuarote oo (B) cod oy Here Free Radical = oi eos) \ is form onthe Guay bua Ran “Lnterm ed iccte Gaby VBE {o \ & e = ® J Ciro ¥ By ~ — tae act tle or Cua Cen), Fon (Cur Powder PME ~> qr: ~4eo ° G Cucla 225 cucl + 01 S40 OS yy gre es" Og th vol acy — (CW + co SNS" Radical aon ( Benzene Carbenshile / 0K) Lecce OW RIS ; ! TT | ~! © B Reduchve deamination —» Mia, a > ic HaPo> r oe Es @ se Qe Gromberg _ Reaction - _— len GY Asomatic Substrade- by benzene diazoniven Salt a Gromberg Rxn- ee = oe matic Substrode- mechaniam ;- plage. Se 7 , a 7 co nbd eA ted i c aeeeaeee: 7 Be K+ ere Onn lo - [> °° t |r vo oe ce van Vo Ls f | (FOReplacement by —NO, Group — ] i Mechanism — ee! @ we . ne No BFP cs Pode em 1G, “hs Oy ane COS HNO. 1 Nog Sy Gigo:, Coy Couftin: tion —> DAMS sor =NHe Sere. < —Nme, Bynen ye Azodyes - til c Wo. a Le ae a oad ernreawrnre er ao Ln eRe ee El echophile Nucleophite | Slow 3 RDS i ; a 4 7: Fast oe ¢ | Oyn-N en

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