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Organic Notes - Compressed

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16 views128 pages

Organic Notes - Compressed

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gauransh352
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© All Rights Reserved
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x{2) H Pg-48 nibNGones ore eraikynes ez om “Chemical ws (56) ‘More Hs (60) 4/9) Sul Ery Sms Er Pa-63 ww ITAKT SY (C3) ne + Mulley bapes Cs) * Nucteophites and bases . wr x2. Qe C68-} X14) Hol eactions Pa-65 *|\8) h Pq -1S | * Alcohe\s C15 | + Ethers C92) Serax Cae) : d ay) som! aoKien CAF i Hadrolysis C108), BER eis ion. ag mm _{usrocobons “a Methode of preparation of ALCAN Es — = ion of N ALKY NES Csyn Addition ) SR chee — 2 cH -2' R-c=c-@'—> R- CHa -CH,- 8! ° Reagents :- Hs (reactant) & 25"¢ - Pr + * T£ Raney Mi icuced Cot high temp. D4 = i nd Vere wo un =a 3 aE = 2R-% + 2No — Q-R+ DNak Neynigei paargeomssngidie! Nethipr Appraie’ BB ° Reagents: Dry ener =a 9) Corre y- eT esis Cuk Rox 2H, p21 16 + Lix = Rocuti Lithium diatky) Corperake —a a | R-R' aoe = Li + pe Cuti doen't veack with —Noe -cN 3Co, ete g-thHa-e' +H Re o = R-CH , 4 wage Na) 7 OW SoWeny ; Rengentis Hydrazine Cutts : ; Cethylene & Ss ware- uk Ly to! Chr t-pg), pate 5! Cover 8 Com buston +. — no LCotisns2+ (intl) 0a =in (Sasi * Haloger 2 Rt ¥a Seeege Rok HY oor © Reagents = 1) Chinvination — Chalhy or Sorta | R200 =Bud-C4X or Ch2/ Rede 2) Brommination Bralhy or $0264.) R202 —— F000 br or CY. | PaO 3) Todination Trtho ©+ HN03 rH TOg ) Fluorinadon Fet Pave t No environment "Relative ‘Yield = Relative reactivity x ——Prooavinryfacter RYE Reawve Vad y 159 *), e oro ie * Heat of . As roof Stability of ution. 23 DATE oe Typ Sitthods of Preparation of Alicents — *) inch Reduction (Dorin t werk vite C L ‘ Er, T ) pee as OC Nye ee. varare a R-CHr-CH,-OW —> R-CH=CHa + Hi0 + CB-elimination) | Jo imhalogenaton of Alkys women | DATE os —¢-¢—.4. Kon SSS ee yon ; Hx eles de aE Kou /NaoH >) Nanhs 4) E402 / ELON 7) +Ru0®k® in tRuoH ‘) Pehaingenation of isinal dinatider + te she = ee eee ‘ — eee x CE> Cant’) etimningh on’) Reagents ) Na T in acetone ©) znidutt, acetic acid: ot Ethano\ > ee eee DATE _ Methods of Preparation of Alky mer 1 Dehalogenation of Tetrahalnalcanet ond — Txilaloa\icanes x ¥ Te Zn dust - Rocce et Gee orion, eae, Alcohol, & xX * CHCRa + 6AG + Che — > CHEECH + 6 Ag CR J_Dehydromeingenation of vic ond gern R-CH=CH-F' + Br. - ‘ork H Tue ero Coe R-c=c—e! + eNaBr € ‘ i = DNaNnw ot Br On oa >) ale. KOH 3) + ic a DATE es CArmMa® \e = "Rae Sc= hppa Bo CE City X 2 Ba RS EP | ec Sen SS R-c= coe *, R-c=c~e' 4) H pdidlycic of Carvbides "CoCr tH20 — Cort CaCOH)2 * _MgCa + Ho —> Crt, + Mg CoH), > _Mg.C2+H20 —> CH; ~C=HCH + 19 Conds S) Ko . CHa COOK aces Ty \ 4 oo CH2-—COoK CA => WHER F ra Be 3 ' gon, Ge uci i NW) CH— cook CH ene ae eee: 2 SE » ats DATE = on £ & Ye Willie. ° EX 7H enue i He H ——————————— Cae* Z \ A mS Reagents? iy Hx CH*) *) Hoy **)) pedi best YG OO i) Hoo/ Ht CHt) Ha Ogenation of Alktene XK C Nceet + yy No 0% Non, — Usually ant -add. Reagent = Bya> Cha Fr and Traore not used: Solvents == i) COtu Cregt) i) CHChs C Hin, mheOH, etd 3)_Halogenation of Plleynet Sr Br gy ssa Dp ae te R-C=EC-R —5 @-c=c-R — > R-c-t-R ee a Oi ee Be Rate: Ci)>C1) DATE et { 4) Radition of HOY to Aleene. { 5 on ooo Toco BOX SS eae a x | Reagents) Xa tHio — Hxo +HX 2) Hox 3m ) x OH Hox. 7 < deg; C-= CW Ga? Ro tmen HO X H “Tautomerisa= Yl | -Heo ton ! , Ero W O- Clo.) 7 Caer) OC-Raloketine Ob) Oc- din aloketon-e * No 7 =H 7 4 On W20, R-CH¥2 a R-C-CH 2 R-c-cHD Wy oN On m0 o_o ee eee eer! Vane x Cowaee aveeteeied DATE =) + Wien only HT, HBr HE or HCA ore weed, _Gpkisnalty in dasknets). Haan iss Mantewnitan hy 2.0 igh a Manleovnikey = Allcyner: - ge \ Rr 1 R-CECH — Rte eke. CHa x 1) Ahi -cditiyyda dda \)_for Allcene :- __nenitutaortodicg’ Et a7 TESS ery cuca We, ge (oan H_oW Hartovnitov addition and! Reigorelettver > S ” Oxy rorceuration =demercuration Comom mer 9 3) R-CH = CH12 ——> R-CH-CH3 T OW Reagents :- i) HgCone)s / THE/H2O ~ 8) NoRHy / 2 0® CNKE-ps) Ll DATE $4 iN) Biko xy mercurcation=dernertumatioy >R-CH-CHy oe ¢ Reagens:- ') Ha(0Ac)a / THE/ R-OH i) Monty (43.0% ™) Hydro boxation Oxidatior __ R-CHECAL R-CHE CHe > R- CHr.-CHi-OH Reagents:- i) oHe/ THE ii) Heo2} on® batts Pinta - Masicovnikev Idiborane “) for Aikeyne R-CSCH —> R=C—CH | i= ° mtr t- i 280 x eso ae a ee Se. ae —— =") More reactions of Alleanes Se ses 3 SM no, 5 enor! tio CHy + HNO, —~> CHeNor +Hi0 — | 3 CHa CHy + HNOg ——> CH3CH2 CHiN Oa aS = | CHgNoe + CH3CHr + CHa CHa CHs ; 2 =] mio aah Roe, = | 2) Sulphonation Only Higher members C6 onwards) ore sulphonate d . aw 2 R-30 +H RH+ H2SO4 ~8OrH 20 heating Lower members react with $94 jn ahaa DATE 9) R-cHs-0H Cie) R-co-R!' —> R-CH-Rr C285), ou Poicipee oriole MS - R-co-R' “= R-cH-R! 7 fe RR eer cca ea + p-t-on ———> R-cHa- 0H + H20 - R-c-x — > R-chi- 0H tH u A —o. +» R—-C~oe' pay R-Cy,-0OH + R'-o nV © (ee ce) La 2) Gouveault= Blanc reaction = See ° oO Sy CH.-OH ! -co-p! "=> g-cn-e@! C2° 1 On- ©) By veduction of Nityous acid on ___ Ailiphoti: primery amines: R=-NHr + HNO. —> R-DH +a + 20 *) Hydro x ylation Dom Hyd em eyladion aA Os 0 0 Os0u5 Heo Tost D. pees So Zn Erinow, Now. bn ow ; duo Coord dilate) iN) pnti= Hydrvoxylation Using peracids _ 50 ZS eres [ah Hie aa ~ 3R-x4 Hy, CKE CA Be T) ase We ate % % Fenzows rales Patho Px } { % u Hopy%e * RCHK it 8) RyeP with PCAs Cspr) io & 5 —— > R-CRIHAE POR; Reaction wit SOcts C& Pyridine) ROH 9064, = 20 coe DATE Soto i aa eae ——_ RAG4%5 = 0. + HEA Chlorosulphite etter yore € CAO 7 “a <7) Hc 2 ~a == 10). Sri reaction of Alcohols CNo Pyxidined R-OH + SOCAr2 — RERt SOPH HERT t ec H ce Noresulph( . S acieev it ( Rebention ) { NR FOE CNX PS) DATE &\ | Celioning tion | ") Pinacal -Pinacciont xeaarangernent —_e- 08 oo eae He CHg Cc Tk ae 2 CH Caan oH On Oo CH CPinacer) China colone) CRtid-catatysed elimination of Hr0 ) Plechanism ‘= CH cH | ! ee pea Sg CHy —C—C— CH \ 1 gH Ou. Ou 4, Conjugate acid of Pinacote ) €H3—6H in -H20 Ja, Senpoder) Nea \ OH intermediate CHa @__t CH3—-C—C—-tH, More Stable C os Hg —C—C- CH © Cy os CH CPinacelon) ~ pare __ 2% +o re (8-9-8 +i) \ n! \ SM 05-1) 2.5 Williamson's continuous etherificatior Sy pes _(denydradion of alconols}— Sant =" fant ors Gtneral:- DEE) 3 —=2 Z - Tgore?, CH2= CHa q-CHi- On Bore H280y, —" ; Teor?) CHg CHa=O- CHalHy +3) From Alllcenes ae r CCH32C = CHa fasoy. CH,—C—CH, ( emane ye (CH3),COEt © EtOH a t PAM 2h -¥ + A910 ——3 R-o~ Ry 2a DATE 3 #5) Thdustrial Method eee 7OH + HO-R “eoge? RiO“R + He #6] Miscetlaneous reaction R-OH + CH Ny —— > R-0-CHy + Na * mi ct with HY. Cha =O CH= CHy 5 CH CHa tr CH; + (CH3) 2 CH=0H (CH3),CH -Br e—__l. ov. cess + Less Stericatiy hindered parts farms > Xeon Lo, ee +More sttrcally hindered part Ferro. fitonplepeien SCA Ot, tipi Syl? ee E80 Sy! PE 5 9) sie CN¥t-p5) er! Ye Hudreperexide + _K'0-0-CH- eT Pratcyy Peroxide 4) es with acid Chiorides and ae Coe R-0O-R+t R- Cott 3 Be Ck ¥ R-CoOR Redgent = 7incr) Se > Sore. Sa ai Gish ceo ae 32 DATE _ 84 os 2) tit HeSOu iC EDs > RO-R+ Hisoy = {aEe8 es 2 sox? Ceonct:) 4 Bron + 8-0~ Hse nema Masia “2d | * R-O-R + H2804y —> 2R-0H Cdil-) 3)_ Puro -ovidationotiether oa 0 FO R-O-CH»,-R" isan se OS o4-4 5) Reaction with Carbon monsxide — R-0-R + C° ~Socatm R- Cook j2s-\g0°C 6) Rx" with Halogens “with Co or Bra 2 - (Hp t.-0- CHacts —> cu, cH O- CH, CH3 | Cea cin CHCA Cha it excess Ga ce Cz ck + CH CH2-0-CHa CHa ——*> (C2C4s),0 ‘ Perchlors die thy) her. Weehanism i= mee hindered © we gales cucu es ep aos Cur ® Toms into OH ce aa bbb bbaaeeeeae eae ae DATE &6 * Mechanisrn Cacidic)'- Mort substitued Coubon. p® Rach cn. R= were We o” Sy we f- pR—CH-CHe l | Kta—OH ¢ + av ether RR Mg RG Reactivity i- RoI? RBxr> RCR > RE RES No GR formation * Chemical reactions of GR ) Ber wite oodict Ft Z- + R-M1gX —> R-H + Hq — * K Z-~% + R-MghX' —72-R+ May! CNucteophillic substituton ) ZO Group having ~E effect: CNyt-p9) KOTG= RF RK NS RR Mg Xe J NV Renton inversion N=0, \seo ie) 1! ae R—-C- orlgx o> OF CO RcHo> Ar CHO * R-co-R > R-co—Ar 4) Su2Th 4) reaotion with acid halide = Q-crk Fe MgX —> g-cl& cr Son tea Th ing) eg! as Pole) Ce 0 R-oH + Ma COH)X Formation of ©) Reaction saan Wl ceva ues ne R-Migx + O=C=O > R= Cm ong x ° oe tee fod -t- € 3 eee) roe 0. Foxrroton Com Mater: Taal DATE 40 1) Reaction with @- ON ian R Boe cen 5 Qa =NMgx Tee fb pee R-c—-ny, G-—_ R-C=NH 1 OF DATE a1 "Reductions= y (Pg 48) Cexotherrnic) Se 6 iGed Pe CPs) i ss tal Catalyets CPq 352 yu rc» Rosernund’s catalyst v {Poisoned Hat Pay Baron C pq Cotelyst ) > Redes Ptegne te thine ~Resucer acid Han deto Aldehyde Sorat ors | Metai/ pro ten (acid) reduction *Metals give ¢ © to electrophilic aceagenit and form’ anion. “1 " if —the orinic source, ) Rink : pcg 52} precincts —__$___._ i... CN rtp) x R-o = R-cHo = R-CoOH ed DATE as | sen ‘con Reduction ey L 4 ae | # Orta: EWG t+ rer macuaugeeena Foe hay \pso- wou ®) Nv - 19. 47 Cyanide — It ening Ester ——> «1° Aiconot Froid Halide —s 1° Alcohoy iw : ue hon Reagents:- i) Sn RoidiGied Stannous Chloride 1) Aro TIATHy > R-CHaANHa (Amine) R-c=n Pate Complete TECUCtion \Wsncee/ Hee ii) Hr Rt che BS : , CMrt-p4) i DATE Sa 2 19) Clee [Link]"eace obi et Om ______ (Pg-50) g & LCHOW i) Lib2Hy CLAW) /etrer or THE Aldehude —> 1° Alcohol Ketone — 2" Blcoho | _Cavporylic acid SAM, 4* Alcohol Rad anny nee — excess, 1° Alcoho) Arid Cwioxj de => 1* Al\cono) Ester —3 1* Alcove, — 1° Ami Amide — = 1° Arnine Tsocuanide —* 2° firmime Nitve 9 1 yhonims) a7 (eee qu DATE NN atHu [erhe ie Aldenyde —> 1° Alcohol Ketone —— 2° Alcohol Btid Chloride —» 1° Aleohop W)_DT@AL-H] inert solvent Ester 3 1° Aleoho! + SE ee delays SR oa Se Cyanide —> Aldewnyde 1) Molt = \cisher wre duction (Pg-s0) NY Reduction wits Red Pand KT (Pg- 44) Aldehyde lA ketone 1 Allcaner S) Aaa & fred frmrg drt erter g fo Bee deae dad Pluminium isopropoxide ) DATE ay R-—<- R's CHz-CH- Che ° OH aoe Ma OH + CHy= Co CHg \ & *_Oxvidotion j25 Ee 1 herni i 1° ibn nO Cfo Allcunes) i Cr2 07 OM cHy 4 voy KMimnoy 1 & Tio {atv 07 Here t CHS eH; Tertiary Contyst za i) Bayer’s reagent E Coold, ditured, 1/4 Alicaline (CMIn Oy) A\icene — vitinal dio 6 Syn _add- A : of OH) —Bikune 3 dileectowe 7 SERRE DATE R-cR= CH — R-cook + R=CHi SCH-R —-» sage + CO. RaCecck e + Hro ih Citic +RCO00H — ewe +RCOOH A ° 1 ~eHz0 | Cant addition) + plore SulosHtised double bond weaets Faster: iY) DO zonolysis - for Alkenes:- cael > SC —C Cnet) oO. 70 Molozonide Canstabie) Nee LE, q4 DATE | attroy sc TiRUee Meee + or + = CCHa)28 /H20/ 0 oO tas ~~ es ae Reductive > 7 Beton <. H20o/Ha0r/ eb Me ae Co¥idat ve 1\ He any toKtaOa Oo oO ae el Teo aldehyde — is formed , itbecomes R-cooH * For A\ I= Rie =p! 2 5 nie ’ \ N — ood =¢t=¢— fe aod TLOvrane get eats C Nxt pgy = SBYDUPUPECEeeeeed qe DATE ~N ° ; C1:2-dicarbony)) =C—c— reach 2 Rete e! O-—o NI Ress PaO) | oxidative — ————> RCOOH + R'COOH * Fox teeminal Alkenec & Alkynes, R=-c=CH, —> CO. R-C=CH —> Cor DATE aa D CxO; inwater / H2 CrOy 2) kKeinoy /He 3) K2 Cr, O7 ([u® * Very.y- strong Oxidising agents 2- Kminou/ Hes pD weak OF Strong OF 1° pon > Aldehyde Carvvoxrylic acd 2' 2-0 > Ketone Ketone 3° g-0n > NA d Na wy: Strong OF ~Cu/hs SSS 4° R-OH Carboxylic and “Aldehyde ZR-OH Lea carboxylic acid Ketone apo bri cavboryric acid Denyarstg, V0) Oppenaur's oxida sign ________ -fecandory Alcohol co 4; obs Ketone + Gace 1 Common sp Tertouroride CheCoctter)2.) aaa Ketone. pate___ LO eas OH R-c-R + Acetone = _p-co-p' zone fare E RChaoW> Ro CHoh> R2COH CH y—-C— © RcHo> RcH.0H ay Cbg CNH3)2) RCHO—> RcooH Weak oxidising agent HCHO — COr ReHo+ TR => R-cooS + Ag) + NHs+Heo vit) With febling's solution in . i & Th Complerediwith tartrabe jon) Hoo ut © Rotor Co — + Ot —s Reo F Care be : ro" with Benzaldehyde: ) wlith Benedict ’s solution —Sadium citrate + NaoH+ NaHeose ry Chk cecal CHo + Cx” S Coo + Cy® Mion dn” ccmicad cos 10) a Red ppt: | Aree) | * RoHos Hg (4a + Heo ——— > _____ | RCOOH + 2H Harr c —» RCoOonWs+ a +2H qd ( Gres w)lalith Seniet's reagent. ag solute £ p-Rosalinine a0 = R Chloride decolori 8O2- NH~ Nye fo rer yout Cotertess a > Schitt's T Ceagenta) “reagent t = RTO RCooH + Pinks @NHL? Color- No ter Ge. | = Cyit) Cir ix rs JemtnOu or [Kale or More _on this later pare 10% * Oxidation of RCHO and RCOR' with idic \CMno x Ke ° AtHo + Co} —> Htoov RCHo + Co} —> RCOOH fs nolit high * Popott’s yule- During oxidation of ketones, a \ o ty, 2 CH COF GH. —— 3 2CH3C00H Cy €o= CHa CHL CHy > CH; Coo + [Link] 3 3 io io \ iO . ny CHg Cook CH3-uto — CooH BERR EUR Cree eg) DATE |o3 c=cH a — = = 7 3 — bury twill Pok be oxidised. *!) Oxidation with CeO. ver s, = 5 ) ee Carbony\ grove inte carbon 4! graue. FE ee kl ay TT 0. Qo CHy—c- PMA ocUee nN a) oO oO ¥0) Orvcida tion with Rromive water \ vr oO oxidising Agent * Oxidises Aldemnyde +o Ovid. Caroeoxylic. R-CHo ———5 R-coo aeaadaed Seah bbuaa (=) i } u i lou DATE some Al\icyne (2 diketone yp 2) Tones veogent +o ; : x0 Reactants: - Products == 1. R-OW R-cooH 2° R-OH Ro-CO-R! 4° ROW —> R-CO0H DP R-OW sp co- PR! Noi Cr207 + pyridine t HCL Allylic PR —> R-cHo Altylic 2RoH —> p-co-p qep-oH —> R-CHO 2*R-OH ——> R-CO-R' 6) Mno = reveal OLB - Unsaturated Aitylic 1°RoH — e-cno Allylic 2° ROH —> P-co-R'! 7) Peronides_and_perauids ———— | pilkene =u Coy 0’ ce —tenne =) 5ster.. | Soe on 8) Lend kebrancetate Pb Ectly Coo} 4 Q-c-k : Z , Cis-ding —> CHO] R-co-P'/ R-CooH DATE Qucet 1 QO lo lo Cis-diog ~s RCHO] Rcor'/ RCOOH T°p-oOWF — RCHO = R-OF 4 R-Co-R! 3"R-0H_ = Alkene F_Wacter Process Amount of Cues in orreence of oir pr o2. CHic CHa +H20 —> CH,—cHo + Pat =CH, +H20 — R- + Padcdr is veduced to Pd Chais reduced to CuCt) + Oxo- SPREE KR eee eae Bach siCHa Ss Rh Ca BICKRma Terminal ! CHS ' A\\cene R-CHi-CHe2-CHo * Etora reaction | Oxidation of Methy) Benzene CToluene) ond itr derivativer with Chromy) chlor 4 C Croc ae CH Cocron tarda Crortkr Cceasium) 3 7S CErara yx) = - pr acH, Minoan Pre oY Black C. Bier Co Hiei lS ia ope soins ees | Ben a . Benzene Burne ws igs Gren log DATE Beiolysi a 1) Eotere Mild acidic mediuen > dilHagoy (di RA | 1) Strong alicaline medium — 2q:NaoH | cou] a ; Me to Sen Ww Cosh yy Roof R! ——> p- rooms Boon OH H ME Leanjewitee SD ht he nln BAT eit —s aeggg a = | R-2-¥% ——> R-coon + HX ° 20 R= cHNW. —— > R-CooHt MH, i CN yt pay eae q pare _ 10% 5) Hydiotysic of cyanidec SATO R-c=N Sa ceee R-COOHW + NH; ‘) Trocyanider <= SHoe R-NEC ——> en + Hoook 1) Traines R-CH=NH —— R-cHOENH, *) Remiacetaissond acedale® — ae Gi-oL yo Re RioL a ea Ficetay eter op? SR ES rn 0 cont eee Ry oe mCMeraDE: OD han cane SR idee) lertomee easily. _ *Acetals | ketats ore stale and "| e ape He) ad Heh pot ce —3 7 OR Fe oH Wa Fie —a Cat ) Ethers 9) Ether: =m shes) a BOR rope. Deo or hevt me °c Deaia ge R-H Ma CoH). = 4 Decarnboxylaten an 4 effect: Th Aldehydes, —co- ,-Coom CHe ea Cory pour ty si ‘ Gn+r2) 5 matic + Gn qule > Anti- arvornatic Aromatic 7 Non- > Ant- Gremane A¥YOMVatic a Seep euaekeg dg (| ae Wt = OPN ay ——> ri) a Cd tcarboxy- 5) Grom Benzene diazoniucn CL By=picr© oe fej ae ced +N, tT CH3 2 Hye-C- OS BRATS 0 CUMEN & Geneene of es Hc -e- OTOH t yo” = 1 rome fOteT 0o + More ED i & r- -H>=Ph>-R ‘ oH oY oH ae he eo s on Hoo > Pie oie oy Crond_ electro. i= =—coow, ~S0,H, CMez , SiMe; 2) Nitratio: Oki ¢ ) it? n Prajor ORT aRVe oe “products On CAN Ne: Picxie ° aud oH ay DATE ae *Notei oH hal DN aos as 0 H20 oO Me Me : ae Size Ps s T>@r>ce gr C8tevic : o Hee Me oe DATE is 3) Sulphonatio S054 oe wise QAZE Cast) el majer \ HaSou Bed { S Cstavie) $ogH 4) ° O- C=cHy Ose tiga 3 e : A creel *)Prekectinn of =OH/=NHa 9VP yg u Ter Ce CHeCOCK Coase Toya ed aches Bae Weng) corer . 4 me acetate RR Majoy if Nao OM) aa Mayor it con COOH DATE {7 es sis of Aspirin. ation + Ce ee acco oH haat ra Soa nea 1» Bier = “Tiemann Tiemann xx" Ciormysatien) cH 2 ma Cmajer al || > Reet a oH On 3RafNi O Bie eA 12) Ot Otter Hy C—O | —Haott chs Sno (Py-12 Sane W Tect for Phenols ) Turns biue likens red ow oF am’ fpior= 6) ise id ; ion DATE 105 6 CeHsOH + FeCky —3 t Fe(ouHsde] Cviotet +) F SHS + BHC 3) Libermann's test 3) 2QNanor+ Hesoy — WWNOat NA2S%% vate 120 oe oan : we ‘DHalogenotivr Br CLewis acid) eee —Bc | 1 tC Z gyi ge= Fee Arrock of \ Be leatroeh haal © ape Sr By CBase) wil de eliminaon ne Ss + HBr + FeBry CN¥E 2g) SURE aa DATE @) ited bins) ot nips /) pee ae HaS0y tee 3044 HO- Now Cm T+ 30" + NOZ e— B2O7 NOv L> Sulphenic acidto inceeace NOz cone ° a ced + He +19) Nitrepenrzene Eriyroane ait} *).Ju\ phonation — 3* R30 + ROOy i —$—$§6— i oe @ aS, x Vv ® “AN —— aa + ae St ee eee Benrene cuignonic acid. SUB eeaee eae OATE eee 4) Ek f 7 ce CARTHY YN gy Gi aS hee “aed Ck ee ra®_ 1 6 Fy RECA REA 4+ CR o 4 yee + CR= ACR May rearrange dg ! ck Oo e ch=pe=ce for as \ Base | u | + Hor + ALCR, R ss DATE \2 x Doom t worst) wit m-directing Qroupt: ae pox ae + Phy eet Oana Then Proceed Hermally- S) xi afk Not Posnble by me Palen 5 a e- =x na ta) Friedel Cratas Acglan ee Clemmensen's Wolfe-Kishner reducy Dont with aad Cite Tearrangement ) Gee mort 1h module for theory e DATE rs £ottivating groups VOvthe-para divesting grpe Ge CT er Se chi 1, war | Willi ie + -O0- >-NHWi> - NHR > —-N@2 > - OH Cvery strong activatert ) 0 ° *" -OR> =NH-e-R> —O-C-R C8treng activates) + -2 > -Ay > -CHECHe C Activators ) pee —s ao are ortho. pare dices | ee > Ol ettete 8 53 se -—¥, -N=O , -CHX Te deacevator ss Cdeactvators ) a 7) Meta-directing axpc i Usualty EW Gr a + =CHO Boo “COOH =COOR TOK CN SO,H Qvbony! ‘ate * 4 G “TNO, -NRs9,-SRY,— CFs ee. ei opqdivector DATE « h ') Nitrosaton OH too HNO, He ae *)Diozocoupti oH OF (5 i ee — Tea Ce 8 tole) Sa Slightly garic N=N- PR P-Hydyoxg, NEN-OH CeXh 11-14) Strongly bac ae Grey Phen = nel xis o 6—Naphtret i <4 =a ° Color ys Aniline. SW J keduction of Nitrobinrens NOr Metat-acid Rye = TRTATH =a Fern z v 4 ob é —a Now aH pitas Ze me os No or QOS Now RHa /Hasse = +) Seeger -CO-NHx Wet: DATE * Retention * Dn tramoleculan 5 Seifoproduct ic Sie iel P al an ® mo ow a pl Oe WAK eee SE ° R-% — pe (al hee PAiphaticamine yy Cy, wy ReNHr €& af = aes Ne Aniline BUUEREEEeeeeeade 2) Mono- halogenation DATE (#) Sujphora tem 6 HH NHatHtSseq Js -e- NR HSH NH3 u a “ane SO3H Sulphanilic acid AH No to” with Friedel Craft: Alley \ation/ ° G Buty Nidv © Ntt=c=te 0 CH CCR —_— Cryso CR ed ALCe> BRR RR RRR RKRE eae 8) Oxidation 0 SAT 0 Beers OT \ lL Quinone E | ea wins 4 ____ NAHwz y A if z mS ae NH-C-NH Ch-e-k me 1 v Hg H-CH, "S@ ge ad i sar (er 4 MAL ° PhHSOrCk CeHs-S-NH-CoHs Hinsberg \ reeset =9; lo Na py — . oy 5 iin Niet AT e e 0. PHO EDC | weorety adic NoN-Ph Gominsiateecoa CYillow y pare _|9% Nye we No coupling. —_o@ ne NEnce? Bismrarte Bro wy i a Nonor+ fom Nofieuet a ale Cees ee Gy Cie ee Benzene Triatine pee EPA IH ia ERLTRL IL oo FBS ae a . On paswewee® oF NEN-PH tae ee O een NHv oH o: NH» ; ‘ h ic 7. = rcNeEc —B=NHa/ cHusenann @=NeC/ Pha Has Tage ? Ph-Nec? CL par) y ntorstorry CToxic/o ttensive) smelt Y_Hofmann Muctard oil xx R=Niz7 Ty C8z 2 R-S -Cocye PRENHT Wy Hg ae PR-N=coS Tsomiecganak (wwarrars on fren) j 3) ing RON - oe ——— EE Ce rt:ps) t SS Copt- 4b) 7 DATE _ iso ae Ponts At O— or agg eee : R-N ¥ re osgeo (alt) /solubie- oa . 0 =a Ne io Do RaNH ———5 RoW-S—Ph =a ee) 5 madi ; ee ET estate + Ban eae Nowe —4 C3") No pee: = | 4) NaNOrt Hoey Nanoy+ H280u Co-s*t> 3 = saniinins +_ penny Se eon + y+ Hip C4) : +_Ph-NHr aoe DP Roni mice = | Co-S°c) ‘ pb herktet a Pg-i2s COviinant Orange) a a. + Ri tH in pi atitece s gp Pett peg Q eases: ol Za Cviscour % Yellow oly [ayer) Now *_Checnical wxn's V) Hotagenation Now I Bra /fe _f | pars 7) Nitra tion Lo] 0 veachen <> Pith Se LEC Acylation Nor Gaehericis No rean” ree BEAT NO MH 2 1 Pa He [Ni SSS ORO LO Basici med aaane> NA oe A 7 x3 PR-N=N—Ph + PHO DATE ie6 a WERTNOOW ST BR-NH -NH-Ph es GRAMS ATSC HT CHydrato benzene) GH tO [= somes [0] 0 aE med- oe Ht Ott ee o & ghsrowtedih Wreaicran gem ent 3 a mela! . ee ileen— u NO NH -0H Block reed =a =a —2 = —a —s =| a a Za 2 a nts en NENRO Me fe Sj SS or sha ROT yen 7 Coor) ———$———_ _ _ v ter in @n= cre CA ea : aos NOW sie, LOY sg @NENCA ae Fal DATE empat as 3) Galz- Shiemann >cx” SFIS PRN Eperu oe BF2 + No4+ { eee aNo, Cu eo Na + Nabey + Ha + Negru + CoHsnon 4) Gombery rx SU Sa Naorym Las o> 5 py Gs ey OY Cau powder + CH3 COOH BERR Eee ae DATE @ yence® y 1 Sacinan i +Hi0 ls 4) ONE Nee = Hao Ol Sa Je @N=ENAe L 0 SS Ph-NH-HHa- Hee Bricuceee yg i Zn/Her ’ ae To PRE NH NH Ph-NH2+ NH © Zope ny ONENcA9 ESOF> 5 = Aro LO oy Ph-NH-NAa pare Wa -Ccools A Idehydec _letones &, 10. ® re ') ‘ ; tp 't) R-CH2-OH “ma F- CHO C1* R-OH) : PCC , - -2)>. —— Cae Wy 2 ee z = @ & RK OF ° T2* pon) 2) Dry distation of Catciues salts = aes IN j Urals aHen . ” r DATE & 42 ) 8) Wacke *s process UCSC Paha, > CHa He ne Ethenk @) _R-cH= CH, + Pdce, ——9 R= C~ CH Other Alkene i a n 40 Fac o HeTeat Rae ate Ratog R=cHo ‘) Ry OTOnalysit CPa=aGye 5 FETE) eEs 4 Eel IE NY Wudration of Alleyn C Pq - 53 4 pate 149 a be As ot eee 6 i n fp . x Oo° 6 rine Tr 2R-cooH =e R-C-R + Cor Cvap-) ies P07 PF + Ph-CH3 CO ——. Ph-cHo “2 Blicyine ny drowysicot geen, dinalider OH — maaan STO RocHtky > R-CH — "5 R-cHo 1 CR = OW “a 9° a ae ee ae ae \ \ Ck on 2 Ro Reagents: KCN, */Hitow it) Noch, H+/Hei04 WW) HON, dit-Bace- ey — R=e— 08 ss 2 lo > i Ky SRB E EE Ree i g f Ah DATE uc 4) Dddition of NahSo, R-cHo + Naso, — > Q-CH—-OH \ Sostte Cerystaliine J Nee R-cHo =H R-CH—ou Ceurcy S ow R-cHo == R-CH-on Ck-> ki) An mares ) ©) Bddition of Alcon] addition of fAlcoho Oas Wts:- 1 * NY Glues or Polyots i) Q-@H or CH2-3 H® (Thicalcone) arerere, EN —____ = j DATE gaan RE seas not A dry Hed a ET 2 RT dil Reto Heo® — * Used to pretect —CHO group - > ~ R-tHo TEEN geen (Prceral) = > OP ita utd Ae Me vdaniven eid. c-OeWiN-t oy CINE 7 -a t = | ete +H20 =| “Yee Lec notes for Some preps. = Zag Pana NW=e-NHe localised Cserni-cavbaride) ‘ YeALow cao ¥Wen-nH-O Nor orange Pv Soe ae p O2Nn C2s4- dinitwn pheng! ) t a N-NH Xo » Now Orn *Ncz Be Le eae tie 4 Hank His ah _(Schit€’s base) i - wera. ow foe + ee att AAO 6 PRL re Conzamine) CAs or SOCR, ovede. ns)

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