| unt & WoLECULAR REARRAN QENENTS eee o_~-[T-_T__[T'[_[/[''\" SS AL PIWACoL- PINAcoLone REARRANGE NENT | “The acid catolyred neamemgjement ob La-diolA, ance Gnvented —to @abvoy\ Compounds wth elemmodion ob Wwoilm rrolecsle TA, lunown oa PINACL- PINACoLONE Reasons emnent= gh OW WSou\4 = f R-cG—c-R > RG —o-R \ \ ho & BR 4.2. diol _ pound ee W2-dLol Be CoMted = Prrocole & Conoony) Compornd GH CoMed Pinawlone, « ® R~c—oOh @ a 1 > Ro Om “eo RSQ are) a- C~oh \ cana \ } R-c TOW Rec oh ghibt R il \ aR B : | eee ee \ si R-c-O-H Re es @ PWACALONE { t APeUcationg ' rele = 5 | CMs Cy tisou| yt ri we | o Oy —63— o—cy > My “S —co—Chy, | dn os ) on9 Gis-g — cw Wy 1 1 on ow re M ans | NS cH, e v H-o — SH—O Mwy — OG \ \ 1 = GMs @ Ms 4 oS chy co — Ch oo eee feo) A ou (OW u 2 WAGNER ~NEERLIN REARRANGEMENT Reackiona, Wrelving “the Charge wa the Gabon Svakon trragh “tre neamvugumest othe Gnbootion tipumediotr one noun on WAGNER —HEERWIN Rearrampements Reackion The veannampemant trrwertre ley Stable Crbo Calion, Ea move Stable Combo colon co lo ie) as hy —C A-OK + yy -C = CW CH & CH SC -CH, CH \ w bay a-nety\2Bulane 2 Hebry | Neo pent alcoho! oo = eu mchesiim | rN ce Os © a X oar —ch,-OH —— chy —¢ — CR OND, J 2 Oy oe co @ ce -~d— ow \arets) cre-¢ oh CH \ * SE? : hs Ns P combo colton 3° Caxy'eo ation> cM —¢ = CHO cWy— Cc cH. — CMs 1s 3 Gait ducte ; os wyfen coasugolion . Os c-ChN Ms aus AgeLcATONS aS o x Agra. ae Cue So ee ee > TS cycropents! Eode oy clahescome nit gyctsworome ss @ Boe won, fe wm eos TT gore Crgy\ ontoingt Omlne, cacte ots' gyctonctome| Conblro\ © ch a eh roe Heme Sy pho SON-“PH c Ph * Ressrompacnonti “to Eecboon debra: rtbeogen 3 HoERHANY REARBANGENENT REACT The Reaclion trvelweg “tre Conver Alon al om Ornidhe trite & Prim omtne. Cth ome Conlon lerk, \ ley “bre ackion ck A\vadime hyPohodide CNook + Br_) The ra Reaction LA, eran, 8, Vobbramn Reaoromgannents | R SowR & Hn, +B Aide, a may be obs photic. 4 uNack —9 2 Ny, + TNOBy + Na Cy + Ww arming ctw gy CK onomoatic oh 4 a Not OF mechamiAy Wook + BY, — nooBr +BY 3 ° + g ae . ah ak owe TO, pd nu-By OF, pt -N—By —NaoK ee ag -3f ag a—w. ann : oh. w ee ea i) pN=cH0 co 4 co eG wo, a-n-cr8 ann C8, o-n AROLICATION'S, WooW N O ce—w-b a Siar ie BY o te noch GMs — NUL BL Donetde © Congc-on Bon 2 Wn —o -N, UREA @ cot © N picoTINAn IDE Se reo pent) Orenine. NooByY = Wh —NY_ sy angen, BAN «a me ba Frame Paria' cai ° © = a Nao, CoN, moons ee / aA Scooh PY Oe ANTHRANILEC AC\O Ptrolimide % BECKMANN REARRANGENENT The acid catalysed Grveraion aly keboximes sho N- Subalibcted omides LA, krounag Beclemonn Reconramg umemte Reackion The neackion (A, Cotalysed ky acidic Reageak Sacha W509. WsPOq. (PAS. Py Phaaphoc add E Bertune Serrrogys| choice : So, Taner! ee oe Ve - chsted ovmi ero xin N-Subats ide. nechomiArn ( » ‘ we 7 . me * x F 4, Bem Nea n-OW, CaN; oo eos =N-O1 Tinea 2 we ® \ @ Sti as R-c=N-R wa rb eo) Se och a \ wo Vie male a-fon-e! C co =N-R —_ = oan Be 3 — ad _wer? STLON AgeascrTans . n -OK: Clone iin, Sut cw —6 —NU NS S22 nonctyy\) actomideOo ws g WSoq HyC-¢ —NK- GHS ire =N-OK > N- Ee acetamide ° N-O ie e » WuN-O8 ) W504 Nk oT ; CycloWexamane Cap RoLAcTUN ® Oe on Wasou\ vt can > 1) a\-wo Phun cyomide SB. cuRTWR REACTION he necomangymneRE trveWwe tre decompoaibion ok ory \onida 1% am trevte Severs Conorcheven, Bemleme) ty Gently, het: “bho Laoqjomate R-Co -Na, = RQaN Te=G 4M ah eR veackion A Cormicd oak tn alcoholic CD eda | che Usqyomide lurtrer recat: 10 OeuewA born dabbewrb~ dewNotiver qt \ \ w RI-oK 5 Emm =e HO URETHARE Q-N=C=0 WoK ; R-N Ww a o : Y \ ae, Pec NAP SuvAbtatd. weaMECHANISH TT ve Qk @ 9 REN &5 ph nsNen o> ak 9S. oN. od a >> R- sue, ai a pon v \ . eS_Nt CG R-N=C=0 > BNW —c-o R ARRUCATIONS a Gh w 6 Oe — at ° @ cu, —b-Ns 9 Wo ° Glew Bons ALC : G5 - OA, “NA Was ©) WAN NHL con, &&% CoGhs weacolo y- ON “A Wto LE wGs La aw Eki) omi Rote, Macs 2 ODeg tee (P- Anigidine WwoL, © > AsGMe gic Na, ——? RCM, OH Recew Ee SO ashe oxtackon ReCOoM H Rearyanginments “ee elechron dibicsemts AB ey Bim 6 BABYER - WIGER REARRANQENENT the Reaction PrvoWeg TEhe oxiaobion ob veelong, doo Rat by the beck wtth Procida, Sechag Penacebic ootad 1 Pe\Berrbvic acid oTy\ Fivovo frrocdic och UA wnoumag Bacyer-ViNiger Reamamg etatom oat ° 7 Ww a RBc-o-®8 a7 RSC —o°R 8 BT eal tered niece Elechron Releaging BFeuPA wrtre vatore « & crchran uit drawing, BvoaPA try Prrocica, rigrotion, Al vey VOOR PS : A sez 27 7 CS Gi ory, roaivy\ Gs ae 7 oy) wy Pamtayy > PTY) 7 Prams) > P-chovo APQUCETONS, Prong ® Preporokion ob cata CFs ah iu D eMg —C 0 -GtS o Gis ae oy g cry -C— cre), Fa OOH oy, ne (oa) 3\ GB Peparotion ols omby did oo > CH a) Boh, ® Prepanolion ob Laclernea, ° % cs COM > — Cy cho ferbornre oy CHGS co 5 cyclo Wacomens. oe emp bo RSH eo omen REARRANGENENT TEEACTIONS ane: 6 NEGER REARRANAENENT REACTION ee Conn {AG of-ornind \eekoxime. rosy tin on Vetoes, trctne § Preacne ob pase Ta NONE, NeEBERL Recoramgements Reoction ne oO \ ans \ y \ Rech — Cc pone) (te Ce —c-R y w\wo wn -ST5 mreskantar y Gksd 9 \ R-ay,—-C TB 5 RHC —c-R \ i \ ae) N-sTS N-oTS, 2 mreamMigN y c Ro—cw—c-R WO 93 eG ~ hy 2, R-chH— ce! \ MEN N ~ 7 ao Ran -B AD\RINE " ) ~1 Cas- peTowne se\rroraneide ) APPLICATIONS pee < a! io i Gack o-oo s @ ph-a oS ee : PR-ohe Pe rerack Py\ ors N-OW Se \ ‘ uv oe ae 2 ee Phecw —o Ph Psvidine ote pya\oIine ey . [pra é oP 2 oy Ee NBR we ® 2 fo Soh me Meda Ph (al, a —rsc\ Puvidors eer iABA ARAN 8499944494500999 ! COBH ORAAREFAABRAAD we@ = St ne Te reer acs hover ment de hen te nn nen SL. AROMATIC ELECTROPWILIG SUBSTETUTION 4 wre % SumsTrTUTon REACTOR Te AAAS Reackona, usnich, invelwea the replacements de om stom Cm gre? By omathen chow Cor) GYOXP ot “the Some, Conlam ts tre lemded one called gute titation Reactiong the Subalitshion Reackiona, bakes Plece ort, abiphobic ox wel a4 onamclic Com Pom da, Ss AROMATIC ELECTROPHIUC SuwstyruTions REACTIONS Eleckrortalic. onomotic Subattitiion A On peaction tr which ow ahom LA abbached Ee om coommadic Syxburn Chyaragen) La, merlece® 5) amelectio- | Pele The Oromatic Systum Comb ainaL vagh W-cletbon | demathy ehh Yeorts thy elertomale bo tem guoabldaa ‘Proaech ogo € subatititid Berber Necro Pike Subatittion de eaateas or, & ARENILON con Coy ARonanc = SS ae pare pECHANISM enh Centtime LA FONT, Fo comygatia. double bora berovex Oa On electron vey Syitiny Ag ve erbama STE ovoilatsie —to bom news bendy these elections, nreod\ywith Elechorhile Thom SP canbow Chomgea ko 99 SP? canton. C empencyy leas cb onomatiacty ) So stabilttyy ob Bevkure decveages . Fmolly 90804 Wydrogem TAL Eliminate ag, Probin tram Geckeme 7 ek, Regonamce, erensy & shabby ° S HECHANISH ask TVelves hve sE.PAL G : e Seep Foomation ch crecbioPKle D ® Blechophile, ona, Semnatia toy the Spon tomeoug D darrocobior ol meet Cov) by c@bly zed decomporilion ef (oN Sa ” eon’ => CO 4 ne Ste Us a Electrophile ctobac kins) meta, step Elechophile apprecch oT he Onomokic nm uncegees tlectiomenc Shbedk ott the neauit one Conte chom geti svely chaged amc othe Beh, Nely changed TH Elezbo Pile othacka, On oregitine, Cantoom ve\tirg wth ovmnotion ob om Wlinmediot TA noun az, Conteniva tan Con Aremiun Ron. Cov) 7 - Comprese - Gr {e323 Mo, me digigteate: = oo ed skaiiZed, by Ragnonce. me RRR MAMA KHRASRV|YSeA*SASSESBESSTSTSBS' f "739" 4490 U9 99 9DVRVORE SEP Foymalion ob Product 2 From “the Place obr attoclangy, ereebopkile. hydoagen U4, Elonmatid. oa Proton “He Bemteme Ring Bek Reaenomce, & stobiltby o> a The Gove mechomism tA Called Ayemium tan re chami Arn AC ELECTRO PHING Sopst pruTion: REACTUN aa a ——~ om AROTIAT ~~ QO NMRATION Bertone Vente ott nitnaken mode, Cl tnvokioo che Conc Woy ¥ Conc W204) ot Goce bo trove, Nittic Berteme Wor WaSoq_ & Wo -No2 el ae + HO Goce es nittne Gerteme MechomiAm * pembeai ay Three SpA, =k mvelweg gkep - Formotion ob ektoprhile EER a oe a ® 2 2 W504, ~ MNO, —— ro * HOO ~ 2hSoq Atkoc ob crecborhie shrth Electro phile) ottoc ka, on Bevteme nitkonium tor c te bern Conveaniven Ton Cov) Onumium ion NO. po: ‘, u Me @Q * bs +r — T os = ‘@Stepaw - aaa oe Product Eimmalion ob by dcape clom ag a Proton from anodumiow coget “Yeamamnce energy & ghobility “HO Nor, No, eo > ae com Noy Nor _1* \ @ ——a T+ 5 @ Anwaren Promalic ComPomd 4 Com be Gmnverted teho OSomolic Promany ominea by ectectomemt ath, hyrotic ada tre Pregnte ob HaSog Core W504 Sh ee = dew Techamtam > shodat Fermebion Loe ekebophile reed ict WS0q — ® 4 H504, GeO) vw ite ew ae —» WN-NEN — NHL std) - Atbeock ob Etezbeo Pe, aA — vr es NRE me WOME [| eee} wy S Ss Ma oe ° a a o a « g 2 T o 0 | © @ 9 ® ® peceeceeococe ss eosasessseee ALARA Sci nhl est nds en bebeese binder wimntdasis okeoecbea MA, } SEP Wy V Formation ob Preduct = | OY 2 wh. j @ cs ) al CANINE) i —W S04 a } © Weep “Teran REACT | aia, Reackon Cmaigh tre Crvergion ol Phendg Wit Prenalic oldelycdea bY tyeotment with | Vat & Chiovobovre LA, Colle RIENER STNEMATS REACTION EX Phencla react with Choverboven tothe Pregame. ob Sage bo bam Salicaldey de OY tho -FSowxs) Benitardehy de, NWECKANIA Stags Rexmolion ab archive Galbime. Cexctiomle) 9 A eA 2 0 oc —c\ << =<. pote : sc. ¥ 2 Garey 77%. c\ \ cy dxchovo Con bene stexGo + Famobion ols Phimoxide. tov On we oF he stupid) = Fagmalion ob Subatiictea otdeny deg FS a ° oe \ 1 yi UN o%on on-Ole a video (pt 5 see COOH HOOREFR AAA ARAR ANB AAA AB 95D 99944998999909 ; SAPPUCATION se The Reackion Cam ber applied Some Vetrrocycle ComPorty Two phone, Povvole. & Strole € 7 Meds | to! S i) me » |. Me Woh %. THIOPRENE chc\y, \ iM Yow HW pyrrole 2) ” cMcly | Wot —> ENDOULE \ M7 CHO w we ® @) vusneen- wre neacTion Acetic anomalic ComPomds, eect oath, : One Cornet) Formamide) & Proaphowa, %O chiovide. to ave oldebytey SBR So THA, Reaclion UA, erowny ag NALS EIER — HAAG REACTION | 2S x ergy NCH oo il OND Ww Pols. yco och — ca M geneknony ot neby\ SE dy AW (SoLE, FORM AMIDE seoeoecocecnceooeoeoceoc se f5550%enemas OOOO ORO AAARAR ABA AAR AAR ABR ANAAAIN9N9N9N999099999 CMU A a RR A A WW meow ahd ac Lee Ua 4 nemAnen step ‘= 9 RR a 4 5 a a Oy \e ae N=c—o-F op IC Gayt=t oh (spn cz0 7a ae iG deer a cl ? 4 aay _ S —. ae = Clie (sw = eqgrh- — CS i Gea <3} Cw N-oH-C! Caloe cation sip WaCo oChy © C if — “ork e =nwx) — aC ‘ oa le \\ ae eH Nee) a oo? Ochs Waco oh baste) > Ss — Ch SiG) oe EN Cty) \ ic S Wc Ochs Ci Zi ot Cro Tu APPLYCATIONS, ce © W oR) sean wn TECHANIAN ~ 7 AB yic= NH @ weeen xencl —, 4 x @ S WY yee SNH 4 Ally —> V-C=ENY 4 AICIE ) a x y @ Ga) oe tah © or > =NY e —™ wo eiiee a > TF ¥ wo Yeo E=0 > A Vp) Ee Continas Z ApPUcATIONS pide oan i ONGEAN on a . Als ey By vee SS Oy othe. Pregemce. seeceocogeeoesoe Ses ascepat a ie i a nna et eR 0006666 C000 OF ORF AAO DBA TAN 7999999909009 S % ORENTATION cory Reachvity cb guboalilatid Bentene The SoL Wy dregen atoms, ob Bevbere nucleog 3) Ore idembiaad hence He BEaP Cx) TAL onbroducecd tS wh iA otek, Ae Berdone UCLA MY ome Prods On the they hand Shon a Second SHAY ctr OP 4 imbroduced HA mmo Quralbated Acuralive. “yr ee TLaomenc At SubAlilatd poaucly x * ty \ i ww Ww ce! mimo Subslitulia avtho y phi dowvatre Pana a& Subsbbtid deonatve “The Reactivity cbr weno Subalitetid Bentene Cov] “tre orientation ob Trcoming Subabtaent CES) dafindy om fore native cls Subalibiert abvecdy Prone os the Ring) %& The Subslitiest actos Heckionvelaging SvOAP So ik veleages electra —bowandy tne Bentime Ring | ene Feltowiny) Rexonamce, stactaveg one obtained, Car R ok > °. \ co | Boy ioe a ee te Erte above ReQmMamce shactives electron demacty Meveageg Ccanvamion) tn ortho &fona Patongee —_ THA, thege. PoAthiona odtocledd by Mmtoming Electiophile So thege ane algo ated 4 oFtHO, Pra dincclivyy QrouPZ oxtho « Por ddeclirg BroaPA, —nM, MR, ON —o-ths ,—CHy sbony ockvabrss ae ae (“on oclivabns —ai caeeriey activabrs, — CH AN ofthe «Pon dinectng QreaPA, Orme alse Coed ox Rims ockiverbong Qwapa . ex el oF pS area a & |p ot ya oe Elechon withdrawing ib othack the RESO NA x bce Subattbeat ack oa Souk Peau on Berteme RivG,. arectron A, om “the Berdteme Ring. Sethe Tettowing] Reagnamce- suction one. “ cltbaine o-(cr- dys 3 eecececes ° S é ©8C666CSF6S 605659595905 5598 29390908eo qo ~ — 45 OOO MODOO NARADA ATA AANA IIA I45 55509 : 99929908 Pe Naa a MR ll hh Sted naman 6 “Eh the above. Resonance sbuctioves .Conloe arlion is bormed at orbwo & Fora postions celecbon damaits, Aacveoey ) THA, Hho clechopmie ectin Wto tne meta Poailion Creabvery, electuen Rich peailion) So there onc alo called a4 amet. Coy Ring Beaclivating SPA atrclog BrouPA, Nebo ddeecling SrOOPAL : a a = i 7 Q —NoL, ~So'. -can, tn, _dLew;,-& -oH, —C-OR, akong deacbvaling, SWPA — Nor: Sp. - CEN ~~ ~~ — wears daaclvaling souPd % = omentarion oF wTTRO — ° ites ~_—_ \ ii eX e. 0 a 5 ic qth RESONANCE STRLTTURES w\e \ 4 ex l- ra Hy ow * ower) 1 W035 W564 Rt se peer Oe © tf + Bartene —Tolewne, o niko how, —rtene — POrE-NbLo Pleune ° No. tte oe 5 weal cusctaicly \ WrS04, 4 Ee Buritene. niboBumtene. am-witiommleone |® ALWPHATIC ELECTROPHILIC SeBSTITUTION REACTIONS —__ pee aes ER a Chumitad yeaction. “ene akon Cov) Sreup C4 Veplaced bY OT electiophile Ty roun ay Eleckro plaice gubai tation Reaction Bkectropilic subalitition Reacting one Omargova, ko pucieos Paice Subalitrliion Reacliong Electropulic Subatila lion reaction R Ore Proceed Envoy fyvenation ob Bakamion OY wtbwnediate a Electrophilic gubalita ion Reccliona Ore clayibicd © Poco even HEPA, © se ReocborAa, @® ser Reacliona, Co Set ReackmA, se) REACTION a ~~ sey meams, Uni moleculorr Beckrorhlic Saba ltiben Reackon- rE Sem ilo TEP sw pay 428 —R-t + ~ Mechamiarn'= ack~invelveg “THO sepa stpts - Formalin ab Canbamion AY foie oe oS — @ e wd + RB sere ALock ob Peto PRL © eon — R-*E © 9 » oO a eooecocecoseececesees: 00000909999 - 99999999 . rr O90 ° ARAARROABAABRAAAAASAD , 9999 29° ° rome ne QoQ @) 4- cy 5 EMS @Q xe Reacken * Se mom, Bimelewtor Elecbrorhhe Sunalsts kon Jon be Sn& Raachon, Reacion ZV Sew = SN Reaction the momen mucleopmle |! ae “eo romn UrNenAion. Cockigwelion } othock tv back Si Bhde OF SE Reaclion wey otkacs bmowt Cov oy well og “mv oA Conky > ae Dp a Y ration eleztror le frown velimlion the oncoming y woo Sde —to Out OX! lion NA @ se reaclon set meomA Intr molecnlon e\ Reackion =n A Reaction We obAoWed tre bemnotion Ch Four wrembeneds Cg.che rramaiion Stab. % corAoved ; 3-4 E-y —> Sy + 2X catia PRC subalitationre Rae Ne chamiam nN fa) ee + E-™ See BY = % \ ea. peau ae Four ane ove cyclic renal bon state callie co ea anion ne Oat Ardebwsen Cor) Vetones, Comtscininns) Cis Grou yeack wtth wologena rcthe Presence ob Boge ko Save halotsorm X oe NAX + SAO Ms Soy 43% +4 NaOW 2 CX, % 3B) us Wodobom —& \ AM -C-NG c y > ©656$6059999999090539090399000 i \ pechamiam - : . iO ow es ay oy Co Se co 2 \ x= Y e x o v eu, —c-h eo \ x 0 @® tow Ya, Nook (aaa A ook ma —c—w ~ 7 ha ae one re Gate rac cov NOX — Nox Cn 9 Qo Yo @) wie f 8 — x) oy CX, ¥H-G-0 \ ov yn % Mini CAxs + y-$ -ona Baboan eeceoceoeeceoseoescersA949 4494944499909099T ODOC FFA DAFF AAFAARAAAB AAAS APPLICATIONS 3 a ee CBs 2 HOB ATH *3N By » Sw 4 NOOK oO X Mona + 34,0 43NAT @ ay-h-ory BTL CHT, * OBS aS Uroow 3m, cw, * Gls Sona + WH 43NOE ee ° @® qus-&-%s Nao * ends + oe 25 Ci Oa — ESN *~ 3 © Sy ene CMs a erm ae sy.0 ¥ DRO WALLER — BAER REACT ICN ch vetoes trrto. Hyde mee S <\ N oF oS iE veto. mide Onnidke. AVNER inctshe Preaunce 0 Wee Sod ourmi de {_@ oa \ i akg xr 7 TR ERE wyoro Conor eho AM ~ re Sa nak C4 \ Senn. +R ae a \ Nw 4 toe are is Rr Nh Proton 1 2 —_ Ans Q-6 —D* THEM! APPLCATONS i NaNhe [2 .. | Ace PREWNEbm chinh mean bt ae yeeers | ® &rs -¢ Gus | Ge ize PHENO E ° \ © Cy cy — © NS } omy o @ M3 Q | Cwg-cH —C- CHa, — OE, Nant 5 aN x Gus NaNhr yor CHD Non ne CHa —Che Soh Owe -cH s 2 _t) Ne o cm Bn + BS 70S+9 ecoogg00c ae eee reeecooeeoescoe see S8essrsstunite cu A ne NAME REACTIONS ~ A PERN REACTION the condemsalion between adromealic ote de & aripholic ocidLomby dude whe Prama by Sei Cord Potasaiun Salt cb-tre acid Cowes Pordingsy Ter the omlydoide. we give GP mSatayvoted GEA Clty CooNa 5 Gis -cHe CH-COOK VW -\80 Hs -CHo alors wo) 9 Gemordelyde Acc Cina 1G, OA Cat. um satrrotidodd) Necrariaigen *- . o.@ ch Cis Coo Na => cHycoo + NO ete fe i. 3 a So x W Ga cv 8-0 S-oy + Ow cD 5 Sy -G 0-6 * Hy COOK, no Combam an Cu g R 2 ° i ° (i) Gg —G— (CH, —G-0 ~C-CHs _, . v i ‘S$ Gits-G—cHs—C -O —G-CHy w Cg Coo! a" v X ‘ 1 V 5 eis oon 8 — OHS ees 4 A —hL0 s °° GMs cued 2c W209 Gig CH = CH—Cooh, & C4, COOK A ATELICATIONS © Preponetion ob ecp-rsstratid octdy CM GoNQ Cus, CoWs - CHO chs, CHa,Co \ cMs (ous OMa.CO7),0 2. QWg-Cy= b— cook ok Met] Commnarnlc aad@ Sgreeria, ob Coumasin co ter. Aqo , AcoNa tol s oy A 5 ~ 7 Lo \ M20 * “ OH Coo SoOr GA GARYAL vero. Cournostin @ syatheaia, ob cance styr| cno Aap , ACONG Wn oy Fesoq a) em, ST et. Tee 2 Redaclion op 4 No, COM — Pedncl 0 -Nibyo Bemaldaryde w= cH wel & rol y > Wwero 9 = how er . on conse Sty \ @ Syntreata, ob Fig! acy ocd To Cree \ ou che cn ~ Cool, of CHO Cy Conia, A Furom droidalyeoQLCANNIZEARO REACTION 2 RANNIEE ARO RELCTIO Base, aromatic Inthe Preagance ob shuns, Coon ax protic aden dea, ast oot, X-ray’, undengo sak-cxidcbier veduclion fe dia rroporlnobion veadlion sTHRA TA, Wonca OA, Comic tono Reaction ur DL Gag CHO -F Nook 25 Gitg-C¥-OH + Celtg-COOND Benbatddnyde Beaty) alcohol Sodium, Tanto % Oo W-c-H ~* Nook AS cwy-0H YH COONS Formaldunyde Teta) alcoho | Soaiven ornate, MechamiAyn > Kacy <2 No + OK o en ow \ \ Gis =o 9 GMs -G—OM in j ¥ ° OS} a. 8 eg 4 Gas —-G-O* Gis GAs CoONG APPLICATIONS | - Gy Crossed CARWIZEARS REACTION SS pera ane dy the mask tnPortont apeticotion wy he COAACA, Comnttiono veackion between Frrmaldabyde caeEL athe aldelyde having, Any dinate’ ° a a weno +node cHow \ Gray ca — 678 > Gx re a Aide\ Con” cHo NOOK AMCHO cAOW Ea ew aH CooNa, CroAAed @rnEEano Gere 2 20K Yeack on : subabituled, bi regime Sy! wy g a MMe + NOM amon chy-ch~ 8-8 My -C — cron AucolL CondEN Nn SATION cates emis Le 2 onoh ae ComAred, Dorr EEO evs—cmomo Readion enon Lan aigdnagy rebyt Etrore. w) “ x 7 Brcwo + Naot a os ad ——_ wo inc- c a ALool Conoen SAnON cue waco oot Cy-0" ao tho : > WCOONG Corded, Dmnvieoro AW.C= GCMs \ Peockion bao Tes vetiyy oy ackiome. © crave. melewlon ComntZBono Reaction Cfaldeyyae, Gt — vate oldaby ier Urdinge wha | smolecvian Commitono Praclion i sry Voxi0u. A Product | | | pe| 2 98 & i 2 Gus —6 — F~On * dang ST Premy} Byyorc00 9 08 9 rbawalecwlon 7. oe Cos — Sok > 4 Prckin TO Aber ee om 9 @ yg_ gn moo 5 yd do Na wrt ¥ Gyy @ © syghvenca ob Vesieuar tara ob auger Kasia ; Coon Oy Re yeoy is : Cook Coosa Cooy Ary orobicosid Sodiuren Gyo. So DB. DIELG ALDER, REACTION are. neackion tave\ve™ Dre. \a-cddshion cb omalme on AdduEt> ob Btx- to a Comugatid dime boom a colted be tember Ring, The double loan Compound emopwle . The nection Ux titiatid rormely om Lewis acid catalyab . with Cor withoab the Ure ob Swenk, [ + \ (1g G ‘ ‘ y BSc + ed — 3 ee f 4 1.3- Bute oe : » ase Se —— a Techamin [I Gy Polen’ Pan a a, i) —T) G1 Fyeevadical gx - C—O Wy concent aoe Appircation & ~~ © ockmmmtnation a conbiguvalion my ALL — woo, Coo 1.3-Gubodi [ cook = Coo osikCoH Sy se — G7 coon \3-Bubadiene eae CoM 4 Coron) ee @ — Rynbreara, obs eeoe G4 (uO Fe Coe © synch 4 renee | 8 ' y cory 2% woyns BY Kost 45 ye AY © ¥y0 Dropreme — ned NY oe Veto yon b LT * a A-TERPINEOL @ Sypbreaia, ob comaphene “ Severo SEPA ——— cwo S vw »>1w Cycrofemtadieme Adraldalyde. Ci ComPhene4 REFORIWTSHY REACTION 7 on Conbonsy\ mPponda, near catty ot promotes fig exernce- by “Tae om “Eine metal & beltoued bys Trome Py entary Tha, reaclion Wyerolyata “Ee ave B- Hyder TA lenoun, Oa Re bovmorbayy Reaction x Sas eos Rodua! 4 By- cu -O0EE Ouimana Sve otcus te ) etme X-BYomG ea, © bes me B-wydrwny extn Dechomtays 8 | By~ cH, ~CooGMS — oe Cae eo | Ether | 6 Q-anoy | ews bok } cm = S— amo EL ey —EnBy Q-2nBY Pont | ey Ene 0 : 2 = CH cooet 5 RHE cy — Eo GNs y } on ep) vst Roe —On— do GMs i a A ‘ & X | ° : ag ow 5-0 GMs — Ro =cn—t-9 GhS —Wo ® nt APPL cations, oa © Lengrteheming, abe Gentoo Chovin aN an \ -@oEt —7— -& —Ciscoo Et pela ogy, BY- CHO A 5 Kis -F a ted ce vale 2 5 Gg Or Mca et As Gis “<= = cH Coot ~ ) Ms -c4 CHa ~Zooh ea ae |© syntnagig ob aypacctcods 1 ° ee F Ms A gi weet So DO aed Thao a-Tebalone | AcOH ch coo use 4 | os > &e 2 oo a NAPoyl ockcodd | ig am trnPoreant apetication in agias\bere | bac acd =x © sygtresia ob doom CommPhOvoriic ocr | Cooke ca CooEk i , 1 cz0 oe BY-CHy CHEE 7 Btn —C —CocEe hoo : 4 Bunlene \ ee Cha-CooE oxot occk.c cH - COOK eatin ‘ Wo C- Cook \ CH, - COOH ®s wa ob chal > steal O07 cae ‘ 2 By-CHy, —COOEE aly cooet Ago, A _s 0 Wad Oma, > - on mas) | daly AL v yealyalae os a coset. + HCOONG OM | anki Pick) | © sypenesig ob aamPreronic odd | mee me | cM Ms \ Im 1 \. Pels, | c=0 + By-Chy -CooEE > oO =C-CHaCooEL 2 ken | \ a ted = ih ye- CCH, voc bors SB Hae || \ ' oe cM Coot | Eki) old y * Woot d on, -COoH | Rety\ accko 1 } ocho. Wace —C-CHs, | |4. VMyDRO GORATION - Dibcvame Oda EO alwene “he gyiela aly) borame. migonediake TR mot Uaclated + ba ores! | LTA a ole Wwyane ‘oovation, the reaction va, obtained dnect}s bavame hee omit onion Kobbr addition token PIOCE eng CHEM, —_he oo ony OMa 5 Propene Thhen.oe te ene aitly! BeFeme | ag C= CH war CoM eco O | Come = CH, -Ch, 3- BH ai alwys) werrome [oon ariaiwy! Gevome wee ML | cwy- ew scha + Mg 7 [nets ==: ‘a \ — 8 eMC omy OH - CH BH Cay ee 7 _|ew - 8 8 Rac © (emo “OAH Chy- CH= CH 7 : enn) : b a | ong Se He 5 7 (ers-O, -cy% 33> bee ba owes | ATOl¥y\ GOMER . ebbecks > rene Edt Suogtibuked ateemeR ko atkeme 20 brom coraneg - TH guoablated berm nonaalley Govome mrebro guoatitubed ateemen, EO a Ay 4 We. c= cl Bic — tes oN x= Bale 2 Senos © az suogtatd aleene “May Rerome . oy O% “f ee a aa a) “, Co Ga oe oY ie amt gubatituted olkere pray!cm ews ory Yeod aBke 7 we —o— ONL nu N (ular os MS cay Hy mrbve Suostibbtd Mono aly Berame Olam agrticationg - ° wake wae | CMy C4 =O, 5 Coms-cun- ny, & J Cy Ch, -Cy- OH Naot oy Ms ow @ wy A w. 1 otc en 202. ol ' Noon @ _ Arwyy Gevameg Com be axidiged to Grbomy) Compound om buatment cuith Chvomicacic, Hy Hy Hy Bite coe evr | ut rr oO 7 -S) Mw G. NEERWIN - PONNDORF- VERLEY REDUCTION she Reackon involveg “the eduction ob aldehy Ae @ Ketones “EO alaorela, by treabwrent etth oluminum LagProporide Tr eccekA cl TAOPrEYL alcohol dy mown ay Heenwein - Ponridonb ~verlety Reduction, Cn On ALeCH RG) on g R-E-W + Gy —cH-M% X—— R- Suen 4 Hy- 8-H vekore, Barcooly she Reackion 1A neVoyrible. The neverne Reaction cad oPPemauen oxidation. Mechamiqyn’= the neackion Probable. mnvolven 2 Cyclic bomgition Stake C2) in WHIch hYyduidelon [pom “the CH bond ob the. a\uoride wigrateg to the Cantey) Garton ob the Ketone te yield te mixed alkoxide cH)ee Cocwn® Da Qn- (eure), be Ne RY \h s soe c ° a er ey Une TA Wome, a c R - a cyclic. Tnomaition Atal. — cx) a. an owns Hf ‘ y oe omg =H cy ml) An excep ob Tac Propytaicere! TA Uged So thok it exchorgey Gatth the mixed oluacide CH) to Woenote the neduced Ketone Ci) neds RY jomtoew ) oe UM BLN. ar (poune), 4 7: c money CNM Saw cv¥s7° Now 2Parcoro\ ebbela’- RAT me Reaclion iQ gfecilic bey contoony! Grou? oth Yeducile QrouPA Such aq clelimic bond. Noa - eke Preame bo the Subgtiate nemain cnobbected Applicationg'- The Reackion hogbeem employed to neduce ob on Solinated alderydes to ap-imgatinated alconaly Cus ca-cho — ALCocanea) — =Cly-OFK Ndewns Acrordenys Cony,cn “om AWy\ alcohol A\ cw ne CH —OA = CH CRO Agora) Seen ee Ce cias Croky) alcche! 2 Reduction cl onomatic Keton. a ce Saas MEMS . SP itg-tu-cny Arcthy| — ' \Colho AcetoPhenone — (CHs)— cH-oH1 1 3. Reduction ob olteyctic Ketoncy et ALON)» a =e = fs * CHa — cH - 3 De Cyclo hacene. \aene. Q-Cyclo haceme 1-901 Reduction ob -halogemated Ketoneg Avocktia) 5 s ts chs, 8 _c-cly Cus - du -C-Cly Vi chiove acetone ey -BA- oy TM chiove 2- Prfome| 5 Reduction oly leko Eqling” i a ° (Crp, ¢-E - co0G. Ms Agore)s J Tey -CH - COO GH ety Trt Heth Pyuvak ty cH = Cy 6 Synthega ob ceabrodicl a ot Hy - oe Socee ocatome otgtadicl 4. OPPENAVER OXIDATION Re she reackion ig the mevege ob mPV Reduckion The Reaction Tnvolweg “the oxidation of a 2°a\cohal With a etme Ea wage to the CovvegPondimg Kelone ob the alcoho! Commonly acd Ketones ane acetame . methy\ thy! Keke & Cyclo hecamane - Coremonlsy Ech BoA One Aluminium 3% Butoxide. oluminium iAo ProPoxide e | RiCH-OH 4 ay-E-cHs Acre Ne) S ow j 2 alcoho! Aceksme. ‘Soa esr Chg -Hy Ketomeae MECM)3 M Core eS wns Co %K ou R-cu-R + =— av alcoho\ C¥clo hacomane Mekmne — Cyclohexcamo\ Mechamiarn = wutexide Tack to | The alachel & alumimiuom rrenkiony bon aluminium deavolive ob the af alcohol aarc-ok 4 Gene) oo (Aa cHo),AY + STK C-OM | 2° alcohol | she cluminiom dedvolive neack wth acetone “to | bem o oyctic tromgition state hich ordengocg tmtanal hydoude ion tromaben, negviting mr the oxidation ob | Alcohol to ketone “at Ric? CV ar(ocuR, = w a (aa-cno), at + cus-c -Chy) — ° \ © we 7 SCH g RE-R + (Os? | A-0- AL(QCHR apeicesena = The Reagent TA Ponkiclony vAcbet bey exidiateg, Un Solunoted olcokcla. becavge tk doe nck abkect —the dootcle bond 4 hy - CH ~CH SOL-CHEC — CHE CHL AXenes), g oa “ y 7 avy-o =CW= CH-CHEC-CHE CH, on chs Acetare chy G- neko) aS-ockabiene 2-01 inci son occa biumne ‘L-Ome of 8 case 7 O- O Cash A -FS_— ANGENS) 5 oe ee Acetane - Cane Gedlene o-\oalereeo x a AX(Oc tes), Cememe, (aan ono Go a Geromio\ cibol @) Wee iy- onsebarebd arbcors A, rdogo oxidalion wrth amigatismy oly double band “bo fon ob P-ensciaratad. WeLOnR ow , Aw Genes) 5 x \ Recwy=cu —cn — cn —R y ecw -cK = CHO —R P. Berto Quimme | CL AY Oct Poe eee yO) Reekorwe z STERIL CMOLE Bos! CMoLESTENONE | 8 A\yKc atcha hove Lear Oxidited Eo YMC vetoney oF” . (coed, A ° on oe a Oy -ts > oe x cry OHM Bercbune hd. De cose) A -vecalLone} MANAICH REACTION NARCH REACTO acid, he Gorden tolion ob a \ydroginn witty Fovrroldabyte artes be BiNe PB omtno my tre Preatmee. ob conten ComPomd Cnbainge) ockive amd anmmania CoA 1S arming CH 2° Conbory\ ComPpume tA coed = narmich Reochiony we) > 7 e . a &a,_e! anon «© ry) pete a Ne), “wo xe Reem ara a 0S et OF ( @ 1 : Mi: NH ae -*h — (cw WN —CHL > Cur a . DS annh ne i on Qo e w —— Wes Go (ers Y= > (os ae « ot —W0 ¢ on 3) xo \ (oy V Rd cre! ee Rca CHR ex n— ow eX 2 : - ) sy nN {oH oO R On P- arntno Contormsy Corn Porn ApPlicanion< ——~ cr ° @ gyg-S cw, CHO a Gage wel Acekso Prurare. NG Ss wcl 2 Q Gis OO© Sptaesia ob THEWENE 4 oro Wow a \ i‘ DowRle a . Piper my yet c=0 > : ee . HALO Ome | Eo ceo an Wi REGION ae / — On forte) Accom Sucdmaldenyde “TROPINONT @ sya ols Grommnine en NO), s on % eo) ©xxZ~~ Ly N w < w En wolt 20) GRANTINE ® cy tay +ba x % py tay auth + Gepnn — oy om NO), Opt 9 a e. 2 Q “ BE cH -N Em A, chp SHck HOH & Cru NT Rotooncerys sat @ MIQHABL REACTION © The Bose artobysed addition oly Gormnpumdg Fenmng ochre netigieme BAP “Ee om octnctad clabenic, et ob be, —*ayhe (c= spe tecbonuatb, dnouing ) Dy known OB michaa) Reackion he Gf haweg, 2 adkive, Febyyteme, eA ONE Coed, horaruy . The Compound, havi’ adive alebenic toonck coe Coed pichael acee Por” GasoNO ' gts eM = CR-DOGMS * cwy(CooGNs) > Gag-CH-C-GOGNs Gory) Gymonmate Rodonc, eale ee—— GNs5on a oe 1m anes cu {Coos ) * Gisov a cu, {coos ), >o : : = Coo GM! = Gis- ie ieee Melee cul Ms) te , 2 on ra ah504 vO é pola Sq'=o —OGM We -CH = CHT s Me wey Hed = EONS erace os i. -Grs? ) a en(CooGhS ) Lw(GooGans ) ° ae Soan GMs — CA~ CHS ie ) om (CooGMs ), APRLICATIONS Ofer aby TH Conbowylic acids, Ch~ C0Ghs, cue Oh a b a mc-Goans), cw ~Coo GX ee wad c \ A\-o_ pi day\ Fomvate eAlen &y 2 ch — Cook, du — aon Profome 12.3 =v duv- Cook, ee) Vicada RO CEN 4 EISEN Cy 08 = CH OOGIG flea CH —Cy CH Coo GU \ cn@ Sypteain, ob nth ComPund Gusona CHy~No_ + CHy—Cr= CH — COOGM: ——_> My, Ss chy cn OR OO GS \ Cu -NoL @ syne oy onrine add, CG\itomicaca) 2 GW = On—Coo Cy “XC — = NH —cu(Coo GMs ) pena) ° HL Os C00 CH ~ omy 8 — ew —c™ a & wd > “Cocoa ns = as) Gy ALO NHL 1 cu- cow \ Om -C Coon GunAnic Ao 10 BELDIN GUBENS ATION Sn the Preyence. dy arcoraic ken Con Nocn. teo ncleou \eg, ely aromotic Adadyydeg Undergo Condim zation cee ave a Wydragy eboney. ~The compomd bored. kpom Senitalda, hyde Va noun 8, Bunbin i. Keers roc oS 2 QWs -c 4 ——— 5 Gag -cu —C- GAS Bevtaldaly ae Lydon, Kebme. Ce : . oe eorEo ty) rrechomid © went —o vhs cw 08 ow \ <> Gig - -EN w a Sa o*% eR te on ae a af os eo Ow Bm 4 > Giig- 5 —Cn — CHS Gly — 6 - on— Gis \ c APPLYCATION oe OM ACN, ic; ay Oar io ven wae i Nee cs ° a cua Gus\& Furom olde oO a 8 oe OK enlorc) neo SH Ph © asa ——> F-89eenern0a0n8 - i eoonn anna 9999999999 seaete0 : -N OMT* eyenieTRY OF NATURAL PREDUETS * ALKALOIDS, mea The = ALKALOVD Ocawing ovsomic ore, ALKALOWS, Ore. Baye Chanadirn & cont aimin’) clam Ma Helmrogcke Reni] ALKALOW & One ery Poimanoy & + bok on which Caakcun Powdine. Pong) wrotvas Prom’ ComPowndy havin ab (eagh ore nitbiogen ie LAK ned oly in vey, moll quamlilig EXTRACTION OF ALKALSIOS, A\LHALO\OR, Jeorreg . Covy roe ob “tre sorte obs Vario, pleats ocdy, malic. Torbosacocida abc GENERAL PROPERTIES —— —— The AluALOWOQ One vavelyy Colo lear , shai be. debmed a4, Nelivally ane CANNY bounds tethe Seeds, vost. prod & Benenrolyy occu O4 ex acetic « orolic. cibie Oryatoline non Vetolite. SolidQ. Which ONE imporsble am wok, tuk one Soluble te Ethamol, Ether. & Chiove hom che. Some. awolloidy Uhich One Soluble tn wot Ex Caml ome L@uida INE & NICOWEAol ation cb orale Fney PReoeeed RED PANT | extracted, with J) waters, netromel SoLNENT a piskitolion REDIDVE \ apreatad. with > ENOGrne acy Boag, arc ewroca og the Sowtoe Sot oddition ols Sedivmn contro ati€ \ extracked ith Nostovr sent ce Ether CHevebom tere of BASES \ By eam, nvaweate FYOP HY re aniduoll ComPownds ee0coa0 ecco ce‘eeoneo ©e°ee00000070000005000090 799999 4 ol A Mico TINE dine woah Tweportat G widely arabibata why ia. TEE coca, oi, athe aly che -tobace o\Kade ©) bem. Gp =-6F =x opi ally dive ComPonc nN Ms abuctiol elucidation Gohwha © ZR nolecstan Formula 4% xcoline @ By vavad tek, othe bee natbicgem clo, tH Ni one B Gagex ® omoanon’- Wa oxidixedy ath Lrobine rng, ie berms, nicobric acd Ga) daChvorn ct. Connors ticocie. ) » Which mndicodes brat. 3 -subaletsted Povidine \ GoWiy Na peel : NICOTINE Sh ashen Nicoline Mm Su\PhUAC OGL « CYyvidine 3 ~ wicotine T& Cook nN icon AclO —the boomolion ob WiceTimic Ac\o fromthe u wicalne + sb awerbat Niatine oxidation pucleoug utth a Side Choim wire arntama Pavidine BP Con Bra poaikion 2: SON 5 ce | | |® Repycten Creaiion E.natere as Side, Choin D wutcrton “bole, “twee, rrolenvleg ols ryaeaes be a) Lom REA Hy In dewvokve + wich nar catiy sestthe ~ eecevanos wicotine 4 satmratid, - Reduction = Coty. or \ . PUCOTINE wa Ghee chs : WW Cio M20 2 © wel % vec with cmcnscted ee Yodsc OG ab \aic CHER DG NEVER netod), ¢ vecctyy sonics ts botmed GrorR xb awactne Side Chain Gahoing N-neby) cehenebele, axpreang Hat “he Side Chon COON be na -richtyy | pyrraaire , ue HE ptt ob- ooch meds “bothe Psrdine nuckeoud, Cue — CMS Nico VE iar \soc : © nrtacine beema om oadition Podur arth Find T the, eocdd Produch & dated —bo trom Pavridine . Purvole a mrtg) onic “WA Reaction warcahy tat be Side, Chon i Parvole deovolive ancl. igh i anneths ety GisbghBnch, AEN SighMalion | awe = i oeS CHS - Kei) Pe) eee | w Vovidive — pywole PINNED Gy Teabmuab OdueouA, Su\wnnorA, “thy an Wears utth wth Gramine & aclicoad & ota te give HBr wicolinine - a wectxe ob suypruve0 4, & SOPHIA pune Bn aceba) POMS, oxolicatia ak Nicos adda, ob \d0 ~Qpe be & rictasy) ore cow an = N 3-ccely\ Pordre ada onmidne ny pricing & Yeack att, Bremme OF ec Preamn eG kimme - Wa TH heating, WBy ko grve dk OME nico tat Cardum Yydncri de, seution ats lee ACOCA. snolanic oa & victy\ Oomine ,e©oooe : ooana a ss eooon aaaaAD 6666 6.6 B66 6 6 6 200 nication i cw’ ies ‘ | zs s c= ae : roonic veby\ AULCOTINAC c\o = oae anne the alcove Racking trarcshy ee He sbuctave oe NICOTINE T& cry chySYNTHES\Q oS o ‘th St QS ty BR ETSCHNEIDER Riduclion 5 ~ Nook \ CH Succimonnide, nenetsy) L-PSWolidone, © i ve) =" Ss ~~ ds ° Bow HCO“ NW HSA anda, wy doow eae Boy Gig0u ~ NV’ chs Nol wt ooh = ? — NICTINE oH 4 sey dhs a. CRAG Sante cen Cha a Sa, 0 GMS ce ~ &y-r) Ww nye eo Peal —_ NLCoTHNNITRAALE, Rognesivem Bromide Wey aie Can one (ay oth ae Ww N-rYRy Ww 9 = Svea s ) Woon v -WeY \ nt w NA, pa — (EY Noy STINE GD = NICOTINE.PURINE ‘A. CAFFEINE CPORINER ) cabbeine ig the weak impertamt retires Cccuving, Xambhine. dowvoliver. Tb UA xanrkhine Boat. | FE oceuva tr tea cobbee. vete Cabbeine tR a ColowleRA CamPound . MP 238°C Thin a biktin tm tage € Soluble in woken & alcohol TEU a weak Bage- Th bamg Salty with strong acidy Modeciraly Cabbeine Va ugchot OM: Sos ee 7. VAR eed Weer ne > con Wt Te ye oy ot + bs eae des wad-W Methyl xomthine Cov) WIA- MH Methyl - 26 -diby dross Purine, Sbuctinat elucidation’ © =z nolewlan Formula ta Ce HroNyor @ om weating wlth HT ak rode - cabbeime gtveg Three maleg | ck cig& . which mndicatea the Preaunce ob Three nets) Soups aur CAFFIENE Co ar + Xorrbhineg aoe © _oxipaTion = ARR cabbtine on Oxidotim with PoteAgium Perchlorate tm Wel Qi Ud-diney! ONorm E Heyy WE ° x caprene KEM ytewn-donway 4 HCN ze Kel a =0 ono neds) wren, oFNN Hy \3-dinddy| alloum° ° yao & - & = coo! Hyc- N= G-NK- CMs, 4 Wool- © aa pen’= dintethy) wes nese oxalic acid \d-dinethy) alloxtn athe atone Reackiong Indicokt ‘thet caleine ord Uric acid have the Somme Stelton abuctive omd ‘ae Porition ob by rethy\ GvouPA ama me Tey Fon atam ane RO ls ava wretyy\ catobilighed. Thea the Predict the poaibon o sour & ard aggenatem Thachore the bellowing Srelton structive bev colkeime Aummoriged the albove wabermotion: The SY methy!! Grou ak thoy Paition 7 GO) 9- cmd the Renaming, cy den | otom ot 6 OOS S. a aS nN =n. wen EW Nos | ott g 20 tN 3 1 Ms poaition oly Sve. netysl Byer Flachtn algo Uolated omathen oxidakion Product agrich an NYPOWAR DNA Nenethy! gigcine, Coa amd Ns. | | aw, the BA oxidation Product yang be N-ncthy! hydamboin hy N a we Ae : wo NH - CHL -Cooh Con 4 NH \ c= en \ 0-5 Ny 7 wen yp 1 Cine 4 | | cree bere Ze Contain tise ning stuctivea | that ob di nets) aloe & N-neby! Wydomtsin |JoThe Following tie Skelton Sbuctive be & cakbemne ane Powritcle. Sence each could give “the nequived oxidotion Product . | Os eS Cc iy ZN, | Wec-n% Nc — Wc -N en \ \ € e Cay | oF N\n7 Sn 7 oy \ ow | oe bs 3 = x Finally FURChen iAploked amsthen oxidotion Product ytdi rethy! acorn ide. » g 8 Co) Cag-nW—G —G—NW- Oty CAPRIENE new’ = di Retin oxanmice The cxidakon A ony Agile wrth the chuctie I. So Suche EF tg-pe Stettion ob aobbane, cH: ci ‘i Neon 3 AVY SNF Ween buy Festhion ob ayygen oben there ane too Poaaible- sbuchwes her ca bleime om ee Ta ne Wac -N a Wen No 8 \ WG aS ae x \ 2 cso ioe . oN S27 \ — hs = Bcvs | CAFFIENE OX, chiovo cobbieme MOM __ mrctinoty Cabbeime | eewotson, aha Nyon. ct HHMI OCHy, nol ony colbeine + CH Cl | ao, | Bhady or OH | Oxy cabberne. wor identically ta retryt ecacid , sheebere tre bollowiry, stuctiven ber oeyy Cobbeine wy i ee oe oS) | Woe’ N | \ oH Wye ° oe, a om 3 ee : nN os de & w when oy cabbie ax i silver Salt“ heatid, Cstth Chet. TE) Convented into Oo weactre ob tea net) UaCACA CuhIch Containg Four N-REERYY Sroupa ) onc ethos cobbime C which containyy three. N- ) BvOUPA ama me nethoney, group ) ° cay ‘i wen 7 8 wget 2228 sa he chat oN - oFN ‘ dus cay Ow nedony coline = retro. rey! alkene he SimuitameBA bermalion bene Product, Suagest thak the oxy cabbiime ty a tautomen.c. Gubgtemce. wk contoina the armido, cmnido\ S+& bern | | ate glmcbere cb Cobbine conbirmed toy ity Gyrtherig | : ecSythe aia ol CAFFEINE |v migener spyreeai | . | 3 4 7 pols N, vac" 7 ~N cH \ | vee T Ye — 2 Pocky ay ook omtN ome \ | 4 Ms wc ocd, a e 3 pw Da * we ee Wot-n 1 Y eae a \ w? 3 vi? oa oan oe | Chievo Cabbeive. CAFFEINE 2. TRALVBES NETHOD ~— ° we now th A” ae conc oe te ne Wor, o= cm a sylere NAL > | Nw me 7 oN 1 | Oj cH Mt co eyame etry! nant dt ney ocerate wea a = | 8 Dm wed eo yo TM\AGH t= oe : Ween — oe oc hy” Net Rete AN 1 os owt wits 9 ree, oN CAFFEINE, ds dB. grevercckS Symbeata > PREDES =— o oS ad ~~ Caw)sou teh er > oot M7 The YY ion ok y nctres lou s dw CAFFEINE {CONFIGURATION OF RING STRLGUREQ oe oe i. By cARgeWYDRATER | y Keone anc called. Canto} eraliy poiy hydronyy aldehyec® cor Ipore Green Plomby: HE woteraly, E cam be Prepaned Called. Prato SyTEneAR GCor + S40 oe. cunec * SO | Guwces® + | Giucone VA beond to lorGe uamtiti, colled Grape Sugar. Srna! tm viPe Serer | amd hence “kre rome auambttys | oly glucage TR Preaert m fwmom bleed. & NE | Prepanation> | hen came gugan om Wyydnoby ai. Prememce ob acid to Swe grucoge & PractoRe a watth woter nthe + Wh enna * Cede cate Mo FroctoAe SucrvoAe aucons stuctve cb GuoRe” ens — | © From amalyzia & the smoleculan ewegnt dActiwmination, cre noleclan For uta. ob glucoge tA Gn e | © Pregemce ob S-oH GrOUPA™ | Gaucone Va Teack aitth acckicamhydude Cov) Aceky. Chiovide to berm pentaacety) deavalive , “ThiQ Show | tthe Pregence ob S-OK GrouPA Tn GiucoRe ynolewle, | CHy Coch cKO | 7 : i (en ocochs ), | : | \ Hy -0 COCKS, Perka. ocetyt doavolive Glue cH) Gn (eng C0),3. Prenence obs Cantons} SxOUP + Giucene neack Orth Rydrcry| ormine to bm adda ony one molecule: ob He to SWS neactiong tmadicate “that Preaunce oO ketone buk not testy monoxime - cyamohydain THEAL Cithen aldehyde CO cu=Nn-on cGwncg + WN-OM aut \ : Canon), Wydrcxy) arenione ; a Chy-04 nonaxime. 4. Pregunce oly adele Qrour fy Glucoge an cxidakion twits Bromine wot to sive Buucamicacid . THR neachen mdicatea the aldoyce Syouk, wma ocenh'y sine end. ob “the Chaim Bromine cook Mi 1 Grn aes 7 Cenowy CryoK Glucamic Acid. Glucoge on axidation uit strong cxidining, agenty stig neaction tdicate end. aby “the. Chain. & mathe end, ob “the, ww like Canc HNO bo Swe Sacanic acd. the aldehyde SqroUP muah CCCUPE) Me Prirnaryy alcoholic Soup rng COHN chain cook Core HNOS 1 GZHnOe —— nok), \ cool Secaric acid GO Glucoge reducer Tolleng Reagent to metalic Given. vreducch Feniling sdukion to ned cofrouR oxide mis neoclion burtren Conktrn “the Preaunce ck tewrimal aldehyde, BrouP.abr Cone Choi ae with TA, Treduced* Sodium - oma} aoac alcohal Us obtained the, S- Nabe them GIUCORE ko give Sanbitel om Wyanogem odes CHE” Pregence aby Red POAMREOAR beg BNE A MEEOME TERS fanelsona, Endzoabe ttt, oa conven atama Preacne eight chain CNo-43), wecony' stn ro MA: i \e aM: Gunes 5 CMH Eom EMT MS Read P = ans HETOME eabed an ateve neackion& Gag S453 Baagins; the bellowing oRmchain structive ber Glucone on ok «OH aft rot ‘ wed —e— e HE THEW MO 77S yy} wok wow OH athe, ORmchain skrchire. Contaima Four oxyyrnmel a cthenebave. TE exigh To fais optical active 1g optical iLRomena anc Known Derecka tr oPenchaln stactere “= a no emely opemchaim Sbuctive. Gontem akon’ - berry. All theRe fetl to ceplain the Following, wat SWE omy colouy ett Soni > Reageat @ =k dow amtain am aldehyde QrouP. iE docg @_ even though Dlucoge mot gwe addition Product wtth Sodtumn BiSLlPhite NakSo3. amd Amrnania, CNH) @ Aw aducovg Solution ob Glumge ShowA muta Rotation ic the Specilte Rotation ob of-0- GlucoAc Sradunliy balla bam ilo" to S2-S° omd thak B-D- Glucose Sradualyy mereare, fam 147° 0 525° td nent ee — + ELwy | | | | hh ® Grecoge when treated with methyl aicahel Tr ayy Het gag Bde a mictave ok two Uemedc methyl alucogides CaP). OPNChaim Sbuctie Covld ct explain mthe, bewmation ob thege Bluconicder. a lo Ciomtolee abAorption ob slumge im at Sclukion docgwel adtcoke Chonactngtic bamda, abr —CHo Group -Hemce ik ty Concluded. that aldehyde QrouP Pregent Tr Glucodt smug be asmamged th Some Gi. Cekemonakin ob Ring stinctive ob Glucoac Glucgze doe rot give addibion Product with Sodium 6iSuiPhite & Ammania. Glucore exhitit mukaRotalien Glucage TA neack wlth metiyLatcohal & Hel to Btve aomeng ob XP methyl Gluconidcr . she abave ProPerticn das nat Similan te the Propnting ob Gluck. The abe Reactiong Indicate that stuctive ob Glucoze hag no lec aldenyde BrEP. buk the Aldehyde SyouF tA Combined with cthnatom. Based enthe Stability ab y-lactone Flachen & Tole Proposed the Fuvomoae sBuctore ow Ore c \ a i W acaet = ce 1 _ é oe wo- Cc —H c : \ 4 -e-0H Lane -e—9 i i \ w—C-OW Ww -C—OK \ ‘ Y-Lackane cack cuoK Crtim Stucke Furomoae stuctive aon Furamexe Stuctive -the aldehyde Canbon TQ asymmetric amd it 1 inalolved tm two dibbrurt, AWORe stuchaen CX GP)