lew laers t CHAPTER It ———}-—__ALcoHols,. PHENOLS AND ETHERS i200 |. Aleohols 2-04 S > —The_replacement of ene ov more hydrogen atoms of aliphatic hydrocarbon by hydwxy groups CoH). It is Hat ny droxy devivative of aliphatic ydmearbon. MMe ehennis Cie ice ua ace, a = | The replactment of ono hydyvogen atem ef benzene by hydroxy group Gon). Ik is the hydroxy devivative of —__—,hen2ene. pooh vaca oH Ethers ho ety OD a this the alkoxy (0) com amylony(-oRy) qrouip. Bean aa a XN wv Bee eo. Allylic _Benaylic _Vinylic Phenol + Based on no. of OH GO RS ie la a ee _=> Monohydric mg od Sak eh a le ei ats th Oma -0H groUP a ee pm ie eRe at AB CH, HyC= GH ch) Or boca oe [ort=> Dihydric A BsousS | Alcohols having too “0H grurs | 4 Sashes OH aes eS We i —— | CHy-OH iéss Se e L “he Tiny dyie SS + —Aleehe|s having +nree 0H gonps_— aaa} | | | i 4 oy OH aaa + a 1 CH - OH 3s i Be Se iL \ oe CHa - 0H oe ee 2 a +, Based on Hybridisation : Csp?- 0H a | -0H grup is attached +o sp? hybridised carbon _ | ef alkyl group usin 422 Ally tic alcohol _ oes Sane | OH gxouP is attached 4o_sp® hy bridised cavlen next — Pe Ae bod O71eal Based on Hybridisation : Cep? ~ OH a Pot ne i =DH gvoup is attached +o sp® hy bridised carbon _ oso group a => Ninylic alcohol cia eh |, bH_qxoup_is attached to sp bya iehelgia te |. nax+ directly +e c=c double bond — é Cn = CH -0H wi): Seen eg Me Pe ore Bhool. : se ee faa OH group is attached directly 40 sp™ hylevidised — arma tic _axcing &. ON SetelssieleAtion Ethers Vv Hesimip le “tor 8s a Sows ae er eect Symmetrica} __ ons Unsymmetrica allsyl i ony! FN OEIC cl te nye atom __ —~-_—axre_idif ferent+ Derived from com Hoy adding alesrol in ib ——___|_-Chy on => metry |_aleokol —— eae — => \UPAC Nome: men_name sof alkyl 97s Pp: Folly oe | Were: — Derived by alkane name by removing @'- ond adding ‘ol" Compound pacer cand | term CHa-OH | M | CHa CH -CH2- OH 1 ee ae og -CH - cHa | 1 CAS- C5 -Cty-cry-on | CHy-CH-cHa-cH, t OH. CH3—CH - Cita -On ext | h- propyl aledel |= Prepan=t-el | isepropy | alcohel | prepan oleae burton -l-o| n- Buty bury! alecho! | butan- 2-06) buty) alccho| __2-metty| propano} cneopenty | alcohol (2,2 -dimetty) | propak-l-ol glytrol | Propan-1,2,3- trio) 4 Cyclo hexane Phenols ~Crenem| Name: Carboliic acid + Derive im He eC tee -behrene group , foUn wed by —NOMENCLATURE "Alcohols -=> Common Name: — “Derived from common name of alkyl 9704p, Follo we, CH, 0H => \UPAC Name: adding. po | Compound cH3-0H boy adding alcohol init > Metayl alcohol | Meta yli seo Derived by alkane nam @ by removing 'e!_ fbn A lUPAC Name ~ methano) CHe-CH2-CH, n- Prey! aledeol ~ Propan -]-o] | | | | iseprepy| ateolol prepan - 2 -o] iz bo |e n- Buty] aleoho| butan-t-0l | | ee ee | coe butyl alechol | butan-2-0] lager: Cee OF isobuty) alcohol | 2-methy! prepanel m= com neerenty | alcohs! |aj-dimettyi LL co a PrOpah-l-ol | be gly \ | Pre pan- 1,2,3- ie trio) Cyclo hexano|(UPAC Name Phenol | L | OH : ¥ _totechol _ Bem7end = 1,2= | So j - 7 - diol 1 — Oe _|_Resoreinel | Benzene 1,32 oH | $$} © | Hydroquinona (or) Benzene -1,4= oh | Qvinel f | | WT + : on F : sets “Ot PyrogoNMol | Bensene-1,2,3= a triok a Hy drox yauinel | Benzene 1,2, =? Common Nome: + Ethers ove generally derived | from the nanes aly | Jory\ gveups written as Separate voords cies alphabetical order ond odling to word ‘edrer! at tte end a R30 ty bte > Be =Compound IUPAC Nom common Name e | CHa O- CHa Cals -O- C2He Dimethyl ether meth ony | methane + dl Diethyl ethe 7 each ane | pe SHa- 0-H a ca Or, metiyl propyl Mettrormy | ether it propant le on asd NS —— $$ | metty! pheny! Metro xy . ether benzene CAnisole) Poctnulpneny| eae ethey benrene Cpe neto &e) “Heptyt plunge Phe nemy t Sp | Geli -0- ce -cHz-cri ~cHis | Pheny) iso pentyd | metieyl se prop st | a tee 1 ethey Propane benzene \o2- dimetorxy ethane | a- wan eugh becheptany | _——. Alcohols +. 0H sigma Co) bond tsi — — “Overlapping of sp> Wybridised orbitals of carbon amd Fe ise bt id ot 0 ls ae oS — Baek te: nahn xelis dedi ee ———|__slighily less than ala aalvall ghee due to Hoe. —Y€pulsion between unshored erecten pairs of —Xygen + Bend length: 142 pm ———__i' Phenols) ee zd ———_}—-0H sigmate) bond’ _ £ 4 — Ovelapping of sp® hy bridised ovbital of carbon and —_____sp* hybridised orbital of oxygen hee Bt ond angles 09s 2) ee ee — Almost te come os “ele nadralyis oe ——,——_bhae_lene__ pairs of, oxygen_ave _involved_in__tonjugation _ with _benrene ving piel es 2) Sie Bond engi. oh ene isonet bond Ethers. | 6-04 sigma Co) bond = 4.4: overlapping of sp? nybridised ovbitats of carbon and _ PpLsg- Pt St Batid lenotes. | el pe A Se Srtcll EXPECTATION. ot Bos Daily fe+ ExOm. “From carbohydrates - From alkenes (Stn Se az ACID: CATALYSED HYDRATION (Mariecnilecw) i). Protonation of alien electro philic attack of | 30% ion to form caxbocation. 1 rae ae te Peabo WO > hye oleae a |e Eanes, a ft es i 9 1a ee at i Nene cst cr is —fropent_________tisa paopy| alcool (a): |=> BY_HYDROBORATION - OXIDATION Canti- Markonikoy) ss eats pe 1 eases’ apt gegen Acideiq\ ja fn oof ka eee tet ay Alkehe + (BH), —> Tialicy| borane —_CAdduct) Step Gi) Oxid ation ee 5 20a J 44.NaoH Gn: } pH = tpn as CH 3- CH» - OH i} aes, NaOH Hee tie Wie ws kis. ——Hbhiningt 23 1053 co W/oH © crs eae tH, Stepliid: | ee omg Final reachons— [eit Heo + Uta Nig C4 ———> CH y VSING OTHER ALDEHYDES — 2 Step Gd) cg tH + CH -Mg 4 > BBN og : vi | eee 1 cet i Pa CAs. Wiio nc rete ; Wi Stee Gi}: —=Sc- omg tl ——> Fo = OMG (ory) Ch aA H*/oH™ ieee a | cus, adh Cee E fe Pe ee anon dieing tee 6 evote da Se + OS 1 >CHa-CH - 6H + Mallia. = pep Cg oh Ot Mg CL | GD a a 2 ae a): res Crt, 3 HL0 crt > | to Hot Mg CoH | Scat,|, final reaction: eg : j—U4s Coc, tits MgCl ——> tH, =<. 2 Vie i eats | | yp see Ce : From_alkyl halides _ R-x ete ee I peor —_ Catalyst: 4: NaOH /koH eel oes bode SI Frem_ i’ amines 1, RN No NOD EHC z sete + dH,0+Na@ | Roni peChin tally o1—— PR OH Nig Meese] T= fam carbohydrates Se Gt 0, ee eC, Hao Sucrose Glucose Fructose zymes 1 Co Hi, - > Q2CrHcOH + QWy ae Ethanol _ + From Penrene Hareniumchloride 3 Soy inn CAN A LC lg| From Halo arenes i at a L i): | OH +- HU —$a3}7 Boom Wesoud ae Em jh 1 ‘ a Hie 5: [Unlove benzene. sodium phonon e EE ak +— OoNa ou step Gi) scr © aa L eae Nee rr —— | dium phonoxide pheno \3 + | Prom Benrene sulphonic acid —__— a 0 ee ee = step Gi) Oo _guewmnltas03] iy pillar | furning 505 oe Hi | Benene Benzene sulphonic add AM Se ee - Stee Gis NaOH subst h dn ee Pe |S mt aera + HiS80u | | Bemnene sulphonic acid Sodium phanaxide = Ona ou aae a oa sep), ple dd toate F Seinen oO + Na + HCl es tats warm pik AE Mea sei | poe. Siieng suiliod Pe woll) 2 ee ees OM curmene ae apf io Phsca WE Cee eave Mje-COCH 14s Jord pine ee = joey © , 4 _ Camene Cament hydro pevoxid € on Fd jctoon a mn ie = {9 ESS 7 tat ++ CHty C0 Crt ____.Gumene hydro perride _ Plntwolhé~ batterie 1a ad _____ Physical Properties of alcohols and Phenols _____+_ Physical _state + ee omen a! coho} 3 They ave in liquid state, celourless have a pleasant smell and burning taste —___2>Higher alcohols 4 tae They are_in sclid state , colourless, odeuv less and peeree oie a eee “state. they have a lig hivpinkish colour or are _ wilourltss . They are deliqui sent materialsfa | i Beiling point (=> no.of carbons &% boiling perne | Reason: surface prea , Vander vaals force ? T r ———}* No.of Ct » BP > SAT 2d vi. force T | ao mole => Branching ! Wee boiling poink Reason: Surface prea, Vander woals force a Eromelung “Te> BOY => sa) => V. Fores es =>_Rydingen bonding ok heilig Point Hil Reason: Mass of compound Oo TScies | iL ssseaslg fp paaieio.) Mabe toed) is ee }%_tl-bonding T => B.p + F ul | rio ee St 5 ial aa F ST ieee i Molavmass => B.p > f | | | [> WMPOUNDS with same MoLaR MASS (Functional some r: 4 Alcohols, etneys ) | |} $f tas HGH BC os CHa, Cts pe ee Ne cy ee Rees ee |B. P ES pata ke Sei " jWhy does Alcohol have more boiling point than ethers, | Haleatka nes, Halearenes and Hydrocarbons of te same molar mass ? < i i fe 4a 7 ae | pleomelS have more boiling point than ethers, _____|| Haloalkanes, Haloarenes ond Hydrocarbons because the inter male cular ly drogen bonting Haat “takes placw im alcohols. oe © «| why eee Ae ae Eiduemeaecel ethdhies Mee eniroholsut ie ci os eel Phenols _have a higher boiling point tham alcohols because of the molar mass and carbon chains. _ » Molecular mass fee Shs Shurfoice hay bat (eaepitt phe nal = s ili) propanel._tashighet boiling. point than butane - |i) boiling points sf alcohol decrease vit incnoo - | Boiling point : Pp >m>o melting point + o> m >P + Selvbility => golvbility ov. Hydrogen -bonding— a 3 => Solubility \ premiere ese | No: of cavbon chain — a pas City dre pholeic part) — soa |e - Give reason hes e ome. ah nor i) o-nitvephenol has lower boiling point than ce lh sony ett te r ss li) pleohols are more soluble in watery than the L | hydro carbons of tomporable molecular masses > i Es pin branchingsel alkyl dean } _ |) poili rattnk staal et methanol : eS : Vi) boilt i E ing paint of ethanol is vi + matt ony methane Mex than Yat of | eeSs es see vi) Aleohols are Comparatively more solu blée in water than. tne cress ponding hydrocarbons Nii) The GOH bond angle in alcohols is slightly less _ than the tetrahedral angle jaca ee ate E ng points of ethers ave (ower than. tne isomeric alcohols 2 8 ey os a pa i ms re alge 6 = hike phenol ha: inkra mole cular hydrogen bonding -Ponitwphenol has intermolecilar hydrogen bending, wter molacilor hydro gen bonding leads too molecular 5 asspriation, (This increases the boiling point Mere fore, — Hite na le cx lan mass and surface avec is Hencd, o- nitropienol: hos a Lewer boiling point than Poets plains belo heaean Pe 252i Due_to presente ef -oH group; alcchels can form hydrager bonding with water but hydrocarbons canhet form _ sudh hydrogen bends dueto tne absence of tro -OH ponds. enw, oconels ano comparatively mare soluble in_ water than hydrcarlons. of comparable molar masses_iv), ncveases. Hence etranol possesses a higher boiling} than methano} | i-tthomnel undergoes intermolecular nydrogen loondi ng | — _due to the presente. of o Wydrgen ottached +o anc eletbenagaHive oxygen atom. Ago result ae | i j-peimk oP ethanol is higher that methoxy methant— water and alechols axe both pelax in nature. ihe . Ww We nleaialstrctas. petlikneapeinesowectens® te. ; in be caus imeware of branching in cavbon chain eO8 He decrease in van der waal’s forwes with derraase dn surface anda. As tt number of catbhons invwases, +L boiling | point alcohol increases. For alcohols, boiling point depends on yonder waals forces too. This force increases as the length of the hydrocarbon Chain _ ethanol exists aS ossocinted moleules. conseapextll _a_large amount of energy is reqmived to break _shese ydregen bonds: Therefore, te boiling | wobich dees not form lydwgen bends. | _sverefore , alwlols are readily | oho reas yd arbors ave not an alcohol is dissoived in watey, it forms ae ia form wydregen bonding tlt, vogter molecules) }Solulble in oat et |Ad ond angle in C-6H in alcohols. ts_slightly tess than tetra hedval oun gle C1oe-9 "lb is due +o +he repulsion be-toeeh the vonshared electyon pairs of sxygen: In alcolols , 4.0 Lona pairs of ele: y comparatively more ond less bond angle 8 iis thers CR-D-R') cannot form intermolet4ay hydaegen bonding due +o +2 absence of HW atteched _ woth the elect vo hag ahi ve atom as Nio/F, bubtin _ He _care of alcohels they have -c group ohich _ Cam undergo intermole tulax hydrogen londing ond trot increases their boiling pointe Chemical reactions of phenol and alcoho! Aloo |S ond phenols ang versatile com pou = act os both nucleophile and electrephile[ee ll aa i = Reactions involving cleavage of oH bond 2 Reaction with metals 0 Weds Acidity of aloohels ond phenols. ES Ester ficahortie sheet oa —-- > Reaction with grignard reagents Repeat ETB Sees es etal ¥ a —) 2 Ren + 2 Na —>2R-oNa + # i ob. Alcohe |/pnene| _____Salium alkotide — 3 2_Crts OH + 2No_ > 2 Hy =oN® Hy = Se Mettonol ae Sodium alkoxide CH e —tH3-6 =0H1_ 4 fee eee = fone Soran ie t ae) cet. Shi s f Pal . ONG a Which is more acidic? 1° or 2° ov 3° alcohol ?carbon which acts as. electron withdrawing group due +e the Charge distri loution in tho resonance Structures | cA reS oxygen ef -0 H group +0 be positive results in| polarity in the 0-H bond pwhich is more acidic ? phenol, water or aleohol. | — rearing oxderef acidity: Phenol > water daleokol —alkoxide tow , negative Crorgesionetocalised on — 99 >. whereor in phancxide io, p negative charges -delocallises, making phanoxide iow more stabl und: foveurs ionisation. ,-0f Subs tictuted phenols Electron voittd hawing groups. incwases. tte acidity Electran_dona ting qwup decroases tc acidity which is more acid ae phenol oe | cect i gxou ps etc eee imerwakes Ate acidity of +e__pltuol ond witr group (=No.)_ is oa elethon withdrawing group. Therefore, o- nitro plenol ts mere acidic than Phenol duo Fiesta ted a teaateczsnu. | a it eps a aaa apnor pheno} > ps — 4 eranena ee eons Woe eR ee ot =k ttt <1) Bleclwo __Corbaxylic acid ester _ + ACID A NHYORIDE > ESTERIFICATION J anhydride Jacid lovide| > Ester ae Alcolol + Carborylic acid /aci CARBOXY UC Acme : ut ° | asi Ros te Re ek SS Wc -0-R + HC] alcoho) acid cMloxide = Eg dev | eegern FO ct 2 at ray . BPRWS es Bool treo! = Ri a RePEc HR ee CSoy | —Alelel acid onlry dv ide, Estex __Caxbomylic acid] i a s Tt 251s 1 PRetD. CHLORIDE: ee ae 6 : |S * wl ) Frepone met letromoate using ethanoic agi i) prep. as ake using ethanoie agid £ —CH3- 0 H+ CH Coo => CH= O-C-CH, + E50. metaanc) eee — ii) Prepare metighteanaate using es ee (tHtg= OH 4 Utg=C-0 ible eel erig-0 eee metione| ; ea Se ae Vii) Prepard methyl etramoate “vaing rid’ ne ° : CAO MSOs eC, CHy-0-8 Hy + te | ae noo Cus ee Me ee May el p rine pro -preponnic acid | = a o Me 50-6 “Gis 4 20-4|.) Prepase m org tect eg fey peld 2 ee 2 eee : 2S ee _ Phenol a petty | | ee Awtylation 4 a Intyeduthon of anil grour (= Co CHa) in olcoho ls ond phenels is known as acetyloction —— too __ rt a S —_|uPAc. ai. Sass Common oame: Salicylic acid ses of Aspirin: Pralgesic os -—-- “pnkic inflammatory ee on + But ia pyretic — bibs cos hee sei bias a6, ‘A “REACTION WITH Hx, PClo, PBrz P43 ,S0C!2 Rout Cle RAC Roly HC Reo Mt OT, FR - */r Roo + SOci, ——_> R-cy +8 02+HU jhucas reagent Test a is ag 3° aklco hol —> Turbidity forms. timing diate ly | a abeohe | > Tuabbidity 1 H— 12 alccrol ——> no turpidy. ty formation. + DEHYDRATION (From Vin Nic_aleohol) me BR rg Seat itil Nid SoM im J anaes ne [a oh | lenditions: _- Protona: Re 2-5 minades ——|HO NDE ies a 4 i Seas aa 1 abcolel vndargoes dle by dia tion, in strong conditions — 2° and 3° aleelol undergoes dehydration in weak condition: cone: ¥1$04 —— $—CHy = Crt, = Bit ert cree mbt =e Cbg ate bt Ol ie ee alcohol bthy lene tone Hts SO Sh Si bity SG SCH CH = Ort ee i ty CHSC CHa +H O 443K But-1,2-lieng, ites. EE = CH FCs tM AYO k it 1. “propyl leohal Siti in BO pen 1=-Ope - : ejo oF H3POq oe c ek BIBS kta, = ce = tus + HO y 358k : | step Gi): Protonation & alcohol| sheptit): Jeprotonection of @Nbecation to form alkene a van Wy + H-CKRe® SS) ie Get H | ia : Leet + OXIDATION [DEHYDROGENATION J 3 | i Cod : A Sion 2 >, pldehydes | ketones ———> GArboxylic and i} | 4 Aldthydes: weak oxidising agent (1° alcool) Carboxylic acid: Strong oxidising agent (12 aleohel) ketones: weak oxidising agent C22 alcohol) 4 _.Alkents: weak oxidising agent (8° aleohel ) 13 | i“ Strong oxidising on [weak ox dvcing aoe ee pete wee DOA - Rudified KMnOy | + Ags2O _ | | = pidified K2Cv2 04 — + Pyyidinuum curate || | Disc vivatel WSO annie eecoCeee. ||—— cul 543K sail ae eh OH af (ag eed ee a ___demetlylpropens _ aif; = 0 A V) eH cits of avai be cH3 COOH ae ethanol E J Lhemical reactions of phenol —€lecty? philic substitution, veactions —__>_nitration S RUBEN AS, = x Gi elec bclaikyalon sheers i => Friedal malt acylahon a | + Kolbe's regchow - iu ieylin acid NOW, co, Hl —+Riermer = Tiemann reatHon sutinsl -eichelaydes ort, aq -NaGH + Reachoh with zinc dust + Oxidation as ae =I) Pee ert Sees Turion Rt AClONS ee ,O-n eS OAS elechohdsmating’ que S benzene rin 9g = electron wwittidrewwing g:oup (econ ct Tey ane 'o' and 'p directingjks inbermalecutar | volatile than pleine ouse a Waglaog en loon deng on Ou ; ny Noo ———— eee ay NO ed | ——__—_—> (pickric_acicl) | aa Now i . Se | _ phenol ofr, b= trinwhro phonel (less yield ) th ~ “ On Noq pidrabing mixture er aiid ie © FINDS cone. 1, S04 ae ! ae See Oe ee coe. Baur Ee ol oo eee 2G -tanihophemal (more yield) a NoTE: a s Wee 13-nite_g ups. attack Hie ben 22 ng. ring. AS more Hiss 2- with drsiwwing 9wups ore present, ot bend becomes L more poles and HK (an be released easily. => Halogenadion oH ou te it ae ae eae) Br, (CHA; ie See fees po Bee es) ee ee | S Nbr / oi oO os Br bite! bon “a po bromo pheno) (i =| 3 BIO By ey a ——x»> ~ > e;— > Sulphe nation Sa Decale i CH C1g. stig aig aa = 400°C [eee POung _alocchoadialae an | SN eedolcnabts! © | 3 ire cls Nba E I eeercepacobsle ees BIS as a One igh T and ; | |=} korbe's REACTION | 2 °. INO i Vie roe eee oes | poy an ono ONa Oo Se_kolbe a Schmidt lee i eee ON& no | rey Poe Wao” are ne eel Phenol o higinasy benrnicg pitas ae cl | {| I. + | RIEMER = TIEMANN REACTION s Onc cHels ale Nad 4 Bee Cor odiat eo Ee > ae . CHC Noo . Wee -QNa $4 — t Ue ae Ss CHO =o a Se > ot Ll ZO ‘ a Salicyl aldehyde I REACTION wiTH ZINC Dust+ MIMS Test | Phemol turns blue litmus fo red but alcohol Be ioe oh. sec neeee + NEUTRAL Fecl3 Test Phenol. tums into vidlet ey blue-green louy rohile — Haleoholsidio: wot. Balt siing cba gi ee Phenol dervolourises brming watts ond forms _o— white precipita Ge: toile al colo A lol ao + | Br, /water TEST oe eur, EST Cio SOFORM) 7 ty 2° aleobol > yellots pxectpitake (ord ef ae 6 Leo | => dees not maritit ia seit sgt phenol —> does not.fomm yellow prectpitate —__ sal Test 40 dishnguish ateolols phenols and carboxylic acid i aoe oom oobog}n ey ee oe ee “aR Bon ATE AND BICARBeN ATE CNalteoy= se N94 000g J) ——_____ FR piesa) No brs chasse = cio tly. important a lealaa bs N Some ComerPreporotion: torr byo 220293 cHy 0H io, 30 S?3-b93k > 2G HeOH + Do aymnase *tlourless : Boiling point = 351k. pe 2 mildly injurious ——__ a Alp nt _in_poink +Sowent 1% paint __| ______ |} 04 vemighes 2 | on lab! solvents om © + fet making aldelydes __|+ used_in tek of preparations | preparation ofstthers ton 230i 2 {asia tS + Deh aphser olrpholsen seoh See isk y aie + witliamsen'S Synthesis _ BI ale E Sines NE teint 3c sub e tae Sah a 4 wD tinh of GON ea ee ; ene RiSoy, ; ; LaMar’ 4 SReaeik nah commen ae sth, 0 | toe Sbavloolee Ele chro philic attack of pene caleohe | on _ | eunothersalcoholmolecle 9 22 ee One oe 5 H : a Zi O43- CHa = 07 Ht ety = ct 5 a OA. = Cry = Ct ~CH3. ” Lifer ee + 20. step lid deprotonation te farer_ether F —~— ee So : - fog oted Sty =(H3 == cyt, 0 CH CH 4 PRA? ils sorshay 2obilod yal + | Williamson's. cher k panes Se {| e-% Wea = gio. ReneNOTE: | re Bali! |. B2 ay Sysop ae nce ery ate eR EASES nt | possible te give cuch produces Lecrus4is yndlery oe, mere num ber of des results | are hot SN machonigsmi This is Lenuse alkyl groups present in alky thal [skeie kindsonc nd! alkoxid@ (0hs easily able to otinck such alkyl halides. Tharchore valky x ides shauing ph ov 3° alkyl gyourS- “have to be taken 4s Porm ethers having 2°01 6° alley | groups. f Mine is 2° or 3° alley! halide veackng 24 yni nadins with allexide sion, ib results im SMPs antec keto See cH port = C= Be 30 Now bap 2° and Fey halid des_undergo ce, Peatnis ise eb ecan, kor [db 2sd ° Strong bos es | bd they don't ock os nucleo phils here. | oH— 2 Edis do hob, howe buydwq en Lends woittrin ethers hove. o.ne+ dipole —AULMSselves , So +trory boil! ng pai nts ore significantly lovser moment => wea kly pol Chemical Reactions of ethers jp Pemetions Involving cleavage 2f6-o.bond We => Hydro. Uy Sis +=? Reaction with nuyjdrogen halide CHA) => Reaction with P Ole toe a logenation ~Electophilic substtuton. Reachow — => Witration ea friedalcrn f4s alkylation and acylation Reacti ons involving cleavage of ¢-o bend 5. bt Oy = + WYDROLYSIS +a : d/o pee ph eenaON eS PO => Ro OH + R-OnNCR PSR Dia Rtctach eixy i so ROH te Rak it dd OH + CH 1 » Methan o | Meltust ledide Step G): Protonation of ether ra ye - CH3-0- U3 + Sp =~ CHa = OSC oT ipa ina fees nat eee & v xii 26 ep Gil: Nucleophilic attack of halide ion prtonated ethey —__ Protonated ether LfMechanism Step (i): Protonation of ether See es tt eo — ———}__€twer Pootonated ether ——Step_Uid:Nuctephilic attack of Halide ion on protonated Pp pe: ether OR eee ae 3 L Ss = : #85 HEH = City + eos. <=) cht + CH, Cr, OH a x aS 2 ace ° ethers cw Sa eee wae treet tae > C3 = ¢ = - Cra-0b4 (sn) cHtg : eae, { 2k MeHronol Mechanism 1 ae 4 a. —__|| Step id ——_— — | are Pa TO z 4 Uta = © — 0 =. tH a}_thor FT bt Ong7 Gy = 0 sts + T I cn Stat — E “S a {1 ne, Prptonated: efhey i io ee ed ae We fen on penal _ ener = = S aero ‘Saeaeee i saeciee df ose' H20 solven eet __ tH. : +) Te Mere Oir (Wa = Tk CS = CH =O | ieee? 4 ca Anigple —_. Phen | — methyl ledide ;CTION WITH PC cg demotion R= Cl + R'= c1 + Pocky eee ie tomer li a so aitiwedasm 5 2H tl + POs 4 ylchlovideSS NITRIA TON sexo fee Whe. Hy S0y, enc: HNO3 nee HNOg | Anisole Si ere ec Ss af S | |} €Riepar cRAETS ALKYL ATION = | \ Oth, ie eal Orr anivydrous ALAR | a tows so aa _____o-allsyl anisole .-p (Q-methoxy toluene) (4-methoxytolvene | __+ | PRIEDAL craet's ACYLATION _ i ots, OCs Outs ree inne Alla I 2- methoxy. _ acetophenone __atetophenoné