Alcohol Phenol And Ethers, Lecture notes of Chemistry

Download Alcohol Phenol And Ethers and more Lecture notes Chemistry in PDF only on Docsity! “Alcohols and Phenols :- when a hydvo gen of abibhalic oy avomahe Wydrocarbons 1 yeplaced* by (-OK) grup then the compoundo twhith are obtained aye called alcohols @nd phenols. Ry —Ot 4 Ror Aliphahe Ky dyocawbons f(Cohol OH OH CSS SER eenens Aromaht Pupdyocaybon Phenol ter Also called Hydwxy derivatives of Hydsocarbons. Classification of Alcohol and Phenols On the basis of wo- of -OH groups [ J 1 Monohyd vic Diluy chic ‘pulp hyde CHy OH CH, OH CH, OH i rig OH aa OH ov i ani po pk H we Xb pm i> NG +H Hc KEN Y 7 O7 al \0 9° {°° Wot The C-O bond \engm tn phenol is 136 Pm wohtey, Less than alcohol due to (4) I phenol , Lone pais 4 oxy gen a conjugation twwtth if bond of arom at ng sig Qnd acguixe paral dowbole bond Cnaxsauery: UL) Th phenol Oxy Gen alam ‘vo aHathed to sp? hwbondtsed carbon. freparation Of Alcohols: - From Alkenes: (By Hydvaton of Alkene HT CHy-CH=CH, + H-O-H OH | CH, _CK- CH, Propane t-ol when alkene seach with water im the ovesence of arid catalysed , then alcohol io fxmed Ov un symmebicol alkene, Lohen Wares molecule vo added, then product vy foxmed acco saling to Marxkovwkovic Rule. Ye Mecho nism: HO + HT ——+ 4,0* Ht H / [ “CE=C6 ~ Peg = 1b 14% + HO Ger? 4 oN Hy # 46-07 . [ ( +HO —s 4020-6 py + Cee ®> a \ Aan HOt ay ~ic-O 4 4+ HO 7 TCT { ; qj. By Hydroboraton- Oxidakon_ 3 (CHg-CH =CH,) + LByH, —> (CHy CH, CHL), 8 OH™ + Sty 0 (Ch, CHy-C(H-oW) 8 ct + (OH), Lohey alkene seack xt diboxane ( B,H,), then trialky! bowane is foximed which gives alcohol wy the oxidation of HyOy m the presence 4 sodium dda xide Fyrom Carboy! Compound: ‘By the veduction of aldehyde and keto ec Aldehyde and Kelohes are veduced t the coxresponding alcotde by hydrogen mM the presence of reagent Ltke pt, Pd, Ni, UATHy , NaBHy ek. { In the presence of Pt/fd we take Hy 4 west 4 these take 2H) + Pd Al ae T Hy +> R CH, - OH 4° alcohol bf -CH- A CR TH, —_Y R . R 7 alcahe!, 0 H >From the reducton of Casboxylic acid & ectey > e-c-on +4n7 MMe 5 RCH OW +HO o Carboxylic Aid Alcohol Rec s0-0 + GCH] GME. - CH,-OH +R- OH 4 o estes. -From Grignard Reagent : “when gxignard teagent xeack with aldryde ahd Ketone rthen alcohol i formed Q >c=0 + RM-K —> >= Oryx | R Adduct \C-0H + Malon) x Hh lo H d H,© a dt yrc=© + R-Mle-K —> H-CH 0 AO, H— (HOH Mp oy am p Ho 4 cy -OH + My # Px cog + RMX —> Ret -O ——> R CH oH Ro mx Reali) a Ketones give 5 atohe| 7X “Ou RK \ H-0H edc-OH 4 Mi C20 + R-MeX —? eet Tr ie” f tr Solubility : | > Sq uy fj fy of akgwos and bhenls m way is Ae to the, aby ty to form Hig yvogy Bonds uf watey mg e cule, + TM shetty a ecvences with ‘nese m Se 4 Qky | asy ¢ Wyden ole ) Gxoube O-H-20- H-~*PTH e-O-H 1 ( Q H a =) 4 Aut whig geavage of -O+H bad Fakes place 2 4 Mm which qeqage —CLOH boy takes by te # Raw in which cleavage of —O-H bond tekes place 17 ae Dg? ahagy > F akon L) Acidic Nature of Alcohol and Pheno| — a) Rxh wilh M ar tat Alcohols and phenole veack with achve metale , uch a0 podium, potassium and aluminium to yield comesponding alkorides/ phenoxides and hydyogen. ARO-H +QNa —>* &2&0-No 4H, OH Sodium alkox ‘de CJ 5 Na —- ~ ane ors O +H, Phen | Sodium bhenoxide OH Ova CO 4+ NadH ~—_—+ CO + H,0 codium phe noxide | The acidic nature of, alcohol ta due ty the polay nature 4, -OH bend. p In altohel an e° veleasing gyoub (—CH, 9 - He) Increase the e@ density on oxygen atom and decrease the bolayity 4 “OR bond. Dug tm dil the acid Steen 4 alcohol algo dehease Ther ¢ bye, the order q acidity 4, ditterent altond {4 ac. Rn R>+CH,-O# > Rs ct otf > ROT Or ‘ a Q.why alcohols are weak acid than compart to water ? fv» In alCohol, alkoxide ion iS fowmed attey Removing Ht ion and im oak Wydvoxide fon 's formed abter semovivg Ht joy, But alkoxide ion ic Qess stable than tombare th on” ion due te the peesence 4 more €© density on oxygen atom. Therefore alcohsl act ao week acid than Compare to waly, | R-O04H ——> RO +H" Alkoxide fon(lece steble ) henol Phenol to Ynoxe acidic m natu xe than towbar to alcohol. Reason: ty {onisahon 4, alcohol and phenol takes place as— R-OH R-P +t Alkoxide jon pH 0° wo ——. Cc + Ht Due to the Wiphe x € lec hronega tivity 4, Sb* hybvidiged cavon d phad to whith -OH ‘yp attached, €° de Nig ty ce traseson aygen. The (ny ase tre pdanty of OH pnd ad xesult man {ncreae fuionisatyy of bhendo that dat 4 alcolols. ™ alehd alle xde (on is formed art Im Mad, phnonck jov able semmung tt io .Phen y'de : g LOW 18 ore stah#e cle to yesomwe “ton compare tn alkoxihe in. Thexé fpxe ple wl ‘o nore acdc than akohd. @ Exh an the Fal owing obser vakm - O- and b- Ntwopads ave move Gide man end. NOp being Gi A@ hon ui Hd xawing group whe present at oxtho and fnra-foshion wi th draws C& dew ity tm bewhe ing Heeby dew easing the ce okmity 4 OH bad and “thus woke the x eleace 4 prvton & ger IN at 40 —> L + 0" 4 LO No He O=C ENG qprimpnml Pt, Lae? eK sy ute (7 YO | O-nthopphend Also, the -NQy gyoup inensibien the eve chahge q phenoxide ion and Hus, stabilise 1t and hence {ncrease i ecrolec 74 : Om Apength as. & ¢ cy" ¢ g a Hene orth) and pon rubophenl axe more Acidic Han phere hydvahon 4 Harel in Hhe presence qd cone H, S04 oe the aseurigmeaia steps: et St | a) k - —6-H +H* fe - Ha -c7- OR H Ww Proton aded Ghote igi Cetatl eran i 8 . 2 8 4 H Hoy q H-e on Sh -Ly Siow Hc - Ctr + H,0 roo TT J, u H , Mea Cl 4Ht hee =P wo Etnent. ~ oxidation “| alkohol (nvolve the foxmation q. covoon - Oxygen bond voith Cleavage q an! O-H H ' bord and ‘C-n’ bond. REC OV ——F CFO TH, > Ws process y also Known a Aemydwogenahon Pamayy Alcohol > It is oxidised into aldehyde whith fs d uxiher oniotted int) @n Q@ctd. 2 fo} , CHy- CH-0H 24 Chy-CHO CH,-GOOu “io p Ald che de Acad. Tt i¢ oxiclised info Ketone colich yp 4 uvthey oxidised into acid CH; et “cH on +60) EES ceo CH, ed CH, Plo) CH, COOH + HCOOH Tt va not oxidised in ovdi nary condition but im the Presence oO Shong oxidising Qgent, Q qniktuhe q cayoo cyfiic aud if fosimed. + Pehydrogenation : CH,- CH, - OH At CH,- CHO +H Nor OH —t+ “hco +h, ttt My CH In case 4 3° hy Gy I” |adtonol, deky- Ch-C-OH Bp? “SH | ah sake $y CH Place. CH, 3 Rx" due fo -OH group of phenol -ReY colth flmmova | NEY OH fry of Zn OH A (o) +2" =» () m0 Phenol Renvene OH tp (of + eels ToT + POU, +e Rx"_due_to benzene ring of phenol Resonance mm phenol O—H H—Os ad oey “Ee (1) (II) a As a yesult o resonance , bebe us wat Ren takes plate at pxstho and para position Te : dil. HNO, er 4 9 -Niho AP TBEK pheno] O 6 -Nihophenol a 2 op OF Cone HNG, ia NO, [ —————-> 0 ¢, 4, 6 - Tyintho phene| Chicric Aud ) NO, Compound CH,O0CH, C,H,0C,H; CH,OCH,CH,CH, C,H;OCH, a 1,0CH 1,C] Ly C,H; O(CH,),- CH, CH,O—CH —CH, CH, Ci, -O— CH, CH,— CH—CH, CH, CH,- O - CH,- CH, - OCH, H.C. CH, cy" Common name Dimethyl ether Diethyl ether Methyl n-propyl ether Methyl phenyl ether (Anisole) Ethyl phenyl ether (Phenetole) Hepty! phenyl ether Methyl isopropyl ether Phenyl tsopentyl ether The bond angle POR re Game st ar el a Methoxymethane Ethoxyethane 1-Methoxypropane Methoxybenzene (Anisole) Ethoxybenzene 1-Phenoxyheptane 2-Methoxypropane 3- Methylbutoxybenzene 1,2-Dimethoxyethane 2-Ethoxy- -1,1-dimethylcyclohexane bw (C7 °X¢) vo 444’ due to vebulcion between alkyl gyoubs, wohich axe attached to oxygen ahwm igi pm L O CHg —S CH, iW" Preparation of Ethers ‘By depydyahon of altohol Hy Soy dr lereor Mechanism — . The foxmastion of etter n Suz involving the aHacR 4 allconol molecule on a Pbrotonalted atoll, 4 (8 CH3- CH, -O-H + Ht — > CH CH, > OB. H (ti) CH, CH, - O° + CH, “chor link (Hy CH, - © ~ CH - i An an + tT H,O (tit) CHy ~ CH, Orb trh — CH, (H,- 0-CH CH, tHt H ushen Aodium ex potassium alkoxide axe healed with alkyl halide, Hen ether is fosrned, Fakes place by Sue mechanicn R-X + R’-O0-Na — > R- 6-R' + NAX. Chr Hy Ch - c- O- Nat +(K,-Bs —> City o- dt, + Naby CHy Hy In case qd 24° and 2° alkyl halides, eliminaifou combletec Overy substtulon. If a 2° alkyl halide 1s used an alkene to the only yeacton pavduct and no ether is foarme Bis CH,- CA By t+ Na'- 6 - ~CH, ——> CHy- C= = CH, + NaBy +4, 0H CH, cs J-MeHuy! propane Phenols ave also converted to ethers by this methed. b° Nat © Ch CH () ¢ CH) -CH-Br af ai ¢- Naby god. Phenoxide Ethoxy benrene Tpim 4hyl ether and d ety! ahev ave g geows an dother then ave Uqud m wature . ) thers ave UGhtey than water ie dee fy y Les man w ater: d ‘)éthes ave fughly yo bh’ @ wm nature. +) GGAlUBELIAP ¢ y, es are parhally cdubem water and ave Wonly bible m bhdroform aod Ce ac. ) Borking Print orking Fr the b oF ethe x is vew ss tha u Owh ore to | Dimer é ale ad because m ether Nlesmdealar H- nai vg ont present - Te buF d ether yy drmuloy t HL mek alr wt . 4 strane Chemical Properkés Hydwdysic GOe O-GHe THO oat & GH cOH HI pHRy > RU >? HE ff Reaction woth BES hey ethey reack with HI vk fot ane cold medidm , then different Product v' formed SH he Her 2 GHs T + 1,0 Wir _G@ld | CHe OH + GHe T Gg -O “Ag Cty{ alcoho] &thy| idclide