y & Basicity of Organic Compounds ACIDITY Section - 1 Note : Note According to the definition of Arshenius, acids are compounds that yield hydro, yield hydroxide ions, OH. sn ions, H*, in solution while bases Bronsted defined acids as substances that would give up protons, i.e. proton donors, while bases were proton acceptors, Lewis defined acids as molecules or ions capable of coordinating with unshared electron pair (lone pair), and bases as molecules or ions which have such unshared electton pairs available for coordination, Organic Compounds as Acid : The strength of an acid, HA, in water. ic. the extent to which il is dissociated may be determined by considering the equilibrium, HA+H,O—==H,0"+ An _ HROMIAT] pa conjugate base (HA ‘The equilibrium constant, K,, is ealled acidity constant or dissociated constant of acid, ‘The value of K, serve as a useful guide to comparative acid strength, Acidic strength of acid « K, 1 pK, ‘The smaller the numerical value of pK, of an acid, the stronger will he the corresponding acid, ‘Strong acids generally b ave pK, values around 0, and weak acids, such as most organic acids, have pK, values that fare greater than 4, Weaker acids have larger values of pK, Very weak acids, those with pK, greater than =16 will not be detectable as acids at all in water, as the concentration of H,0* ions : [H,0°], they will produce therein will be less than that produced by the autolysis of water itself. Their sured in water at all. When acids are sufficiently strong, they will all be essen- tially folly ionised in water, and will thus all appear to be of the same strength, e.g. HCI, HNO,, HCIO,, This is known as the Levelling Billect of water, relative acidities thus cannot be ‘The following factors may influence the acidity of an organic compound, HA. 1, The strength of the HA bond 2. The electronegativity of A 3. Factors stabilizing A~ compared with HA ‘The stronger an acid, the weaker its conjugate base. The weaker an acid, the stronger its cojugate base. > > > An acid will donate a proton to the conjugate base of any weaker acid. > Anacid-base reaction favour the weaker acid > The stability of the conjugate base is a good guide (o acidity, More stable anions tend (o be weaker bases, and their conjugate acids tend to be stronger acids Self study Course for MJEE with One Suppor 1Acidity &Basicity 1 Acidic strength of acid (HA) oe Basie strength of conjugate base (A7) Basic strength of conjugate base = Negative charge density of conjugate base 1 Size of atom bearing negative charge 1 Blectronegativity of atom bearing negative charge Negative charge density of conjugate base ~ Strength of Blectron Releasing Group (ERG) < Number of FRG wo Strength of Blectron Withdrawing Group (EWG) ot No. of EWG 1 ~ Extent of delocalization of negative charge through resonance > Iinwamolecular H-bond in acid decrease acidic strength while intramolecular TI-bond in conjugate base increase acidic strength, > Presence of ERG (+1, +t) decrease acidic strength while presence of EWG (-I, -) increase acidic strength of organic acid, floy 1 ' (A) Hydrocarbon acid | TCH} GH + ca ~ Hydrocarbon Carbanion vei conjuste bse Relative acidic strength of hydrocarbon acid depends upon stability of conjugate base carbanion. Acidic strength of hydrocarbon = Stability of carbanion formed Stability of carbanion = Blectronegativity of carbon atom = Extent of delocalization of negative charge so Number and strength of WGs © No. and strength of ERGs For Examples : 0 CH, CH, < CH, = CH, < HC= CH (order of acidic strength) pk, 50 a 25 Because carbanion of HC =CH is more stable due to high electronevativily of triply bonded carbon atom (sp hybridized), 2 self study Course or IEE with One SupporRicca nace (i) iy aw ” wi) F,C-H < C1,C-H (order of acidic strength) Pk, 28 135 Conjugate base of chloroform is more stable because of greater delocalization of negativ tharge via back bonding (p*- OHC-CH, ~COCH, > HyCCO-CH 0K, 50 58 89 ‘OCH, CHO js stronger EWG than ~COCHY hence greater stabilization of conjugate base. Ovder of acidic suength: CH, Me—COOH > Me-CH-COOH > Me-C-COol 1 Me More Number of ERC Ky 37 ar 48. 5a IF there is a doubly or iiply bonded carbon atom adjacent to the carboxylic group carbon then acidic strength i increased, CH, -CH, -COOH < CH, ‘This is due to the fact that the unsaturated o-cacbon atom is sp? or sp hybridized, which means that sp? or sp hybridized carbon atoms are less electron-donating due to their more electronegativity compared to H-COOH < HC=C-COOH sp" hybridized carbon atom. Set Study Course for ITJEE with Olive Supportty ty II. Substituted Aliphatic Carboxylic Acids : Presence of I'W inerease the acidic strength of carboxylic acid because it decrease the negative charge density of conjugate base by electron withdrawing inductive effect of substituent, F)WO stabilises the ‘carboxylate anion and incresse strength of the acid. I. 9 a a rete ph I O-n I oF [Zs an electron withdrawing group (PWO)] ‘The introduction of WG further away from the carboxyl group than the adjacent o-position, has much less influence. Its inductive effect quickly dies away with increase in distance from carboxylic group. “The effect ofthe following groups in increasing acidic order is Ph CH,-cH=c. This is because of greater clectronepativily of sp" hybridised carbon to which carboxylic carbon is attached. CH,=CH-COOH —CH,~CH,-COOH C= c-coon (ok. = 425) (pk, 488) (oky = 184) wo F,CCOOH > C1,CCOOH > Cl,CHCOOH > 0,NCH, COOH > NC-CH,COOH> F-CH,CooH> Pk, 02 064 1.25 1.68 25 258 CICH, COOH > BrCH,COOH > HCOOH > CICH,CH,COOH> C,1,COOH> CH,COOH> C,1,COoH 2.86 290 377 450 4.20 476 49 Il, Aromatic Carboxylic Acids : Aromatic carboxylic acids are generally more acidic than saturated aliphatic carboxylic acid because phenyl group is less electron donating compared with alkyl group. ° ° A A O-< RCH, eS o-n o-n tron Donating fect of More Cectron Donating ec of env group, more a strength yuo, les ee strength P)-COOH cu, coon (0m 420) (ok =476) Leselecvondonsting Noatearon orestetion treceiehgeup.* —donatingetec stato donating’ Substituted Benzoic Acid > For comparison of relative acidie strength of substituted benzoic acid use “ORTHO PPVECT™ Ortho effect : It is common observation that generally or{ho substituted benzoic acid 1s more acidic than its isomeric meta and para substituted benzoic acid even more acidic than benzoic acid itself. This effect is rvespective of the polar nature (EWG of ERG) of the ovtio- substituent. coon coon AZ «< (Order of aie strength) Z coon coon coon z and < lorder of acide streneth Zz Zz (2= ERG or EW) 6 Self study Cours for TEE with Online SupportRic Cucumis Acidity & Basicity Osho effect is a cumulative effect of various acidic strength enhancing factors such as steric inhibition of resonance, strong inductive effect from nearest position, intramolecular hy. bonding in conjugate base ete OS OS HON An ortho-substituent tends to prevent this coplavsrity because of sicric hinderance, Thus, resonance is prevented and there is no +R effect of Ph-group. This result in more stability of conjugate base duc to less negative charge density and hence greater acidic strength. It can be said that greater the s(cric inhibition of cesonance, the stronger is the acid. For example order of acidic strength of ortho substituted benzoic acids is as given coon cooH coon “Cy Cr Come), Oo ox, 321 3.46 3a. o-Hydroxy benzoic acid (salicylic acid) is far stronger than the corresponding meta and para Stetic inhibition of resonance can not explain this very large increase, sinc methoxy benzoic acids all have almost similar strengths. corresponding coon coon ‘coon OMe ‘OMe OMe mK, 4.09 4.09 4a7 Very large increase in acidic strength of o-hydtoxy benzoic acid is explained by considering snleamoleculas ll-bonding (ehelation) in conjugate base carboxylate ion of a-bydroxy benzoic acid. Conjugate base is stabilized by in\ramolecvlar hydrogen bonding while such hydrogen bonding is, not feasible in o-methoxy benzoic acid and iti further supported by the following order of acidic strength. set Study Court for IEE with Online Support 7Acidity & Basicity RUC GGUS creed ‘coon coon Coon Oo oOo" “co °K, 420 2.98 On. 0 8 ie Or 8 O or (ocblsor Leestabls)—(Lesecossoo) (More Mar stab) Intramolecular H-bonding Nointramoleculr H-bonding more stable less tle > Comparison of Ac ic Strength of m- and p-isomers (0) The introduction of alkyl groups into the benzene nucleus has very Little effect on the strength of oO C. (li) The introduction of electron withdrawing groups (-R effect) increase the strength of benzoic acid, ‘more increase in acidic strength when they are in the o- and p-positions. Son Ce coon O Oo ao oO ~ (+1 Effect} [More -1 Effect] [ R & -1 Effect] [Ortho Effect] Self Study Course for IITJEE with Online SupportNi uum Acidity & Basicity (sli) The presence of group such as OH, OMe, halogen having an clecison-withdrawing inductive effect, but an clccivon-donating mesomeric when in the o- and p-positions, may cause p-substituted acids to be weaker than the unsubstituted acid itself. e.g. p-hydroxy benzoic acid coon coon coon coon cl cl a pk, 4.20 3.83 3.99 294 [Effect] [Dominating ~1 effect] [Ortho Effect] ote: -Leffect of halogen dominate over their +R effect. coon COOH COOH CooH OMe ‘OMe OMe pK, 420 498 4a7 409 (Hetfect] (effect) [8 & 1 Effect] coon coon coon coon ou ‘OH ou PK, 4.20 4.08 458 2.98 [effect] [eR Effect] [Ortho Effect] WV. Dicarboxylic acid As the carboxyl group itself has an clectron withdrawing inductive effect, the presence of a second such group in an acid might make it stronger, as shown by following examples “ HCOOH coon w CH,-COOH CH, -CooH | | cooH cooH Kaa? 12a Px, 476 2.83 [1 etfect} (st effect) [-t effect] ai CH,-CH,COOH CH; CH, COOH | cooH mK 438 439 [st effect} [effect Self study Course for IJEE with One Support 9Acidity &Basity COOH 000K CH, -COoH 6) 1 cn, 1 coon ™~cooH CH, -Coon ek, 123 283 a9 [Stronger -1 Effect) [Weaker =I Effect) COOH COOH coon COOH o OU ee ‘COOL ‘COIL coon ek, 4a7 2.98 3.46 ast {Ortho Effect] HEtfect} [Weaker Ffec] HA foot Hooc™ Mt Phy, =192 Phy, =3.02 tnrmoeclr toning No raat H-bonding inconiueate base mating ‘ncoriugete base masing imare sible & ai more songs Tes able & ad weaker 498) occurs more readily than that of the cis-scid Note The second dissociation of trans-butenedioie acid (0, 6.23), because of the greater difficulty in removing a proton (H-bonded) from the negatively charged eyelic system derived from cis-butenedioic acid 9 oO b 1 Wy A088 A C, 8 Kongo i / I WO Nc—O HOLA, I i 6 é - {intramolecular H-bond} {No intramolecular H-bond) Second dissociation constant of saturated dicarboxylic acid is weaker than their corresponding saturated monocarboxylic acid. This is because the second proton has to be removed from a negatively charged species containing an electron-donating substituent ic. COZ which destabilize conjugate base more. 6,c—cH, — More neste charge Lestneatie charge ety kerb sent ore sabe » Self study Course for TEE with Online SupportNie ceu ace Order of second dissociation constant (c) HCOOH > coon I coon (ox,=37) (ox, = 4.2) C00 > ‘COOH > CH, -coon 1 fp - COOH, (0K, = 4.88) (0K, =5.6) Phenols : Phenol is weaker acid because its conjugate base is stabilized by delocalization of negative charge but extent of delocalization is less due to non-equivalent less stable contributing structure. Phenol is weaker acid than carboxylic acid because in carboxylic acid, conjugate base is more stabilized due to formation of equivalent contributing structure during delocalization of charge. cater extent of delocalization ‘due to equivalent contributing structures CH;-COOH ~— Ph-oH ~—Ph-COOHT Pk, 498 9.95 4.20 Substituted Phenol: increase acidic strength of phenol while presence of G decrease acidic strength of Presence of 1) phenols. In the case of a nitro substituent, the inductive effect would be expected to decrease with distance on going 0- m-—> p-nitrophenol but there would also be an electron withdrawing nicsoneric effect when the nitro group is in the o- or p-, but notin the m-position, and this would increase acidic strength of nitrophenols because of more resonance stabilisation of their conjugate base setfstuy Course for IEE with One Support _ TEE 1Acidity & Basicity RUC Gucur one oo" a @ ok, 9.95 8.35 744 ~1 effect ~ Wand “1 Effect Order of acidic strength ‘Note: Introduction of further NO, groups promotes acidity markedly, on ou on NO, ON. No, w No, NO, Pieric acid ok, 9.95 401 1.02 Most stable conjugate base greater effect OH ou iy I. ON’ ‘NO, ON’ ‘NO, No, oN Lesser Electron Mare Electron withdrawing effect withdrawing effect Onder of acidic strength II>1 In) effect of NO, group at pars postion isnot possible because of soc inhibition oF vesonance while in (i) -& effect of CN group increases acidic strength. [steric inhibition of resonance is absent in this case because =CN is inear group] . » oOoa . ‘ ok, 9.95 20.28 20.08 1029 [i & effect) [41 effect} [iv effect) 2 Self study Cours for TEE with Online SupportWiener Acidity & Basicity ‘Order of acidic strength ve Xe . . ova ah w Me: Me « igth) “A &-effect of NO, group Only effect of NO, because of. Steric inhibition of resonance (D) Carbonic acid : ‘Cathonic avid is a weak acid and ionized to a small extent to bicarbonate ion. ‘Catbonic acid is weaker than carboxylic acid but stronger than both phenol and alcohols. 0 0 A 2 cH, eZ Ho -cZ C-o-n on ou 0 6 A A oH,-c no-c o <. < oO vn etcainon emission mi ce tesanaanon ohm nnn sorkans ie figup renege my Moet rg ey Som opens Order of asic strength Acetic aid > Cosbonic acid > Phenol Note: Among compounds containing carbon, hydrogen and oxygen, only carboxylic acids are stronger than carbonie acid ‘They dissolve in aqueous sodium bicarbonate with the evolution of carbon dioxide. This behaviour is the basis of a qualitative test for carboxylic acids. (CH;COOH + NaHCO; —> CHjCOONa + H,CO, ‘trong ald Weak ald HCO, —> 1,0+C0, 7 PROWL + NallCO, =< HON + COs Weak acid stuong acid > Bicarbonate (pK, = 10.2) is @ weaker acid than carboxylic acids but a stronger acid than water and alcohols, Self Study Course for IITJEE with Online SupportAcidity & Basicity RUC GGUS creed (E) — Sulphonic Acid : Alkane sulphonic acids (R - SO,OH) ate stronger acids than carboxylic acids because of grester stabilization of conjugate base of alkane sulphonic acid due to dispersion of negative charge over three oxygen atoms, © 2 ° 2 A Mec BY Me c= Mee on ° ” chug decd over onan som c y= Me 3—0 ° Charge delocalized ‘over 3 oxygen atom Presence of RCs decrease acidic strength of alkane sulphonic acids while presence of !°\V/Gs increase acidic strength of alkane sulphonic acid, q t Me-$-on on on,-€ Ys on Of on (ye 1 * i ou é é Metamsdoboe Twuotmstiane phitvternenbhne—neesshone tne or ‘uote aa a ssa = 3 28 63 42 {F)_— Mercaptan (Thioalcohol) : ‘Thioalcohols are fairly acidic with a pK, around 10 - 11. This is because negative charge is spread over larger size sulphur atom, eon #5 Meo™ 185 More negative charge density, mare basic MesH —#"_, Mes~ °K, 10 Less negative charge density, less basic ‘Note : The solubility properties of acids and their salts may be used to remove non acidic impurities. A carboxylic acid is more soluble inthe organic phase, but its saltis more soluble in the aqueous phase. Acid-base extraction can move the acid from. the organic phase into the aqueous phase and back into the organic phase, leaving impurities behind. EME organic impurities ‘cid & Organ Suse ay aca ste wih tmpurttes | war no" heater che ois at [wt inorganic nour is L_Wier purities Mixture aed» mourn) FY Sel study Cours or HEE with Online SupportNi uum Acidity & Basicity BASICITY Section - 2 Organic Compound as Base : Nitrogen containing organic compounds having upshared electron pair on nitrogen atom acts as organic base ‘The strength ofa base i, in water, may be determined by considering the equilibrium. Hon == Bh” + OF Base Conjugate acié| (1) (1) ‘Tae equilibrium constant in watt, K, is given by Ky =F Strength of base = K, 1 PK, ‘The strength of ase is can also be described in terms of K, and pK, of conjugate acid, 811” of ase (B101,0%) pit) =11,0 = B= H,0 a S oe? [BE] Strength of conjugate acid BAT = Ky 1 PK, 1 Strength of base 8 =~ strength of conjugate acid (BH®) ‘The “stronger” B11” is as an acid, the “weaker” 1) will be as a base. ‘Thus the smaller the numerical value of pK for 11" the weaker |i is asa base. oie. K,xK,=K, orpK, + pK,=14 Strength of base = pKay.. > Strength of organic base depends upon availability of unshared electron pair on basic site > Availability of unshared electron pair on basic site increases due to presence of electron releasing group and it decreases due to presence of electron withdrawing group. > Availability of unshared electron pair decreases due to delocalization of unshared elec\son pair through tsoane silat allowing evans unstared pair ‘dustosleczon ‘stharowing fer ltt of unshared © gle ‘due to electron co scth sch, CHy-NH, CSP H-NH, “i> CF,—NU, Selfstuy Course for IDEE with Ontne Support TTT 15Acidity & Bascty CH,-CH,-NE, CH CAN, — CH, C~ Ri wn we sates, satan localized deloclaee Further, strength of organic base also depends upon stability of its conjugate acid (BH®) 1 Stability of conjugate acid Positive charge density of conjugate acid 4 s _ Extentof solvation of conjugate acid Extent of delocalization of positive charge of conjugate acid Number ofERGs s< Strength of ERG Number of EWG: 1 ‘Strength of EWGs | Aliphatic Base : (Aliphatic Amine] ‘The strength in nitrogenous bases is related to the availability of the unshated electron pair on nitrogen. This availability of electron pair increases due tothe incressing inéctive elect of alkyl groups in aliphatic amines. NH, Me-NH, Me-NH-Me Et-NH, Tt-NH-Et 20.87 20.98 ‘The introduction of an aly! g:0up into ammonia incseases the basic strength markedly as expected. The introduction of a second alkyl group further increases the basic strength, but the net effect of introducing the secon allyl _svop is Very much less parked than With the first, Ibis due to crowding around nitrogen atom because crowding decreases readiness with which a basic site take up protons, ‘The introduction of a third alkyl group actually decreases the basic strength, Me 1 Me-NH-Me Me—N-Me [Decrease in basic strength] Phy 1077 980 Et I Et-NU-Et HL-N-Et [Decrease in hasie strength] re Self study Cours or IEE with Online SupportNiece ace ‘This is due to the fact that the basic strength of an amine in water is determined by ©) Blectron availability on the nitrogen atom, also by ‘The extent to which the cation (conjugate acid, BH®) can undergo solvation, and so become stabilized 1a. o 1a. => Teroalkylammonium hydroxide (RyN® OH®) yield basic solutions comparable in strength with the miners! R,N°OH® —>R,N® + OH® R,NH® +0H® R,N+H,0 Self study Course or MAEE with One Suppor ”Acidity & Basicity Pee Order of basie strength ° ° ° i & L Lo ¢. ~ \ \ Nib > NH NH SOB w |x o D HO CZ C i i No ° ° More table conga base k,=830 > In some eases ‘clocalsstion of unshared electeon pair increase basic sceneth of amines as seen in pvsnivline, HN = C(NIH)3 . Guanidine is one of the strongest organic nitrogenous bases known, Its because its conjugate ° acid (BH®), HN =C(NH3), is stabilized by delocalization of positive charge symmetrically due to the {ormation of three exactly cov alen\ contibuting structures. Note: A somewhat analogous situation occurs with the »miclines, R - C -NHp 1 NH MeCHLMH, Ctl, C-Nily H,N- CNH NH NH he 1m na 26 I. Aromatic Bases : Generally aromatic bases are weaker than aliphatic bases or ammonia, Ome Om , ailing Cyelohery! amine Phy 925 10.68 In aniline the nitrogen atom is bonded to an sp? hybridised carbon atom but, more significantly the unshared electron pair ‘on nitogen can participate in delocalization through resonance. Hence there is less availability of electron pair for protonation. ot O-O-O-0 . Om Ove Resonance stabization No Resonance stalirtion high postive charge densty less sable, more acice 6 Self study Cours or IEE with Online SupportRi eeu ee Order of Basic Strength : @ ai) in) ww o o™- oO” Pha 1088 wm Few ae te I Oo" - O™ - O™ Unshared electron pair hy, 482 aa sas ‘This small inerease in basic strength with introduction of alkyl eg. Me group on to the nitrogen atom of aniline, suggest that cation stabilisation through H-bonded solvation [responsible forthe irregular behaviour of aliphatic ‘amine] has less influence on the overall effect. The major determinant of basic strength in alkyl-substituted nilines remains mesomeric stabilisation ofthe aniline molecule [mote stabilized by resonance] with respect to the ao Oo co a ¥ v. . “+ and +1 effect of Me but less +leffect of Me “Heffect of Me wh es we vps Sterichindrance Note: The exiss base weakening effect, whem the substituent isin the o-position is due in part to the short distance over which its inductive effect is operating, and also to direct interaction, both siric and by hydrogen bonding, with the -NH, group, Self study Course for MEE wih Onne Support TTT 15Acidity & Basicity COMI cecrs NH, NH, NH, NO, NO, ON. NO, wi NO, No, ‘Such aweak base that Very weak base insoluble Extremely weak base, it resemble Its salts are largely hydrolysed In aqueous acid an amide, Its called pcrainie and readily In aqueous solution ‘undergoes hydrolysis to pierc acid NH, on ON. NO, ON, NO, on ——> + NH, No, No, Pietie acid HL UH Me. Me ON. NO, ON. NO, i No, No, 0 ™ Powert election Novelocl sation of Lone pa electron withdrawing neso-eric Ining and ~> base weakening 5y ‘rec of NO, groups mesomeri electron wiherawing efect of No, because of eb ion of ezonanes [Y]is about £0,000 times stronger a base than that [X] NH, NH, NH, NH, OH willy ‘OH on “elect st efiect -nelect “etic ess stabilization of, ‘conjugate acid by soNation aa 530 ha, 462 an 20 Self study Cours for THEE with Online SupportVidyamandir Classes Order of Basic Strength : Acidity & Basicity oO” on % won sa, say wo (ix) Order of Basic Strengtt O on a ; R . Lone pairon so" Natom Lone pairon so" Natom Lone pair on sp N ator ‘Order of basic strength observed is as follows. R RL Re ‘This is due to the fact that as the nitrogen stom becomes progressively more multiple bonded, its lone pair of electrons is accommodated in an orbital that has progressively more s-character, The electron pair is thus drawn closer to the nisoeen ‘nucleus, and held more tightly by it. Thereby becoming less available for forming a bond with a proton, with decline inthe ' R-N-R > C=NH > R-C=N basicity of the compound. Heterocyclic Bases : < ft ® CO i Be Lone pair on sp’ Natom Me-C= Lone pairon so’ Natom Lone pair on sp Natom selfstudy Cou for IZEE wih Ontne Support _ TTT Ty 2Acidity & Basicity Order of Basic Strength : Lone pair on sp’ Natom Phage 1088 Order of Basic Strength : Q Quinucisine Delocaized Lone pair electron PK -on Order of Basic Strength Lone pair on sp’ Natom 4 (| NY Pyricine OO 1 H Proline Localized Lone pair electron (iv) Most Non-basic (pyrrole = like) nitrogen have three single bonds, and most basie (pyridine-Lihe) nitrogen have a double bond in the ring. asclocalzed \ < mI XQ Not base delocalized _ fone pair H 2 0 0 O H H Delocalzed Localvedtone pale locslvedlone pair Loca! 7ed lone pair sp! N atom lone pai sp" Natom sp’ Natom ‘effect of 0" atom oh 027 sa naz 93 Order of Basic Strength : -O-O- 86 Purification and Separation of Amines : Protonation of an amine gives an amine salt. These salt are ionic, high melting, non-volatile solids. They are much more soluble in water than the parent amines, and they are only slightly soluble in nonpolar organic solvents. Formation of amine 1 H salts can be used to isolate and characterize amines. Most amines containing more than six carbon atoms are relatively insoluble in water In dilute aqueous acid, these amines form their corresponding ammonium salts, and they dissolve Formation of a soluble salt is one of the characteristic functional group tests for amines. a, aN Suc! ot tree amine 2 pr sat waterinae irersouble ‘The formation of amine salts can be used for purification of amine. The amine is initially more soluble in ether than in water. Addition of dilute HCI converts it to the water soluble hydrochloride salt, Neutralization with NaOH regenerate the free amine. The formation of amine salts is also used to separate amines from less basic compounds, fer EME» organic impurities EE 5 ne & Organic, Stet Sey mine ‘Amines —Ssewith_| impures Fe Lye sone sat Aimourites “heer Wate " [wer Inorganic np sities L__water y Impurties adsaks Self study Course for DEE wih Onna Support ATT TTT 25