lecture No + 4 ‘errc 1 + INTRODUCTION + Amines + Amineg ave the derivative of Gnmowa , obtained by Yeplacement of one of, tuo or three hydrogen. by alkyl /axyl grup. Aluphatic Ames + Amines in which alkyl gloup Yeplaca hydvogun Gem amend 18 Known ay Aliphatic Amines. oe R- NH (any —H + R ——> ANH ) AUK gl group) Aromeche Amines + Awines in which. aryl gloup replace lydiogen frou ammonia 18 Known a Ayomatc Amiues ° oy" (Nig —H + GHe ——> Gis Nia ) | Uy erayt) lopre 2+ ClAsstFIcatToN Dopeucliog upow the nomber of allyl or awl groups attached to the wutregen. atom » Aliphahe oY avowatic “Amines ove clossifeed oR Binary 19). Steondary G2) cand Tevhavy (3°) amines 3 the wwinber of H-atems attached to te NH atone is ty! then the degme of Aine = (3-H)? SN AMINE No OF H ATOMS Dearee FUNCTIONAL 4 ArigieD 12M (-n)® Grove E i a4 R-—N-H a £8 ox Prnwavy =NH H | 2 R—N-R 4 or Secondary =NH- ‘ : R-N—R ° 3° ov Tet =N 3 lev Mia 3 Nore —Armteenavun Slt (Ranttxé) ave different ftom Amines ) Scanned with CamScannerin] | Torre 3 + STRUCTURE / | * Nitrogen fom ef cnunee it favalent amd CMS AH Ondbeve Pay of Clectrong - 3 b ‘edi * hikes Auweue, tle Ni oxbitals qf omnes oe AP Aybridised 4) the geomehy of ominen i&- PyRAMTDAL (3 Bond fear, 1 lene pair ) 4 i 1s ast ape 2h Ae * the givud shte elechowe cenfigurecion of NV iB AS, 8px; Afar. ifere one 28 ard vce 2p (Pa,BysP2) aabitel hybricheny te fem oor 5p? hybridieed orbitals. theo of Mem have cue electron and form 3 bod pure aud fe Cre has cue (one parr « © Due to dhe preseuce % unshared par qf electron , the ‘boud augl 18 (egg than 109-5? , (C-N-€ where € = Cork), © Due to the Prescnce of lore parr of electrons cu nitvogen thy they (aa douale , Ce 7 hence we cou ay Anamee can act oy Nucleoplile, 9 N a 4,6 / Chy ye ( Pyramidal Shape of Fiivellyl Aranee ) Scanned with CamScannerLectuRE OX + foere + TuPAC NoMENCLATURE foy PRIMARY AMINES R-NHa Sofie Amine Frefx+ Amano TurAC NAME + AlKonamine —_(Allane -@ + amint ). Common NAME — AlkyLomine CompovnD Tupac Common NAME NAME Clig— CH2 — No, Ethanamine Sthy( Amine: Cty~ CH, —CHo-NH2, Propow -$- amine he Propylamine. oY fropanowine Clk - cf = ch, Prepa-2- audve Teo propylamine . Nib HOH CH Hy Ni Prop ~2-en-1-awine or Nie ONY (Pye) Nt — (Ctl, )p— NM, > Hexan- 1, 6-diawine Hera mie tlylenediqusine. LPys) YWreoe- Ni - But- 2-en~ J-aume (yg) Scanned with CamScanner+ for 2° pmane THEeoRy + | K- " —R | | kab roof a) H l, More wo of CaYbon aly — Carbon odour { + : Gusidered ay y, Gwidered ay gubiclituciet oot chal R— NH— R' 4 AlkyLAlKaxowine = —b N- Ally lalkanciy CoMPound Tupac NAME COMMON Nae, Clg CHa NH Clty Ne Hiliylethanawive EHyl met Ag s—Cla — NH Cl Clty Ne Stylelanonine Dicty Lauive, Ca — NH on N- Maylinefeavasine or ety louie. Scanned with CamScannerTUPAC NOMENCLATURE BB 4oR 3° AMINE: CoMPounD TUPAC NAME Ot, - CHa = i CH NN ~ dimethyl ethavamine. CH; UNO N- SHhy | N— methyl ethanewine. I NOMENCLATURE TN CASE OF FUNCTTONAL GRouP OTHER THAN AmIUE Ts ALSO PRESENT — (A Sewor -fmelioual Gvoup). Senor furcfioual ghoup wakes 2° suffix aud the quaior functional grup are treated cy substituent. dor Hho hawing of Tonior furchoval gioup , we ube PrN of thal gloup . COMPOUND Tvurac Name. OH 2- Aminohotan-1-ol Ni, C-on7 Ni) 3-Ammobutanal .. oO \oe-n CcHo > ~ Nie) Nia Nip © Payton 4 Auinopeutan-1~ ole avid. cook 7 NHp) (Nin ip Junior 03 Compare to other functional soup ) Scanned with CamScannera | TupAC NAME | COMPOUND | NH | 7 Auiline | Netz 2-Aminotoluene o” Nu 4- Bromoani line by Qe at NZ N OQ | -OR- md NIN dinetiylbenzeraniye, Be N Coy-iXO> a) diphenyl aasine OF NN diphaylanve (O>-" Beclroregalivily of No, Ariuar fon weaker H-bond an alcobele and corfoory lic acide - CeHgWH, = — ABu — 350-8 KF atuoat Compavebl hays CeHy OH — F4u — 390-3 bef op HRP, ( Due + Mroong hy drogen botsding We Alechols.) ob Compave to Awineg Scanned with CamScanner® Solvercrty + dewey aliphabe aurines gye Soluble tn water + (H-bonding ) . Slubilily of Amines OC _1 Molay Mass Reagon ~a dhe fo ncreae in Abe lydeophobic pet ody yelard fe fernections of H- bouds- (ove fo te YeOsCH = Ayournhe auines ave Insoluble jn water ), a Dur borg lydromyfon part , te fonduy dean = A6eur an avouhe Ceupcurd prep Scanned with CamScannerT fyehere. 04 = pose 4+ Chemical PROPERTIES 0 BASTC CHARACTER OF AMINES + + Awine® have an vwthared parr of elechrou over iam ae a aud hence they behave ag fewrs Rose thy geact wi to fom soluble dalkg. te a og R-Ni, +HXK = Be nua . (salt). rik oo Na itamemeicle ———_— (Aralive (Anlinwumn chionde) - Prune gal& ott dreafuent wit a bate (mak) vegeuerate the parent AWineg » a ce RNth X + OH ——b RNH, + HO + X7 Anne Sallis aye Soluble in matey bot insobable in Grgawue Solveuls Uke Gite fey — bog Kb : G faye te valor of Ky or swaller fle value of Phy Srouger is fhe base. (Boye dissoceohou Cut) Kh - — Proluidime > medolidine > aniline > O- Solitdine (v0 x10) (sxio"®) Cyan’) Ger io®) Pky (lts2 NH > Gh, > (GaN (3-23) (2.38) 2) Comparision of basic shragle of Aliphahc Auines atl Arwoula = Aliplahic auduez are Shrovgey, boxes dha auwowa oe fo +2 ( chefrow couatug pass) of alkyl gioups , due + which alectvon dusty on witrogee, ate twereond and howe Hay com easily clouole cry elect yon dha cuaronia- L Scanned with CamScannerConparigion Baste sheeugf. of Aromatic ammes and Aumonic Aromatic Amines ave weaker pasa than ominonia due fo chchoy wiledrmwoiygy padre of aryl group - | STocTuRE- Basrery Revarrowstep OF AMINES —- Bosic character of aunive depends pou tle ea of forvation of atey by awephiy a prone fan Acid. High velalive stability of colion wert auune, Jughec bale 1& Audie, © AtKANAMTNE versus AMMonzA. the reaction 4 AlKonawive oud oumowa with a Pprofon ie ured 4 Congas Hay boateily- f “ RNS ot eRe h h CAiRavcunine) i “4 ~~ i ate ee I h H Due to glectou veboring ature of alkyl Syl Ploup , if pudler clectrerr towor wihreger auc waky fe vishared oy a hove A for shoving wh Abe profer e the acid CAE efpct) Gubtbibled amuwoniomr Jon formed fom tix can gtt lable ed chu ty depasal of fotitive charge by HE abet of Alkgl $Aoup + faa baste adhe a Alea, Wecreoy, Wie (nereaye (uw adkyl gloup - Scanned with CamScanner|! On sj oder dasierly cf amunes in gortovs phase dollous the expect der I jr bse % Amine in agueoye Solution depends upon dhe atabilely of Amuonuin Cation formed by accepting pron from water « Teta amine > Secondary Anant > Pinay Awnt > Ammonia fRe anworivet cahion formed by cceping proton frou wal fachys om Which, amwonivn Galion Stability ceptuds uper folowing vr core. D 42 effeef @ H-Bonding with water molecules tb J D Ghorie Specs OD Glvahon sfgot» x a we Incree te Sie 4 alkyl group, +I effect Increays ond he Posi dive chavge Ef duronivor Cation gels digpersed wore casi ly order of Beaity > 3° 7 a7 1° Kothe greater the Si2t of for, laser will be dau delvation aud Cater stebilesed ig dhe ios The order 4 Beability @ ton, Is os pious ee oe Ceasleut of Ht- beirdersg of toon, sia: ty of Ten) K De fo aternic sepuleion of H boudiug , wher Cuumonivw ion 1 derived from 32 aunine , Slabibly fuvdher decreares fon Order — 4° Pawn > 2 Frume > 2” Ane CASE A + Ff we Combine these 3 factors 7 W tle allyl group 1s small > feos ig no Beric hindvance do hinderance to H- hondi ug and hence H~ bonding Prclowunates over +2 effect. 4 Pamne P AP amine 7 3° awune- Scanned with CamScanner; noup, there 1g Gee T+ 3{ the alkyl giup bag tan ee ovey Hence hindyoute 4p H+ bouding and heuce +2 eftect f% H- bonding. fee fore Vowin > 2° Awine > 1° Aww: Order of Metyl Aubstihided amine— (CHy)e NH > CHyNle > CCH), Ni > Ay. Order of Syl Aubrtlukd anune — (GHts},nH 7 (Gig) > Cote) NHo. > ti, K ARYLAMINES Versus Ammonta PK, Value of awiline ig quite gh because Nie attaclad b tha benzene Yg « DO dv + Teor Im auilinn ovet benzene y gop Is ohecty elon pair of ekchons get le bce lise "J ud tue Ht ig boys Gwaileble gor Protuahor Aromatic Autres ave wuikey bagep Man aiwnonia Greater He umber veeouatng Atuchere Gualer will fe He shbilify of apuie- Wort Chie, rHnk CL es Qo er (ea Cf aad (5 Rana, glorechve & for Pail - oy 2 Peseuchug Aruchere Th cow of Substitded gniline > "lect veleoaing groups likt — Chg — OCH, — Ni, [even hae Srey] lactrou wildrouy gop NO» —X , —CooH ( deeveass bear, shragla) | Scanned with CamScannerPlkyltion + Anes — unclergees altyletion on reacfion tl allyl ides Cy NH, + CHach, Br —+» Cog ch,), NH HBr Uly{ aunint (ClgQn)p NH + Ciy C2 By ——> (ejan),N + Her pi sale CHiekytanaive) (CH Ci.);N + HBy = ———> (Cece), © Br Tobey auumeniioe Grom Stwilorty - NCH), NCcitg).E Nae NHCH3, es a oO + dyr A> iy he Prciliva NetMelglouie Nprcmeltylnilive Brattain aud Secondary Amines veact wrth bc substitation veuchou + agen atom of - NH, DeH Aeyletion + Aliphatic and avon. pranary a aod ) aul and bers by wucleophi fe yeachon If couricered a vpeplacomnenct of, yc Soop by asl giorP > fe techen 16 carried cot im Ke prtsmce of a Shrayer bax thaw cowie «hich = Yemov HCL m femal. | RH, + Ricock > ANH COR' + HL | (eid lori) '| R! “ iP) ‘ | R-Bea + ect > RW el a» RN-c-R' + Het | h 0 h ad [g-tmin) ——fhcid (w= bth baled (bu.) ma Scanned with CamScanner5 hnatd Sn + Ch, Co-6— COCK, NH COCHS CRaalic Aibolnde ) (n- phaaylefbeuatide) oO Ben zoylediou —> Trcbrodu cing Gls -E— grep 4 wolbraule by treahig if with Benzoyl chlovide Im the presence x bon Known 03 ben zoylahion- o i €y-80 + (gts Coce HOH, & Sone t Gets + Hel CSchoHen Reumann Yeactiou ), @ Carbglamine Reaction = — Prusery awe on hrating wile Chhvofionn and ale» polassiow hydroxide few iocyauicey.. Algo Kiown aS — TsocyanrO€ esr (Test fr 5 Autnes), R-NH, + CHC + 3KoH —4-» R-NC + ZKCL +340 Cly- NK + CHels + SKOH —2— > Cy—ne +3kcl+3K0 (ols NH, + CHC, + SRO A» GHeNc +2Kcl + BLO " Scanned with CamScanner