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    Iniya Rajasekhar
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    5 views30 pages

    Amines

    Uploaded by

    Iniya Rajasekhar

    Copyright:

    © All Rights Reserved
    Download as PDF or read online from Scribd
    Flag for inappropriate content
    of 30
    Amines ave derivatives of ammonia in which °he Cor toms one replaced by alkyl CR) or aryl.CAy) groups —___ 1 Blocd pressure cold 0 dentistry ae 2 OMmP LES: Adrenaling , Ephedrine , Novacain (araustetic) _ Bendy 2 Cant Wis ba mine drug) es Ns a a ee ee Nts * na? 9d Geant! co [| rae c | fav Grund Hy brcliced State = —state——— Hy bvidisatiow + 453 shane i ouy yridak 3 ae e4 a 1 anole ewe : lof? ey 104 Baked on no, of Hydsogen atom $ replaced by Ror AS gioyps. “heel + Bosed on Similour ity H ios sn aie one buys 09215 9, mont a €% youPr mpage ae They ane am} oayl9> A peNige t An eN eg 2 ee ty dogs —____} xépiawd by alley \_9014 ps °F ody. |_ gone S— t 2H seplaced << 2 = NN (ox) (Ar), = NH | nn as So +. Based on Similonity i _ ae > Simple amine arts Cit eee amines whew the same alkyiZoryl 9eve 4p ant present — iS Called simple amine x At id A a ty = NH tg, Hs -NH= CoNe tt, = AIH 5 > mixed: canines 9 = Amines where different alkyl / aryl gcoups ane present Hans ica ited= waite dm rine Sr ane es | es Uty-Ni-C2 Hg, Ota N = CH 3_ ‘Nomenclature of Amings -—_____ Step -Cii) : lowest num. loon - - edd wn mined shail be gene r Step Cid. Presence of more euaatist eink S—— J Simi ton sites Sues |e een Foo alphabetical! 5 Step Civ) Presence of enn e paral dag son PS SSS Pies rie nea ike A tri, +o fhe a se intnav et —» ethanaming alia —_—__— — Ut, = oe Sats poop on ~ A= Omid i a Se a pre pana mi ne, ___ NH, = CH, - Cy, = NH, => Ethane-1, a ~diiamine 25nimA Jo mde tte I ee aaa Ra mattayt pro p: On oe Bie a a. me \=_P10 Panoumt EE SIME AMINE Sain Dae Sue DO nMines ee en) Solgest. Hhotn Sule ___ Steptid:longest chain rule __ Step Gi): Ortior Groups ane _ Step ii): Other gr0U pS are oe Substituents Substituents este pili Pre ee (in) ona. i ee trl torre ave: vsedi | be Betsy WAL Hao india induae ASL ath ic gh = min Duna hie Cin : e i Nu aa ats eho) alien pe ical ee ay and nd a wit JAY yi Clodsification LLPAC Namo: —— = a ea Ea. Classifications A ba srt oe he PAG Nome: ous ini oh alas bes | i ” ii i i cid uh BR omc LL _ Classification: _turac Namen: pt eh ot SL IDEAC Names sis webter LSE OSH 6 | Classification, a i Pier eee RSLS es ni 5 Classification: iV PAC Name+ ses sess Ler ae Preparation of Amines i = Reduction > Ammonolysis mabriel phthalimide synthesis Nitvites C- on) eo — Amides (abe Ned) 4 ‘ . 1a) giepladasecndt = —xfrone Nitro. compotinds Contaliytit: hydiogenstion,) Pd -NOo + eS ae ours on Why con't aromatic amines be- be formed using GPs? _ 7 Thhis_is be camse ory! halides do not _undego nu Sule dation along. with anions formed. lay pttraltvnn i che, 1 | Amant leas tron t carbon atom present iva annie Ay "lo prepared by Holtman lrom amide Bravado TRAC, — Phy: sical Properties - Dies 3 1. Physical State ae aren : ae j—bower amines = tases — Ee Higher amines - liquids | Solids — — : a a ! _ + Colbur af fi <7 ——1__Usvally colourless byt relour formation tak e 42 _atuospheric oxidation (during skorage) -tgner eninesattones ee eg inleohols > Amines > simple Hoes pane _— Reorom why alcohols have more jovi ling poimk tian am\neS > Zs ee + — During hydrogen bonding , alcohols bond +h74g bh exygen. while. dumines bond through nitrogen . Oxygen has aw ——_— tleebonegativity of 2-6 which hold te fond closer Hen the mitogen which nas on electro negativity of 3:0. Therefore aleohols have a higher lepiling point than _aminess ote a ee — Amine __ Compound Molar mass Boiling point __ ES Nes n= Cy Hg NHL ob 43 SLk oe Cestts), NHK $3 Bde ee tla? Cos N(CH), Ag 210.S K ag —___|compovnd __ Fox la. Molar mass Boiling point __ WE Alcolol sn tC Mg Obs iin ge br apse aiaee eMC sa bmine Cotte N( crs) sds As ees a VOT GniS eee —____. Hydicotastbon. Coble CH (cts, O54 as eee ee EH So lutinibity | it pie aie a cal Babi ve $B | Solubility 96 Hydrogen) bonding ie ai Re SN Ete | Soto picey ot | H ine: mobic phiue Hydwearbon chain | Souuei ity of \ Pol ot ai MoloA mass See ee tle | en bale i becky, OC Hyd dophilie. poak. ee ae | SS 1 a 3 o Hydrophobic Patt. Base Acid Ayre eee a ReNHgXx> + NaOH => R-NH, + Nar + 420 RoNHg x + Hy O —— > R-NH, + HX + H20 sHydrolysis regenerates parent amine -fyo: “Pumimd salts _one able to dissolve in HO yo a __@ Which is more basic? dita Bk ih a date | eee S Aiiphatic amine Aliphatic amine oy aryl amine oy ammonia Alkananine {| Alkyl amine ——} iaheacesidieeesliasns ait ee wl eae fee of amine — el Pie Site 4:38 Awaonia i |_ae> je > 3°>Nity ‘acne a >3°> 19> NH Lethyl group] ee othe eee _Reosow:! uN = ei Rew (Ol Ne > Oo) Do ee : ee i ___- Soh’ on ern pe Ge die a ce eat arg! leg ond weaker bases than oummol +} Dua_+o. ection ut | Hoare ivag Choracker 08 Oni “Group, ot mitre gen atoms to lee in UOnj4gation atte ten soa 6 Ting, S makes eee saa) pouus. (WAS electrons, ——AwmUnium ier forms only 2d resonance structures. Atm ne ssononce => Less stability => Less basicity ortho i Paro. > ertice > simple. ahilint S meba. < | ituents one pres x Lg tae Substit * 4 a | ne ie) least baste. x Zt sai i : Si 4 = ae eae | a Henent Isat Lf the e iedmng—* | bonteinois ng Ce oak > meta > pana do _ Seed. S abstitvents ane _attached to =.Nit a RHO? , Garicity ord er: | eS ee i : aps q in the increasing order of basick 3 _pmiline , p-ndtroaniline and p-toluidine NH gus ete NK, te He ce pital sins eae Og Nit tne sided Gaby ne ¢ Ce DA tat _ 8. Arrange the following in derwasing order of posic Strength in Hair aqueous solution Co PH, Cla nt, Coby), NHC CHia a fl Cots), NH > CHaNo Uda 9_N “Nita Chemical Reactions — = ___ Nucleophitic substitution Reaction ——— ft electrophilic _ Substitution Rea ck iat i __inucleoP Hel c SUBSTITUTION REACTION — __ > Reaction uot acl Sas __ 2 Alkylation __ tack | aaiostio Shee #1 Reaction withory Lsviphonyl chloride ne LREGCE nig _Brominakion it nitration ee rr: 2 Pe ee ages iin ie C7 as Ecenpial ge (Chto d— NM HC N= mo tiy|melfiancmi 02 __methy| ammoniim Sulp ha : 5 ss Letts Do = NH Has Oy C Cuts), NH2J2S0 | os 4 Dimethry |eummeniuen ir a Lets aN 32 HL SO, == Shee os Rice "Ia-s0 2 Ter ine. 2 UNOg ——> Cen BO mstENts Tri Me Hay 0 —HeBsGsia Aid Cou. sidalbl et ei Cend L-R-NHp +HX ——? R-=NH3% ne - - gy Ng ae methy laram onium chloride CH, -NK + HCl pe a puiasociih Ai puinialict sacha Bp (Cg d5 NM He) ob oN CL N= merylmetianaming _Dimeaylammmonismehleride, Timothy ami monris (tad. + Hel Ccts23 NAC Ritts Nita) + 4,60, —> Conant, J, soc) Methyl ammnoniting Sulp ha 2CU4Hts ),-NH +H + y [ es 280, ——> f teu,), Nit, 19.50 ~ Pienaar cummaoniven 2 (eri323-N + 1,80 4 (ehs)s m9 soy” ~ mith YL aimmaininen sul oe a Cx oS ects tH, COOH ——? CHa Nit, Coo CH, Ses a a ______Methy|ammenium acetote _.. (ttg2g-N + Citgtoolt —> (tts)2 NH tcootHs pat tn. Trime tay loom monivmacetate Nite NH cl Wee nb ead frm amides by nucleophilic Substitution resents of base (stronger than amines ¥ } epic aa Base: Pyridine (Te Aacittate forward genction u dissa® byprccluels> bas € CAs -NHS + Bo ste OCS frye eet ECO Bl) “Mecthanommine i Reotylchlovide co ve base “oe ie Ots-—NiH, + CH, COOCH ——7_cHaNn HCO Crt Ook, ie Me Paomamind Aethiconhydwde Bos: : bare ee Hs - Nits + (rt, Loot, > CtanHoocH 4 H30H et Sa A Noe 2 amine (Nn UAs — N= H 1 Hts CH co ce. “te Pt $$ ______N- Flute a le tie! Ch . bias Cacetonilive) — ae isdn nied iphenyletinanaumide S}.__— 26 BENZOY) ATION — cee CHa -NHo + Co 0 Cl eres = Ne ep =e Beary |hioride Prue Nis mettadlbenra mide > + Reaction ith Aryl Sulphonyl chlorid eS ee = ° | Ns elon elena, = Se 1-32 amine does pot | Eg HC iin SS ° | 2 | amin’d Caissorves SiN ALIsALL) ° R-N=-H + cu =+§ ee tag AD iit Aa ale a ! N- Man! f (otite precipitate) U Le i CINSOoLUBLE PERNEAN IS) — 42? aming C1 ° ae =Her | cae c See al Hg —— tH wigs CS ee . He rhc | ————— og / +} Preparing N,N-dimetaylbenrene sulphonamide oe or ee eee eT mre ies & us aa NS Ht cl = s eat Me? Wy - N= =S- tots. Clty ° : tts i os Why dors the product of 2° amine and hindsberg reagent inot dissolve jn an alkali medium ? a 1° amine 's product has o hydrogen whith is more _ polar (positive) whith makes it an acidic substance. On rr ction wits on alkali medium, it dissolves to _ form woatey anda white precipitate (salt) re jena tort hot Po ee ___| Therefore, ik does wok dissolve in alkali Eee 4 = _Carbylamine reaction (1°? amines) See Aka Corbylaming test lor) Isocyanide test (or) Isenitrile 4 | R=NH2+ CHttls.4 3K0H >> R-NC + Biscl-+ 3H, 0 fein withanibvous! auidiie gene ee L >. sai sali EE | LHNOg iS a Mighty unstable acid and. cannok be | e +estS. 7. a | le Should be prepared freshly while deing +h | ce \ L NaNO, + HCL— > HNO, +Nadl———— : | = || Sodturn nitrite, Coo —_— | 3 EM SES a_i _oumine — : EM Noell tiene rer we? aie | aa ee % i R=NHy + Nano, + QH¢lL—> R-N, + 2,0 + Natt — - < Ee: ab aru ie ply ldiazoniued: ater — Ye a 5 tt l ae Pe f | evi es is o0en undalele’ On ven ities tes teem with the water in te test tube. it ies -OH + Not tHe R- Ny, + Ho ——7 =O tees __>_ Paeparing methan Ol i eS ee ey : Udg~ Nig + NANO, 2H —? (tao Np Cl +240 +NaUl | | Ic, Woo + Heo > eg kt | i eeierer ie 3 Ds I oe ety atl Btls a fg NTE asa 4 ‘ _ * eee hen 20-5 GMs Dit Nyt + BO i This press 3S called dioriotisotion (step | of son Ee i i) Production of Nz gas will b2 -slomey in ovomatio. Se : Ria tcN20 a HO | HolNo. = Nikrese omind Pcie er layer using Leb : 4 Further ta divarippaucaneee= oot. oe Soa +hitbese test Ccnapker tl) — —— Hlievermann's be¢k oe Liebermann's tect + Hy S0y > pro, 18° amine + HNo, + G,HsOH + onc. 250, faa product + Hy O — > red produc - shed. product + NaOH /alkali > product The absence of Ny gas on further heat 49 confirms pe the vse of 3° amine — i Be Aliphatic ari me + HNO. iM Aromatic amine + 14 107+ P= naphtno lene => ©Younge= Pe i | i ie oe Cy ae ae i Ay i¢ amines it eNHe 3 j IL aTieISus 1° AMINE BO AMINE || f= car bylamine Isonuitrile | No action |Ne action | | test RN] Cise cyanide) : . : ee testa CoN Lise ty snide) | ' Amine + CHCly Foul smell Ain. i eee con oe ae + —_—_ + — a af 5 || Hindsberg reagent. |Slphonemides |Sviphenamides ees Prine + white ppe vwohite ppr i gee Hinsber9 reagent [Soluble in alkali |insolble in alkali Fr Tr “= A | [Nitrous atid | reddish brown) elo eily | Salt seleble Amine + NaNO. | erfervesenge { pubstanc | in H20 + HCI of No [Wibosooming)| Kan NOs T y | _ | Liebermann's | L cahis. Nityoso test Amine + NaNo, +H¢l| + phenol +cone. H,S0, | + H20 oaReurte | 1 | + NAOH ____. Test for Aliphatic » Aromatic amines. | TEST [ALIPHATIC AMINES | AROMATIC AMINES HNo, test | Aleohol + Na ? Diarotised product |||) T _ +. Aming t+ (Reddish brown CwlWite pet) +p gas) / << | pcodye test ¥ Orange red | amine+ Benaphthol - ane a 4NaNo. +HCl . formation tf oh | 4 | Eleckyophilic. Sulpstidaation Reaction aed re Tawa X, : & natn cae =Nn, group is highly rin \ acti sae. g tin ve Thesay ‘ ‘i ivoatives. | Hie products ave tri gubsttuted deri —— Reet la eee il WrereLeltoknas yo be presets, aa 7 ao ‘bg teo-b lary © Peers Cot i ‘o > wv Se past ea 7 _ Aetonilide Ree ae. ene eres tee ge ig aie eee SS Note: — N=COCHs grup is less ring acti vacting, than -NHy Pei OE Sn aa aa Ci sro. heh ORR ee risk oa Nino, Jo or ~ P-bromo amtanilid _Nitration (ny a | = | (hae mixture - 4) S04 , NOs te a {| a Serer ines ft a Lo. Pie aor Moke: m- Soe pacity dm oleae ee move oudi iting CN iGind oo hich is meta directing, 9 We DE pad ae Aa” io : Nt | 2 5 Be pe ee (442%) (sites? | NH2 . UNC CH, Brees io fa 8 -Bree a i | | — eee = See: EEA t NOCH s HUICOCH 3 I fA » Nihoting mixture $ ji ai = > fy | ie NA RANA & Te _ ma ae t ‘ Su Pe pets Leaie ce | SS jalkyiation andoclation? 0 Question: Why cant amines perform friedaloratt's | fH eredalemtts alkylation and. arylation is wot 7 ee § I i -Pessible because. | -— Amines ont lewis bases Celectyon donors). = Catalyst Alcis used in Friedal cats alkylation : atylaton ave. Weis _ocids (electron accep toys) Amines and AlCls react 45 fonm sales 1K. ert ta. ae ics a OO} ———— Pili he Et Nomentlature of Jinzoniumehleos einen sehen 8 ee eee ee Bont + Diaronivm + Anio tases Ht ee CU eNS Cl Reine dinner te NS Bet 2 spennene dia zoninin bromide i Gs No HS0, = Benzene diaronium hylnogen clprale. Oe BE, = Benrene diaronium ftucre borate + _ 7 Preporntion of diarenium salts(piazetisation® 2793-298 K i Pe Sumo, S t tay | dicen’ vine claberid @ Ar = Nite ct Nano, Hel ———> av Nye +2H,0 Natt - Phy sical Properties + Colourless cry st: lline alts Pee | Sotble in HO), reacks | ohile. arming . Me i chemical properties sito iid (i f= Displacement of Dieta sreug (he 1+ Retention of Dia20 groupt=Na)) + ee ey aks : A. Chemical reachons int welving displacement of diare group as EE oe VEACH OM dm aes 's Reachon — \ 4—__|__ Gtalysts: Cur tl, , Cu 1a | Cor $el, / HCI . i Fe | ener ad Oy gC en6r2 /tHer | Caen / KEN Aaa | yet i a A SG Rae ene 1 : sabia Replacement by ledides 1 = Ketan iG tia e SS iyo prise Node lscil os ye ae — ——__Pryliodide___ Ay Cl +Na aAxvBr+Na —__Flucero boric acid seals i eu i ___-StepGis. ArN2 BPI pee fe Aryl fuori de -, Replacement by nity group _ Ria Wolcott wei, | FL Replacement lay Hydrernyl group me | ——— a SY £ “if csi ts a ANS clon tg eA te Nee : Betis Se, VI Vreicas Hi hi i ‘ i ———— reactonhs involving retention of diare. group. oe => Coupling reaction : ia ' aoueg Fig PO, + Hy 0 ——>ArH tNa +H3PO,+ HCl | NE ag Hy Pe ples phons acid | tke eee aa i Vou" 4 > orange. dye, ye ow dye Ses Ce ee Vi | q —— Bi a =H Coupling reaction eee _ SE tohen dicronium salts i i cémpovi ! ie ny s ia like phenol, amines, ete it undergoes coupli res } ih the formation of bright colobred 4 - i fore dated 2S toy pling reaChon

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