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Amines
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AMINES ies 9.1-|INTRODUCTION Amines are the organic derivatives of ammonia in which one, two of all the three hydrogen atoms have been replaced by alkyl, aryl or aralkyl groups. For example, 4 u " cHy \ 1 \ I H-N-H | CHy—-N-H | CH)—N—CH, — CH;—N—CHy Ammonia Methytamine —__Dymethylamine Trethytamine Amines from an important class of organic compounds since they not only serve as starting materials for the synthesis of other classes of organic compounds but many of them also possess profound physiological ‘activity In this unit, we shall bnefly discuss the chemistry of aliphatic and aromatic amines. rs CLASSIFICATION OF AMINES Amines are Classified as primary (1°) secondary (2°) and tertiary (3°)* according as one, two or all the three hydrogen atoms of ammonia are replaced by alkyl or aryl of aralkyl groups as described below ( Primary (1°) amines, Primary amines are derivatives of ammenia in which one bydroyen atom of ammotas has been replaced by alkyl, aryl or aralkyl group. Therefore, their functional group (s the amino group (—NH,) Depending upon whether the group directly attached to the nitrogen atom isan alkyl, aryl or aralky! group the) are called aliphatic amines (or alkylamines) aromatic aminey (or arylamines) and tralkylamincs respectively, For example, cH, NH, Orn Oyen, Asians Methylene Heazylaming (Aliphane amine) (Unylamine) (Uraikytamine) (1) Secondary (2") amines. These are denvatives of ammonia in which two hydrogen atoms of ammonia have been replaced by alky! aryl ot atalhy! groups: Therefore, their functional group 18 the imina group m may, bevuedary wd teitary weed here have different meanings than those used in ase af aloo 2 aad 3° akobols reler to the type of easbon to which OH is attached Tus, 2-propanaiine w a pritary asus but 2-propasol w secondary alcohol be noted here that the Wei i» Iu alesis, 1° cH,—CH—CH, CH,—CH—CH, i | NH, OH 1° Amune 2 Abeohol @ ‘ larcreereral il Scanned with CamScannerty, eign vine eto te he ee enacts ne ed Pare mesma AE age tm Secteur ne wn eo ata aban GLO Ors tect mombert soc hongenie an mteraelag cena ree Reema ban Seecortase efor atest Oto a ee ‘quatrnry amen compen aa ow on he pe ms he ae seceeeetcteie seater desmnatankncbexp yrs cmc nit (where Xr hlogn hone ome) raven om cat 8r The ne fai cl ht of ncn. Li in ami None a Inked haw of pvt ntti oe enorme eer tad ae asian wee bonhcaismsinsiocpaathenoa: Reccpie ers ‘Setetymiae fem lo 2 a s ho 6 bond. eS ni pp ee een Pp orem] {doar Tor e rend anc Honor se Pani tr se hae fee ee mana tnmatiocsen 2 emanate en Se Ore ccmenerer ven -REOCHEMISTRY OF AMINES ear arc ee ante pe RN ne pred ped oa ‘so then meen Seemsrometmhnpestonas ity al 3 ese iy earn onset spt ten roan Daring tists, es thyhan of Nhangeton pa wend ‘ate thn theo wt tg sie ere 7 eer panne wee ols a oe) mas ‘iss te of incon er Wah 7 = Pe) ee, ery mie f ee 11 hp chin etre anew cot Dc rod "Sircssinypyinenem ie arbors to op ne ae grsmen ett, ie fone: Tn on Nts Scanned with CamScannerSoccer oo smears ene ag ec ml he oma sts aon). Senae eee oe tts at rameseemcrne See ere cise tasters ro ae eos nt ery aie ame gsi Naan td NIE sm neces ete cst ore, Tuaneof aye, eps Inn pant anni Tari ei “cmd UPAC on ne sas nite re ow eras, ‘rine Anos ‘mie Gxgu ene, | Pomme mespomne | Leap Propane TT setae Asie Seay ate: mM, Dinan Ntenctnaiae Oya mc, tne ar etpananie Netimasoare $2 _____aamsoiccmnevenm ‘etary mts: cute, na ‘i emo Htc, | r,roetyesmcpnine | gt etnamin Oroigm, | pegtiniseeMeaaomedaar | Penlnedanaine Oesigay, ‘remtatiytamine se 22Pbenltianamie, ‘cierto nc tt err ies ah a fhe al pe a eo we ‘ate sn seen i poe mean Se ion one ot eo ‘Remon tte sent soae thoi Force we Suen, arti — bbb, c,h 2k b,c, nce pn cis Sie it a end rgrddimon ri Sibyen toon xpi litt ea org nin be ot noe i so a hon cape Re soba bn, incu enien tfage ares Kn cuore, Scanned with CamScanner Aene sensi niger Soares eens scenario =e ree 0m be re api at the compe name fai ia ede ence amie nf her ies sey writen ron wed ooo =f. Oo =e oO. ~g~ Sess eet by anaes, esi, i nw lS in connor res no frosty uh he sna ame APNG heh seine 2 —__ eeecumvsem i PREPARATION or amines eH pret fe ntl : (Reucion sie compenea The i congrats ei CERIN Sis acento s e “1 ‘ire conpanl cane way pepe ys ce fetes he tad es a ‘soins peptone psec ns !e sow bere nme ip panos Onn Ticsnee Oni m0 om date npn at ee rece gs ch nei de ‘nf omn esta Sp Fron ; cy G oye ABBE, cue C)-vee ome zaman an wan SE ge can hom me ‘ova eon ta ed um ance Orn #2 [On] = Lior im ye GAB tet etna ot tt 2 + SOF 401-10, 43 PEER, crema 3,0 ‘neon ase aco ler tnt compete ace maton ec gp i abo ay ‘eine mem ype ears eben "Tg Scanned with CamScannereS RT a 1 rma mien easy PCy he ayn cher rt nd lesa eae es 2. By the redeton ore dpi andar sedan fe coating i ae esl Tin mind cm ad bl Ganon ay oon a ot “a as ingen ee oom pase os On ie Oo O-s0 Gamma Open = pave rant Si rec poy ect fh so RS ne ye Sse tard etne OSS sarees at phan nox FES on EM poh rn saa Bry sim sie mt as nt py ae KE be a i ee citer AES, Gace exe. 2 Relate smile Pima andy a trian be pre fom lh snditunrtyreuctetaaon fee Settee cfertahgare fice anna ‘hams m proc sigge!The ecn oy nape seme aaton 8 xc EE, xen mcy, pee a cans AEE. epson paren co nie cre cin pte ine. The tn inn cid ‘Seay wh Rey Ni 37 Kand 0a precast esos (ABH, Sod sac ary, es ie be aie onto bl Non ees s img oes ely tent ld ren with ames pro bog ile cae i Tosa] mem Aa eagle seme Sot, oo ce ayatiecn “28% cxoncncren, tome soe cigoyeiat, SES on, —er—ononan, Machin, Rete enna anes hgh ered fron ft ine ad teeth lose Se Selb ey 3c te | So gat. sagt Deca Dean _ Sans rc cet tai cee iin alee Scanned with CamScannerwcheowige cn as fbi 2 er aice Oo SH [ Oearves, ] A Gye se, Sit ry ai me a de re eh ay amin Te Hs og (cua crore RN bt ers ks pty mtd rte porto prmay anes ating secant alos tegen). cl hs tines eis prep fan amano of ty hate bcos oe endeey ser a tae users emnaen nitions Th primary nines ome ding ete anitioncn fuer ihe ay rks frmacetn aout fhe sda) sine Thisan over bevel by Ug Ose “Gabriel ptalinide rae. Tiss wr comeniet mtd tbe peptone phate end lot ary amine. Pihalie cea ou inias poop (304) Ted to eon “Tihowig sabe ig and hence bye he ini psi Theor pili “beens Semered ino porn thy teaent it onal tata fests, Ferm palin o ang han i ort be, ges ecvespnding Woe Poin TS up draw ht HCl ON) under rs Wi ling a es ima amie Cees ae OC Dee +O Oe Piha ad cam aun comer int pide and sd ove an oe ain Simi enamine cin be prepared by sing tel cies eine (NCH,COOH) ty sing herons ta pce fey ide nthe above en, nya (lrnoge en) o Nalbandian connie an ent nee a rch frei ances ong Gabel tes or a eee Se Oe a mc si bee et iar anies sa ome acer) Wh scan tee spay ee CON BOW RN ne F040 #2 cs ee Sah keno cox, - Gees ‘Mecanismo HO) whines een Te ye0—ronr Br rio econ siete athe louie wipers E Lue 3 foe eae nein On ae Le, web Es sent es rere steps t-N=C=0 + 2408 pay 00, idence pet of he mechan. Ti energy ein at eset at exgasoe ae saybent rs e ScSon Thee nme epee oe wn ee DH Scanned with CamScanneree shan ue m meta ee ei cnc fr nme mnt oor Seo ° ~o ms 1 ean, 2 a, Ean, aaa? OHMIC OCH Far ON ERROR Mean oie a ey ata ‘en “The tht Wma carat sty forme an of CH mt aera, anteater ess ‘CHy,_N=C=0 + CH,0H—+ CH,—MIL-COOCH, Maayan Mes Neatertte stereochemistry. bg inte above tin seen how hat te 3g the os Be tterm aminitene Gi) and te 4 etng eager of eo Rsom carbon fluor. ‘Siti Nat scur este, poche yet ate sugges he formalin of oye ‘ermatins i ee tens Tec spaced at ot se ps oc situa = ‘iced belo tn ster words, Hotaan orem ia none rearangenet in which the igang oop be from etn oven sub oon cows. Tha pre ye eros ‘Sareea soe amid pe epcay ce amie (0) wih renin efits. emo fg, mae, — a, Be, SS ne vs (6-2 Bemlpupt 9 (Shp) (gistPanszion oF wammany, seconnany AD TRTIARY AMINES Cerain maids of propane ck a ammonia all hale hese primary (1 sco (2) a etary ane") qustemary aman sade AE chained component St sl ia KOM when quterary amon ‘ing nonfat ns hind wee tu ae te er, The mea snes = (hata ten separ ye lloning mts 1, Pract dain Arist oan" smn canbe pratt in iniul compan ty raion siaon ace ring poss rey spa Foremal, cuciN, ceuarigat (cre Ami 06) Pie 96) ane) “hiss he mont ntaor metod ans ow ws indusay bev ofthe vay of EY titan faonating estas han pute site abdos even he otiag ae te meres 2 tinted corning i of Te KOH lao we te it mn itn ie cas et amines react dierenly as dacsed below s. mi Ccray meena = naa meni fe mnt obs ola elt Algernon nbn ede (i) cry oie om ly enna ich ee of be ype enon at eh ROH Ofte xt wo OFX i, ran a ne et ate i tiga tod ee tin A ehh oso an bee pe De oe er sn rire by rei wh Dy sin Tet ng ann banca om wich eae ae Ee oh Oi = O-pe + me “tne / Tonigner + OH —> RN + Cl # HD Ole stOfe Dee Raich # NOM —e RAIL RCL HO cetyl oi pel ponent ni cies = ee Scanned with CamScannerer 4 Sy-to. + wrenen, 4 S)-somesen + ‘eigen Hott tt hr Wray ato at satin toe rip set ng en ecto, ‘cue cae, sje, Shorey cn meee eta ‘SEESSSISRICAS Att sw fr id et mtr to) D9) and TO eco mu cg a Sia, % BA rer Sais oe a = eon Not : 2 cave ee earn enn A rt cay lors co mii i se yeni ng Gentoo oe Spat Scanned with CamScannerSUES ac netsemectoumeamem meme “_ peng Sosastsneacempsonoe once | | crm, | areelem | caren Scanned with CamScannerryycihoah ane I on, aye =e occ nen ofa coe mea ome tie i pio ent tse ont ns ee lig a sar ean an a Serer ee re ance a Spirehieamaantiaren ante domenica Sram am th ASS UE el ia rr hn Sem et ei ie mela caeg ratte Shermer nara quite pee rainibcatcmetmea ‘aime acne te hn waders raasianafay Sarasa Ca mente pr prin cor mene ehent lows ese Jat hg) gry sha atin, sce “wlehdamring inductive effect (or —1-fect) ts ta iSeries cea ela See ps Soe eigen ptm ELCHLEROHNN, > GILGEN,» CCH, | acl {We Sree eget VV emp mc ‘Seenrce oer cts an ado hep non on tc watjgesinion Onacobr and. ncntonnns nia eine. 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