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Organic Reactions Addition - Addilion of atoms /grps to unsaturated bond -Removal of atoms/qrP resulting ia formation of double / triple bond -lLose e- - Gain e7 - Lose Ht -Gain Ht -~ Lose O07 ' > 2 5 oe) Condensation Hunc-gy 4 - Combination of -Reel 7 H,0 to ~e 2 molecules ~ split the compound | oy- elimination of hy CR a — Deen hax. te Small malccule Simpler substances _ Rn 0 —O—H Hydroxy! group — Replacement of an oO Glom /grp within il Carbonyl group a molecule ae ie] ll Carboxyl group Nitriles Organic Family | Suffix Example mf -ane ‘—H| Methane H Aikanes H H rene bed Ethene HoH Alkenes Dee: 1-4-4 a \chloroethane cl -ane G4 Halogenoalkanes H (—) -ol H-¢-o-H Methanol " Alcohols -al i Methanal HH” ~H Aldehydes Ketones Methanoic “oie A fae Carboxylic Acid iki oo -| a= Esters a -amine eH Methylamine H Amines H nitrile H-G-cEN Ethyl nitrile Excess Oa aly 1001 B)0, 200, +30 limited O2 CH, + FO, —+ Co + 2H,0 CH, + 0, —* C +2420 Combustion [Heat , 02] Alkanes 1 -¢-Cc- t 1 Free Ce Subsiturtin {ov light , cou, | Solvent [iret a wast] Halogenedion, Xz Ha loge noalkanes p-X WN © Initetion : Ce-Ch en" O« 4 @ Frepagation ue exh ay Oe — He e + Reh Cen] u coterie) A cc ck [2 radials cole] 7 @ Termination» CL 4 CL hy “CH, + CL CHL “en, + CH, > CHyCHs Oxidation Product O Ally! , 2H 602 #0) 4 - 4 Yer fol ene +... +0 conn <2 png) Ho” m ane e-c s[oJ—| pe=0 4... wf H 20 4... [ra 0 ia ‘ou 2 Allyl, OH Ry RL Jee’ +f" Se= 0... oo ae Electrophilic Add ton Alkanes eSte9 1 Pihelogeroalkane Alkene /Alkyne Can't undergo Sn 1, Nu cleophilic Subsiturtion Alcohol a! Ov R-G-x Ma Nudleophilie Subgtuction 1 2 — + R-c-OH + iX 1 a“ Cn a oT “ Sy + cbehingy + cuncastan + nar ft eas wie, pasta og Cant underge Sn 2, beuz I° Carbocation ry not stable | RX 2° RX beuz 3° RX have SS 4 Oe - a on-e-W + EX “ie Me ade Cont immedietly perform nucleophilic addition -o ost nly elephs sllton , lo many ® geps bl Slee hindus a F qe nae AY Beco 34 Tare pring (° Alcoho | | Hydroxynitrite on 8 ' Ken + H,50, —* K,50,, + HON r-e-n OPH] — R-c-H “i . j I Nucleophilic Addition mechanism: i) © Step 1: mucleaphilic adcition of CN- Loil-] Carboxylic | fCn01+ HsSPee}) Aldehyde R Oxidation acids Rethr q : 7 at ra = = aun" 0 Me ge on ON a PHO, pe tO) a Si ; | Sreecmerreirceg “ose eos 5 reneicte Wer miroc * Ketones have na reaction with Tollen’s reagent. cE R—CHO + 2Ag(NH)s* > R—COOH + 2Ag + H,O + 2NH, + 2NH,* an : se o aie, 7 tain! = 30mr he ang + ce + ac +220 Ij ROO Nat + CHI, ca Only 1 Ableiyle gide tue result 1° Alcoho | Hydroxyniteile Kony + H450yn —? k50, 7 HON Nucleophilic Addition mechanism: oO oH u ! r-e-k t2fH] R-ER [Shorter chain] Coreen 400, AUD Jnvsfugs bosabeng a C-€ bomd and CO, may also be formed “ AACOON + ACD, + 2H , ewvetshdl fag «(1 ob enioageoow 4 R-c-on + HO nf F on) «neo, —s9[n-E-ornet]* 60 + Hho ys eat a e Alayt chioide + SO, + HUL Aly Chloride *+PO(L, + HU ; p & i R- €~oH) + SOG) —> ecg * $+ HOR R-e-o8 + PU —> R-c-ce + POC, + HOD Ovidation reactions Reddish Brown ppt © HCQOH + 2Cu?* + 40H > CO, + Cu,0 +3H,0 (blue) (brick red) Silver micror * HICOOI | 2|Ag(NIL),]' 20LF > 21,0 CO, % ce VANLL | 2Ag(silver mirror) ¢@% % A dj a * HCOOH + [O] > CO,+H,O Halogencbenzene + HX © Step 1: Formation of Br* a Be — Br 7 Br rt + [Ate] * Step 2 lect aztack on benzene ring, ieee” + sep dba pt (a) [Meal -6 “a Bie + AB Nifrated Benzene + Step 1 Production of nitronium fon, NO.” FING, # LHyS0q = NO! 4 Diy" Mot © Step 2 :Electrophilic atizck on bengene ring an (CJ) w ' Stop 3: Lost of proton, © smear — Gh one Aly Benzene * Step 1: Formation of electrophile carbocation, 4 @ . mee La, eed atts au) ‘ « © Step 7 : Flecsrophilie attack on benzene ving. ‘th ion Tena © Step 3 Toss af proton ty ‘hal oS) + [aca] -O 4 HU + Abts y cS Ketone * Step 1: Production of nitronium ion, NO;* 9 ae 1g ce ae uo oyto 4 (ALU) i & * Step 2: Flectrophilie atk on benzene ring So Spat nen m5} or of * Step,3 : Loss of proton.” "ety Pech o + [atl -O +H ARs Cyclohexane Niteated methyl benzene +H, £01 Stop 1: Production of mittoniura len, KO, Und + 2Hj8Gq —— KOA Uo” 4 HOt © Scop 2: Eloesphili stack on berzsne ring ol Ye — 5 Loss ot pas Eoaadm Tt woe, oO Alkyd wuthyh benzene + HX 1 Step: Formation oP eleetsaphile carbaeation A . - wt Da iea asia + fey « © Step 2 : Blectrophilie atack on benzene ring, » Step 9s Low ot pet : t » Pay Cf -G% fe) is Ate a ae) Ketone + Ht * Step 1: Formation of electrophile carbocation Re. 4 . . Wee hk co [AtU,) ‘ 4 « © Step 2: Electrophilic attack on benzene ring E eer Seward fy yo, or eo In ® io —— senio Fhe Ow © Step 3: Loss of proton. agp ee) Th nm no et) WS ot catacin ler ia a fin ff + [aby — 7) Ht Att Halo methy.t benzene + Hx Benzoic Acid mane 8 Any carhoa gronpton benzene ring yall be axtdiet] lo COOH. Addition - Elimination mechanism Carborytic Aad + Hee ——;, Nis ; SY CH,COCR + HO —> ch, coon + RCO + NH —* REMAN, + HOE S qa cock + Ha CHycooH + HU 5 ca ° _ wt an ba as Cs Ae “@ 4 : _ _ a ett ee ee tL —R- cL ee RNA Pani mm im “hones on... 2 . ine “™ rf 2° Amide Tet Amide Ter west —v adap om fea = @ NH o . 3" Amide Fier cock 4 RAN ote + he ¥ eg Ester ete a tee ae ns rn: Akohol Phenol + Alkaline soln {oa [Neat] i ? oO CH, COCR +1HO-CHLCHs —» CHye-0-CsCH + HOE cr, coee + HO-O) —> cHyc- oO) + He , of GP of eo 6 ta gt eh ot wg abt age! +AU ; rag fon y to io aN # “aie Except + 1) Alkene told, (0: 2) 1° Aleohe) “26222 *H:5t, Heat & pistily @ an hydrolysis @ All. halogeno alkane reactions Levee! Nt | Oy + Madu Diol Aldehyde * 420 ® Esterification Reagents of oxi. reaction [tot /cotd] © Krinds,, 4 H:S04 —— Alkene C dilute) Alcohol (2) kez Cr,0q + Hay < Coitute) Aldehyde @ HNO, — Ketone Reagents of red. reaction Aldehyde © NaBH, in elhano) Lee [Needs heerting } Carboxyli¢ adi, @)LiATA, in x dry ether Nitrile cat] 
