Organic Reagent H20/H* Hg(OAc)2; NaBH./H20 BH3; H202/NaOH Ha, Pd/C, BaSO4 Na, NH3 NaNH2 Mg/THF NH2NH2, KOH Zn-Hg, conc. HCl NagCr207, HCl Organic Reagent Function Reduces an alkene to an alcohol, rearrangement is possil Reduces an alkene to alcohol via markovnikov addition, rearrangement is not possible. Reduces an alkene to alcohol via anti-markovnikov addition, rearrangement is not possible. Reduces an alkyne to cis-alkene. Reduces an alkyne to trans-alkene. Takes a proton from terminal alkyne. With alkyl halide, it forms Grignard reagent. Reduces carbonyl compound to an alkane in basic condition Reduces carbonyl compound to an alkane in acidic condition. Substitutes the alkyl chain on the benzene ring with carboxylic acid group. It also oxidises alcohol and carbonyl compound to id carboxylicWwW 12. 13, 14, 15, 16, 17. 18. NaNOz, HCI, 0°C AIBN AlBrs AlCl BFR BH3 Bro CHeNa Turns primary amine to diazonium salt Itis free radical initiator. Upon heating it decomposes to give nitrogen gas and two free radicals. Itis lewis acid, useful in promoting electrophilic aromatic substitution both in bromination of aromatics and also in Friedel Crafts reaction. Itis a strong lewis acid, used to promote reaction such as chlorination of aromatic compounds, as well as Friedel Crafts reaction, also be used in MPV reaction, Itis a strong lewis acid and is commonly used for the formation of thioacetals from ketones or aldehydes with thiols. The product is a thioacetal. It is a reagent for hydroboration of alkenes and alkynes. It is also mentioned as BsHs. Bromine will reacts with alkenes, alkynes, aromatics, enols and enolates, producing brominated compounds. In the presence of light, bromine will also replace H atoms in alkanes. Finally, it is used to promote the Hoffmann rearrangement of amides to amines. Diazomethane is used to convert carboxylic acids into methyl esters and in Wolff rearrangement as a means of extending carboxylic acids by one carbon.19. 20, 21, 22, 23, 24, 25. Ch cN- crO3 ‘CuBr cucl cul Dec Itis a very good electrophile, it will react with multiple bonds as well as aromatics, enols and enolates to give chlorinated products. in adcition, it will substitute Cl for halogens when treated with light (free radical mechanism). Finally it assist with the Hoffmann rearrangement of amides to amines. It is good nucleophile for substitution reaction used to form cyanehydrins. It also catalyse the benzoin condensation It is an oxidising agent for alcohols. its strength depends upon the additives present, In presence of pyridine, it will oxidise primary alcohols to aldehyde, as well as secondary alcohols to ketone group and in presence of acid, primary alcohols and acid directly. aldehydes are oxidised to carboxyl It is used in Sandmeyer reaction where an aryl diazonium salt is converted to an aryl bromide. Ocassionally, it is also used for preparation of organocuprates. It is used in Sandmeyer reaction and for the formation of organocuprates. It is used to form organocuprates, i , Gimann reagent, when two equivalents of organolithium reagents are added, Dieyclohexyl carbodiimide is a reagent used for the synthesis of amide from amines and carboxylic acids. itis essentially a reagent for dehydration.26. 2. 23, 30, 31 32, 33, Des-martin periodinane DIBAL-H FeCh Fe FeBrs Gilman reagent Grignard reagent Hy Its an oxidising agent It wil oxidise primary alcohels to aldehydes without going to carboxylic acid, i isobutyl aluminium hydride is a strong, bulky reducing agent It is mostly used for partial reduction of esters to aldehydes. It will also reduce amides, aldehydes, ketones and nitriles, Its a lewis acia, It is useful in prometing the chiorination of aromatic compounds with Cla, as well asin Friedel Crafts reaction, It will reduce nitro group to amine in presence of an acid, ie., Ha. It is a lewis acid. It is useful in promoting the bramination of aromatic compounds with Bra, as well as in Friedel Crafts reaction, (Organocuprate reagents are carbon nucleophiles. They will do 1,4-addition to o,8-ursaturated ketones as well as Sy? reaction with certain types of alkyl halides. They also add to acy’ halides to give ketones. ‘They are extremely good nucleophiles and strong bases. They react with many electrophiles containing a cerbony! group 4, aldehyde, ketone, ester, CO:, epoxides, Its used for reduction of alkenes, alkynes and many other species with muttiple bond, in concert with catalyst such as A/C, Ni, PL35, 36. 37, 38 39, HCO, H.02 80, Her HCI Hg(OAc), ‘Chromic acid is a strong acid and an oxidant. It will oxidize secondary alcohols to ketones and primary alcohols to - ‘COOH. It is sometimes generated by using K2Cr20; in the presence of a strong acid. Its preferred oxidant in hydroboration oxidation reaction, ‘which results in the formation of alcohols vis anti- markovnikov addition, It oxidises aldehydes to carboxylic acid, This is seen in its use for the oxidative workup in ozonelysis. Its astrong acid, Its particularly useful as an acid for elimination reaction, since the conjugate bese is a very poor nucleophile. itis used in many other reactions simply asa strong acid. Its a strong acid, It can add to compounds with multiple bonds forming brominated compounds, also reacts with primary, secondary and tertiary alcohols to form ally! bromides, Its astrong acid, Itcan add to compounds with muttiple bonds forming chlorinated compounds, also reacts with primary, secondary and tertiary alcohols to form aly! chlorides. Mercurie acetate is a useful reagent for oxymercurration of alkenes and alkynes. it makes double bond more reactive ‘towards nucleophilic attack by nucieaphiles such 2s H2O and alcohols. “The Hg is removed using NaBH, or H»SO,, this step is called as demercurration. Mercuric sulphate is a lewis acid, In the presence of aquecus acid, HO", It perform oxymercurration of alkynes to ketones,a 43, 45, a. HI HIOs HNO, HNO; KOC(Me)s Iisa strong acid, It can ade to compounds with multiple bonds forming iodinated compounds, also reacts with primary, secondary an tertiary alcohols to form alkyl iodides, Periodic acid is an oxidant that is useful for the cleavage of 1,2-fols (vicinal ols) to form aldehydes and ketones, Nitrous acid is primarily used to convert aromatic amines to clazonium saits, itis sometimes represented as NaNO + HC) at orc, Nitric acid is a strong acid, tt will add NO3 to aromatic compounds in presence of conc, H,S0, It also oxidises Primary alcohols and aldehydes to carboxylic acids. It is a good eectrophile, Itwill react with carbon-carbon multiple bonds such as alkenes and alkynes along with other nucleophile. itis a very strong axédising agent. tt wil oxidise primary alcohols and aldehydes to -COOH and secondary slechols to ketones, form iols from alkenes and oxidatively cleave C-C multipie bonds, Potassium tert-butoxide is a strong sterically hindered base. It is the prototypical bulky base, useful for forming less substituted alkenes in efimination reaction. Lithium diisopropylamide is a strong, bulky, non-nucleophilic base, tis the reagent of choice for selectively removing a Proton from the least hindered carbon next to a ketone. It can also be used to form the Hoffmann product in E3 reaction.49, 50, 51, 532, 53, 55, 36, LAIHTOC(Me):] UAIHs Lindiar catalyst m-CPBA Mes Mg Msc It is a metal reducing agent, similar to Na and K, although ‘weaker It can convert alkyl halides to alky! lithium ‘compounds. It also form alkoxides from alcohols and reduce aromatic groups. Itis astrong and bulky reducing agent, which ‘than LiAIH, less reactive Itconverts acyl halide to aldehyde, Lithium aluminium hydride is. very strong reducing agent. It Feduces aldehyde, ketone, ester and carboxylic acid into alcohols. It also reduces amides & nitriles to amines, It also ‘open epoxides, Itis a poisoned pallagium metal catalyst that performs partial hydrogenation of alkynes in presence of H; gas. It always give tthe cis-alkene, in contrast to Na/NHs, which gives trans- alkene Meta-chioroperoxybenzoic acid is an oxidising agent. its main luse is in the formation of epoxides from alkenes. It also oxidise ketones te form esters, a reaction known as Bayer Villiger reaction. Dimethy! sulphide fs used in the reductive workup for ‘ozonolysis, especially one wants ta obtain aldehydes from alkenes, It reduces the ozonide formed, leading to the formation of dimethyisupfoxide (DMSO). Its used in the formation of Grignard reagents from allyl and alkeny! halides. Methane sulphony! chloride (Mesyl chloride) is used to tum alcohols into good leaving groups. It behaves identically to ‘SCI {Tasy! chloride} for this purpose.57. 58 59, 61 62 63, 65, Na NaBHiOAchy NaBH, NaCNBH; NaH Nala, NaN NaNH NBS tis strong reducing agent. it-will reduce alkynes to trans- alkenes and form hydrogen gas when added te alcohols, forming alkoxides. Its also used in Birch reduction of aromatic groups Sodium triacetoxy borohydride is 8 reducing agent for reductive amination of ketones and aldehydes to amines. It is Identical to NaCNBH, Sodium borohydride is a reagent for the reduction of ketones and aldehydes, It will also reduce acie halides. It is also used in oxymercuration reaction to replace mercury with H. Sodium qyanoborohydride isa reducing agent. Its used for reductive amination of imines to amines. It preform this reaction under slighty acidic concition. Sodium hydride is 2 very strong base and a poor nucleophile, It is useful for éeprotonating aleahols and alkynes, among others, One advantage is that by-product is Ha, which is @.gas, and ir escapes easily. Sodium periodate is a strong oxidant. it Geaves 1,2.diois to give aldehyde and ketones, (Refer SNo, 42) Sodium azide is 2 good nucleophile that will participate in Sy? reaction, Sodium amide is a very strong base, useful fer deprotonation af alkynes and in elimination reaction towards the fermation of alkynes from aihalides. It can also be used to generate arynes, which can undergo nucleophilic attack. N-Bromosuccimide is 2 source of reactive bromine, it is most aften used fer allylic bromination and used for the formation of bromohydrin from alkene,6, 70, m1. 72. TR 74 NCS NH2NH> NH NB NS. Oo on Organciithium reagents N-Chlorosuccimide is a source of reactive chlorine, It is most often used fer allylic chlorination and used for the formation of chlorohydrin from alkene, Hycrazine is 2 good reducing agent and also works as 3 nucleophile. I is used in converting ketones to alkanes, i, Wolff Kishner reduction. Its also used in the final step of Gabriel Phthalimide synthesis to liberste primary amine. Hydroxylamine is used in formation of aximes from aldehydes and ketones, The resulting amines can be converted into amides using Beckmann rearrangement. Ammonia is a base and a nucleophile, itis often used as @ solvent in reaction involving Li, Na and K, has low boiling point. Nicket boride is a reagent that acts similarly to Lindlar catalyst, reacting with alkynes te give cis-alkenes, N-lodosuccimide is @ source of iodine similar to NBS and NCS. When added to an alkene in presence of water, it will form lodohyarin, Ozone will cleave alkene and alkynes to give carbenyl compounds. The products forms will depend on the type of workup used, whether oxidative or reductive. Reductive workup preserve aldehyde whi oxidative workup will oxidise any aldehyde to carboxylic acid, Itisastrong base and a good nucleophile, They are extremely strong bases and good nucleaphiles. They react with carbonyl compounds and epoxides. Being strong base, they also react with groups containing acidic hydrogen.1. 16 78, 81 P05 PRAOAC) Pers PoC Poh POs POC Sodium oF Potassium: Phthalimide ols Osmium tetracxide is @ reagent for the formation of 1,2, from alkenes. The selectivity for this reaction is always syn. It is a dehydrating agent: It is used for the conversion of carboxylic acid to anhydride and also forthe formation of nitrile and amige. Lead tetraacetate will cleave 1,2-ciols into aldehydes or ketones, similar to NalO4 and HIO4, (Refer SNo.42 & 62) It is used to convert alcohol to alkyl bromide, also: convert carboxylic acid to acid bromide ar acyl bromide, Pyridinium Chloro Chromate is a reagent for the oxidation of primary alcohols to sldehycles and secondary alcohols to ketones, itis much milder oxidising agent as compared to H2CrO4and KMnO4, It is used to convert alcohol to alkyl chloride, also convert foride, carbonylic acid to acid chloride or acy! Its used to convert alcohol to alkyl chloride, also convert arid, carboxylic acid to acid chloride or acy! Palladium adsorbed on charcoal is a heterogenous catalyst. In presence of H; gas, it convert alkenes and alkynes to alkanes, The selectivity for the reaction is syn. Phosphorous oxychloride is used for the dehydration of alcohols to alkenes, Essentially, it converts alcohols to good leaving group, which is then removed by an added base, often pyridine, itis used to convert amides to nitriles. Its aritrogen containing nucleophile used in Gabriel Phthalimide synthesis It reacts with alky| halide to form a C-N bond, which is then hydrolysed by treatment with hydrazine to give primary amine,85, 87, 83, 1 92, 33, PPhs Pyridine Raney-Ni ROOR AgNO) Sn. 503 {tis used for the formation of ylides in Witting reaction. It is also used for the reduction in ozonolysis of alkenes, Platinum is@ roble metal. itis used as a catalyst for the. reduction of C-C multiple bonds in the presence of Hy gas. Pyridine is a mild base. Since it ‘s neutral, so itis soluble in organic solvents, Its often used in reaction that generates HCl and other strong acids - think of it like a sponge for strong acid. Its @ reagent for hydrogenation of double bonds, also used as a replacement of sulphur by hydrogen, Peroxides are used to initiate free radical reactions, The 0-O bond is very wealc and will fragment homolytically to generate radicals, It reacts with alky! halide to form Agy and the corresponding carbocation. Its used in tollen’s reagent (reaction) to oxicise aldenyde to carboxylic acid, This is the basis of a test for the presence of aldehyde functional group when silver mirror daposits Gown, lis commonly used as @ base for Hoffmann elimination of quaternary ammonium salts, In the presence of acid, tin will reduce nitro group to form amine. Its used for sulphonation of aromatic groups in the presence of acid, Thiony\ chloride is used for the formation of alky! chioride from alcohols and acid chloride from carbonylic acid,95, 7, 100. 101, 102, 103, 104. TRAF TMSCI scl p-TSOH Zn-Cu MMPP Zn-Hg Bayer's reagent Collins reagent Tetra n-buty! ammonium fluoride is @ source of fluoride fon, used to cleave silyl ethers which are common protecting groups for alcohols, Timethy! silyl chioride is 2 protecting group for alcohols. When added to alcoha’s, it forms a silyl ether, which is inert to most reagents except for Fluoride fon and acid, Tosyl chloride (Toluene sulphony! chloride) is used to convert alcohols to -OTs group, which are excellent leaving groupin elimination and substitution reactions, Para-Toluene sulphonic acid (Tosic acid) is a very strong acid. Its conjugate base is @ very pocr nucleophile, which makes it a good acid for elimination reaction. Its reducing agent, useful for reduction af azonides and also In reduction of nitre groups to amines in the presence of an add, Zine-Copper couple is a reducing agent, used to form carbenes, actualy carbenoids, from aikyi dihalides, when this is added to alkenes, they form cyclopropanes. Magnesium monoperoxyphthalate hexahydrate forms epoxides. In the presence of an acid, zinc amalgam will reduce ketones to alkanes, :e,, Clemmenson reduction, It isan alkaline solution of potassium permanganate (KMNO4), Used in organic chemistry as a qualitative test for the presence of unsaturation such as dauble bonds. Used to selectively oxicise primary alcohols to an aldehyde.106. 107 10 m, 12, va Fobinift agit Farts reaped Millon seagent smiz ent ction ee eve, 2a-cu Kye Hi Dee Martin Perinsinane i charieal reagent used ts exiin primary alcohols to ales aed secondary atcabals 19 etones, It inusee to cfr eriate Between water sohublealiehyse and hotanehinesional groups phot aldehyde pve pautive bast whe sremati aldehyde ess not Febling regent contin ti fren slain i Fein han Feng B Febiing fe Cus 5H.0 Febing Sd Pasi Tarist Tethys sk fachele's ast Ie ies slain of 1202 ond ferous ulphate, eration act as casiptand prerttes the formation offre aca is sed to edie contaminants ot waste water It suid to ate seganieeoreuna, se anal eigent used 99 deter whe presence’ of sible protein, Fink icon a we! oa pany esha ts aldehyde and secondary alo to ketones ais un 3¢ Confer ragent Svar ogi i an organic commpoun. ten employed as 2 soluton Far angie ayes ts inane Koga’: songent. is» powell neucing agent aloe eoiian af expr carnlened wih irate fan ned to detest alee Special ing gio ot aco Forms cyclopropane fing at ahene i Simmons-Smith It inuues or a halagenaton in carzanle aids The ame of the resction if HVZ easton.