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Reagent List

The document provides an overview of various chemical reagents and their applications in organic chemistry, including oxidation, reduction, and substitution reactions. Key reagents discussed include Silver Oxide, Aluminum Chloride, Borane, Bromine, and Lithium Aluminum Hydride, each with specific roles in reactions such as the Tollens' test, Friedel-Crafts reactions, hydroboration, and reductions of various functional groups. The document also highlights the mechanisms and outcomes of these reactions, emphasizing the importance of these reagents in synthetic organic chemistry.

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19 views13 pages

Reagent List

The document provides an overview of various chemical reagents and their applications in organic chemistry, including oxidation, reduction, and substitution reactions. Key reagents discussed include Silver Oxide, Aluminum Chloride, Borane, Bromine, and Lithium Aluminum Hydride, each with specific roles in reactions such as the Tollens' test, Friedel-Crafts reactions, hydroboration, and reductions of various functional groups. The document also highlights the mechanisms and outcomes of these reactions, emphasizing the importance of these reagents in synthetic organic chemistry.

Uploaded by

gpfcb65786
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF or read online on Scribd
1.g,0 Silver Oxide Silver oxide is used in the Tollens’ reagent for oxidizing aldehydes to carboxylic acids: ARO, HO. Oo? Mor H,c>— * AB Like other aldehydes, aldoses(For Example Glucose) react with ‘Tollens’ reagent giving the positive test. HL i HOS 6, HOH G@agonnon — H—}—0H oe ir” OH—|—H_ + AgL H H—|——on a —|—0n (on ‘© Ketose (for example fructose) can also give tollen’s test Because in basie medium it will converted into aldose: © Reducing sugars -Sugars that give positive tests with ‘Tollens” or Benedict's or fehling’s solutions are known as reducing sugars, [Link], Aluminum Chloride # AICI, (or we can use AIBr, )is a strong Lewis acid used as a catalyst in Friedel- Crafis Reaction and other Electrophilic Aromatic Substitution reaction Alkylation In this reaction Carbocation intermediate i formed (please do remember to rearran if possible) Acylation COR RcO-cI ‘Anhydrous AICI, [NO rearrangement because acytium cat is stabilized by back bonding (a special ‘ease of resonance) [Link],(B,H,) Borane (diborane) 18s used inthe hydroboraton-oxidation reactions of alkenes and alkynes. 1. InAlkenes Akene form Aleohol by anteMarkovnikov addition of water PB on, NH HCO SCH Goaxon HAC 2 InAllynes Alkyne form Carbonyl Compound by anti-Markovnikov ‘addition of water followed by tautomerization, = NP ey Ol HC OKO a ne7Sen, We can also use diborane with THF (Tetra Hydrofuran solvent), The role of THF is used to break dimer BH, ‘To prevent addition of BH, to the second x bond of the alkyne, CuBr We can also use CuCl or Cul [Link] Dimethyl sulfide 1. used in the reductive ozonolysis of alkenes 2. Carbonyl compounds are formed pte ow * ee 2HCHO Hc ogea, MAL AL Me,S Hse. CH _o,+cc ~~, CH,CHO+HCHO Me,S Me,S C OFC 3 —" 9. CH,N, Diazomethane 1, Methyl-esterification of earboxy © CH,N, wey on 2 Cyelopropanation of alkenes CH, lic acids ° Hee o—CHs a4 Hye Sot, 2 gc" 3. Insertion of methylene into OH bond of phenol oH 10. DIBAL-H Reduction of Esters to Aldehydes Powe [Link]-H Hye ‘o-cH, 2-H,0 eT SN 0 Reduction of Nitrile to Aldehydes [Link]-H He 2.H,0 Hyco “H [Link] tron 1. Conversion of nitrobenzene into anitne Sxp-2 NH FelHCI ‘We can also use Sn HCI, H,+Ni,P4Pd in ethanol er Br/Fe 12.H, Hydrogen Hydrogen s with metal catalysts such as Pd, Pt, Nifor the reduetion of alkenes, alkynes and other functional groups containing x bonds. 1. Reduction of Alkenes and alkynes to alkanes Dihydrogen gas adds to alkenes and alkynes in the presence of finely divided catalysts lke platinum, palladium o nickel to form alkanes, This process is called hydrogenation. H,Ni or Pt or Pd eS yee, HINior Ptor Pad Seu Hd Hye Sen He cy 2. Reduction of Atkynes to alkenes + CisAlkene cry Hypa /—\_ Hye ts HPS or BaSO, Cis-2-Hexene Partially deactivated palladised charcoal isknown as Lindlar’s catalyst. + Trans Alkene alkynes on reduction with sodium in liquid ammonia form trans alkenes, Hs, Na/Liq NH. Sts tye Rte Naa Ng ‘Trans-2-Hexene 3. Reduction of a Cyanide to Amine + Nitriles on reduction with catalytic hydrogenation produce primary amines + This reaction is used for ascent of amine series, ie, for preparation of amines containing one carbon atom more than the starting amine ~~ _H2+ NiPLPd ae NH Hye’ 4. Catalytic Hydrogenation of Benzene Under vigorous conditions, ie, at high temperature and/ or pressure in the presence of nickel catalyst, hydrogenation of benzene gives eyelohexane O*-O 13.H,0* Acidic Hydrolysis. 1. Hydrolysis of Cyanide H,0" yo SS we) ° 2. Hydrolysis of Acid Derivatives + Hydrolysis of Acid Chloride al 9 wo OA — — 2 ic ‘OH + Hydrolysis of Anhydride Hac ° 9 9 fi pee > dig He ye ben ya 3. Hydrolysis of isocyanide H,0° — > chy —NH} + HCOOH he CHI 14. HX Hydrohalic acid ( X= CI,Br,!) 1. used in the addition reactions of alkenes and alkynes + Reaction of HX with Alkene In this reaction carbocation is formed , check the possibility ‘of rearrangements like hydride shift, methyl shift ring ‘expansion and ring contraction CH CH HC’ ‘CHy ge’ tects HBr Hye” 7 cH hye CH Gls Hs AAte HBr ts HC Hac Br + Reaction of HX with Alkyne Hy Agen 2HBr Hac’ ZO hc ar” Sar + Reaction of HBiperoxie with Alene to anti-markovnikov’s Peroxide effect or Kharasch effect is ap CH, Aft Hye" ble to HBr only HBr Peroxide 2. used in the substitution reactions of primary, secondary; and tertiary alcohols. In this reaction carbocation is formed . check the possibility of rearrangements like hydride shift , methyl shift ring SS G-G [Link](OAd), Mercuric di-acetate ‘© Is used in the Oxymercuration-Demereuration reaction of alkenes ‘& Alkenes into alcohols following the Markovnikoy’s rule CH. Hse on Hg(OAc),/H,0 NaBH, on yet, HORAN. ewe tse NaBH, ‘© Is used in the Alkoxymercuration-Demercuration reaction of alkenes '® Alkenes into Ethers following the Markovnikay’s rule, Wen, H9(OA0 MeOH, cy Hc’ NaBH, Hy CHs cH Hg(OAc),JMeOH ne SO NaBH, ec Gy Ho CH 16. HgSO, Mercurie Sulfate + It is used in conversion of alkynes to ketones, dil HgSO, ge He CH, Hye rl HgSO, “GLH,s0, [Link], Periodic acid + used for the oxidative cleavage of Cis-1,2-diols (vicinal diols) forming aldehydes and ketones. a ° BC, CH HI0, a —— HoH OH OH used for the oxidation of a-Hydroxy ketones forming carbonyl compound and carboxylic acid 7 wo kg eH He, cH ; a He" ono 4 used for the oxidation of ar 4y07 NH, 8, Reduction of Epoxides to Secondary Alcohols HC, LiAIH, Hyco ~CHs ‘0 9. Reduction of N ries (o Primary Amines Lithium tri tert-butoxy alu Itisa bulky reducing agent 4 Not as reactive as LiAIH, # It is used for reduction of acid chlorides and ester 10 aldehydes, 9 Hse HC H 24. MCPBA m-chloroperoxybenzoic acid 1. It is an oxidizing agent most commonly used for the O> cea O Anti-Dihydroxylation of Alkenes with MCPBA ‘MCPBA OH #0" a "OH 2. Inthe Baeyer-Villiger reaction ‘convertion of aldehydes and ketones to carboxylic acids and ‘esters respectively 25. Na/[Link], Sodium 1, Sodium isa very reactive metal that works as an electron donor and thus a reducing agent 2. tis used in Birch reduction 1. Birch reduction + Reduetion of internal alkynes to trans alkenes No/[Link], CH HyC- CH HyC' + Reduction of benzene O==0 ‘© Reduction of Substituted benzene with Electron ¢ Reduction of Substituted benzene with Electron withdrawing Groups Ox L0H Ox 0H & Na/[Link], és 26. NaBH, Sodium borohydride 1. NaBH, is mild reducing agent 2. its not so reactive and can be used to reduce aldehydes, ketones and acid halides + Reduction of Aldehyde into primary alcohol od + Reduction of Ketone into secondary aleohol CH NaBH, Hye’ ° On + Reduction of Acid Chloride into Primary aleohol ‘+ NaBH, isalso used inthe Oxymercuration-Demercuration reaction + NO rearrangement + Addition of water according to markovnikov's rule CH CH (Z0He _ NaBH, CH HC’ te On 27. NaNH, ‘Sodium amide 1. It is a very strong base most often used for preparing and nn—& CH ‘CH 3. In the Reduction of an Alkyne to a Trans Alkene ‘Trans alkenes are prepared by reducing internal alkynes by dissolving Na or Li in NH, Hc —===—cor, Lorna NH, —_ cH 33. NH,NH, Hydrazine 1. Itis a good nucleophile and a reducing agent 2. used in theWolff-Kishner reaction for conversion of Carbonyl compounds to alkanes, + In the Wolf © seaeed with OK Scanner NGH, KOH/heat ethylene glycol [Link],B Nickel boride 1. Nickel boride, a P-2 catalyst, sa reducing agent similar to the Lindlar’s catalyst 2. used for converting alkynes to cis alkenes. + Alkyne to Cis Alkene ¢ Et Li wo, cul wer, 35.0, Ozone 1, Iris an oxidizing agent used in the ozonolysis of alkenes and alkynes. 2. The ozonolysis of alkenes produces aldehydes or ketones when dimethyl sulfide or Zn is used (Reductive ezonolysis) 3. The ozonolysis of alkenes produces Carboxylic acid when, “water or Hydrogen peroxide is used, (Oxidative ozonolysis) 4, The ozonolysis of alkynes produces alpha dicarbonyl ‘compounds when dimethyl sulfide or Zn is used (Reductive ‘ezonolysis) The ozonolysis of alkynes produces carboxylic acids when ‘water or Hydrogen peroxide is used. (Oxidative ozonolysis) + Reductive Ozonolysis of Aikenes Zoe O;4CCl, g we Znorwe,S” nee + HCHO ive Ozonolysis of Alkenes ©. 9 oO 0,4CCI, Soy HO or H,0, by by + Reductive Ozonolysis of Alkynes He 8 cn, OstCCle yh ZnorMe,S / \y, ls tive Ozonolysis of internal Alkynes o,sCcl, H,0 or H,O, Oo HO wo = K OH He Oo + Oxidative Ozonolsisof terminal Alkynes WAS 01800 H,0 or H,0, 9 ak Hac’ ‘OH ners HC’ + CO,#H,0 36. PBr, Phosphorus tri bromide IL It is used for converting alcohols to alkyl bromides and ccarboxylicaeids to acid bromides. + carboxylicacids to acid bromides. a PCI, AA, ne oH ——> H.C’ 37.P,0, Phosphus pentoxide 1. Itis a dehydrating agent 2 used for converting carboxylic acids to anhydrides, and amides to nitriles respectively. + Conversion of carboxylic acids to anhydrides si A, Hye OH 67 0 cy + Conversion of amides to nitriles 9 A, HyC™ NH, P,Os HC: 38. PCC Pyridinium chlorochromate 1, Iisa mild oxidizing agemt 2. converting primary alcohols to aldehydes and secondary aleobols to ketones. + Conversion of primary alcohols to aldehydes PCC Hjc~ OH ——— oN + Conversion secondary alcohols to ketones Hy CH ron Ee woo 39. POCI, Phosphorus oxychloride 1. Isa dehydrating agent 2. used for converting alcohols to alkenes and amides to nitriles. + Alcohols to alkenes by POCI, OH O = O + Amides to Nitriles by POCI, Hye ° POCl, — He Hee SNH 40. Ph,P Triphenylphosphine 1. Mia mod for propaing Witig reagent Hye ar Saini Hye Sp Pg Further iti used to prepare alkene 9 A, Hac CH we CHy Hye SP hg CH 44,R,CuLi Organocuprates 1. Organocuprate reagents, also known as Gilman reagents 2. Used for preparation of alkanes and conjugate (1,4) addition 10.0, Prunsaturated carbonyls + Corey house synthesis - Preparation of Alkanes —_—_5, acu ReRI+ RCu + LiCl CI must be 1° Halide for better yiold + Conjugate Addition to a, f-unsaturated carbonyl campronds 9 ° Wore, Se en 45, Ra-Ni Raney Nickel 1. It is a reducing agent that is used most commonly for converting thio acetals to alkanes, 2. agood way of converting aldehydes and ketones to alkanes. + Carbonyl to alkane o [SH [\ who, — —- Xe ‘CH + Alkene to Alkane Hse Sets aN = Ho CHy 46.50, Sulfur trioxide 1. Its used for the sulphonation of aromatic compounds - 7 1 o=$=0 Oleum 2. The sulfonylation is reversible process ie. the SO,H ean be removed if treated with acid. It is used for blocking the position Ht oH cl, cs, o=9=o oH HO Ho cl a H,0* Heat [Link], Thionyl chloride 1. Itis @ chlorinating agent used for converting alcohols to ‘alkylehlorides and carboxylic acids to acid chlorides. + Conversion of alcohols to alkyl chlorides CH oH soc [- & | _* Pyridine #74 ‘SN? | CH CH CH SOC, | a SN’ CH, ‘+ Conversion of carboxylic acids to acid chlorides 0 0 socl, He te" on a [Link] Tin 1. tis a reducing agent used, in the presence of an acid + conversion of nitro group into an amine, sy? NH OQ SnlHCl O 49.7sCl p-Toluenesuifonyl chloride 1. Iris used for converting alcohols into alkyl sulfonates called tosylates (OTs) which isa good leaving group. 2. Tosylates ean then be used in substitution and elimination revetions + Substitution Reaction on OTs AK ra | Hac Hs = Hs i Nacn 7H CH Sh [Link] H,¢: oH Elimination Reaction on ots Hee Hy Hse CH HsC—0" Na” = Hc, Ey Notice that the stereochemistry ofthe aleohol is retained tosylating step, butt will change in an 8,2 reaction inthe

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