In this post, you will find the list of more than 100 important organic reagents and their function presented in a convenient tabular format. This format allows for easy readability and ensures a clear understanding of the information provided.
What is Organic Chemistry?
Organic chemistry is the branch of chemistry that involves the scientific study of organic compounds, i.e., compounds that contain covalently bonded carbon atoms. This branch of chemistry primarily deals with the structure and chemical composition of organic compounds, the physical properties and the chemical properties of organic compounds, and the chemical reactions which these organic compounds undergo.
The term ‘organic’ was coined because the field of organic chemistry was initially finite to compounds that were produced by living organisms. This was attributed to some ‘vital force’ that was present in organic substances as they had something that inanimate substances lacked. The above theory was debunked when Urey Miller synthesized urea from inorganic substances but the classification is still in use.
Organic chemistry is a vast science due to one key property exhibited by the element carbon, which is called carbon catenation. Carbon has the exceptional ability to form very stable bonds with other carbon atoms, giving it the ability to form stable molecules with relatively complex structures. Catenation is the ability of an element to form bonds with an atom of the same kind. Hence, the vastness of organic chemistry can be attributed to this property of carbon.
The importance of organic chemistry in the present age is as immense as it had been since its inception. It plays an important role in our everyday life because food, medicines, paper, clothes, soap, perfumes, etc are indispensable to us for proper living. The study of organic chemistry is important for chemists and pharmacists in synthesizing medicines for the alleviation of human suffering.
The reactions in organic chemistry occur between organic compounds. Let us now study the different terminologies, classifications, field effects, types of reagents, the stability of intermediates, and properties in detail.
Reagents in Organic Chemistry
Reagents are the chemicals that we add to bring about a specific change to an organic molecule. They play a crucial role in organic chemistry reactions. In fact, any general reaction in organic chemistry can be written as a combination of reactants and reagents that lead to the desired transformation of the molecules. Reagents provide the necessary conditions and catalysis to facilitate the desired reactions. Without these carefully selected chemicals, it would be challenging to achieve the desired changes in organic molecules. Organic chemists rely heavily on the proper identification and utilization of reagents to ensure successful chemical transformations.
Substrate + Reagent → Product
Where the substrate is an organic molecule to which we add the reagent.
Let’s discuss some of the vital organic reagents in the field of Organic Chemistry. Understanding and utilizing these reagents is crucial for successful organic synthesis and reactions. Organic chemistry relies heavily on a wide array of reagents that allow chemists to transform one organic molecule into another. These reagents serve specific purposes and have unique chemical properties. Below, we will explore a few important organic reagents.
1. Grignard Reagents: These reagents are organomagnesium compounds that consist of a carbon-metal bond. Grignard reagents are widely used for carbon-carbon bond formation, making them essential in the synthesis of complex organic molecules.
2. Nucleophiles: Nucleophiles are species that donate a pair of electrons in a chemical reaction. They play a vital role in various organic reactions, such as nucleophilic substitutions and addition reactions. Common nucleophiles include alkoxides, amines, and thiols.
3. Oxidizing and Reducing Agents: Organic oxidation and reduction reactions are essential for the transformation of functional groups. Oxidizing agents, such as potassium permanganate and chromium trioxide, are used to increase the oxidation state of a molecule. Reducing agents, such as sodium borohydride and lithium aluminum hydride, are employed to decrease the oxidation state.
4. Lewis Acids and Bases: These reagents are involved in Lewis acid-base reactions, where electron pairs are donated and accepted, respectively. Examples of Lewis acids include aluminum chloride and boron trifluoride, while Lewis bases can be represented by ammonia and pyridine.
5. Catalysts: Catalysts are substances that increase the rate of a chemical reaction without being consumed in the process. They play a crucial role in organic synthesis by facilitating various reactions. Some commonly used catalysts in organic chemistry include palladium, platinum, and enzymes.
These are just a few examples of the many important organic reagents used in the field of Organic Chemistry. Understanding their properties and applications is vital for organic chemists to design and execute successful reactions. By leveraging these reagents effectively, scientists can unlock the potential to create new and innovative organic molecules that have practical applications in various industries.
Read More: Organic Chemistry Conversion Charts
Important Organic Reagents and their functions in Organic Chemistry
| S No. | Organic Reagent | Organic Reagent Function |
|---|---|---|
| 1. | H2O/H+ | Reduces an alkene to an alcohol, rearrangement is possible. |
| 2. | Hg(OAc)2; NaBH4/H2O | Reduces an alkene to alcohol via markovnikov addition, rearrangement is not possible. |
| 3. | BH3; H2O2/NaOH | Reduces an alkene to alcohol via anti-markovnikov addition, rearrangement is not possible. |
| 4. | H2, Pd/C, BaSO4 | Reduces an alkyne to cis-alkene. |
| 5. | Na, NH3 | Reduces an alkyne to trans-alkene. |
| 6. | NaNH2 | Takes a proton from terminal alkyne. |
| 7. | Mg/THF | With alkyl halide, it forms Grignard reagent. |
| 8. | NH2NH2, KOH | Reduces carbonyl compound to an alkane in basic condition. |
| 9. | Zn-Hg, conc. HCl | Reduces carbonyl compound to an alkane in acidic condition. |
| 10. | Na2Cr2O7, HCl | Substitutes the alkyl chain on the benzene ring with carboxylic acid group. It also oxidises alcohol and carbonyl compound to carboxylic acid. |
| 11. | NaNO2, HCl, 0°C | Turns primary amine to diazonium salt |
| 12. | AIBN | It is free radical initiator. Upon heating it decomposes to give nitrogen gas and two free radicals. |
| 13. | AlBr3 | It is lewis acid, useful in promoting electrophilic aromatic substitution both in bromination of aromatics and also in Friedel Crafts reaction. |
| 14. | AlCl3 | It is 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. |
| 15. | BF3 | It is a strong lewis acid and is commonly used for the formation of thioacetals from ketones or aldehydes with thiols. The product is a thioacetal. |
| 16. | BH3 | It is a reagent for hydroboration of alkenes and alkynes. It is also mentioned as B2H6. |
| 17. | Br2 | 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. |
| 18. | CH2N2 | 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. | Cl2 | It is a very good electrophile. It will react with multiple bonds as well as aromatics, enols and enolates to give chlorinated products. in addition, it will substitute Cl for halogens when treated with light (free radical mechanism). Finally it assist with the Hoffmann rearrangement of amides to amines. |
| 20. | CN– | It is good nucleophile for substitution reaction used to form cyanohydrins. It also catalyse the benzoin condensation. |
| 21. | CrO3 | 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 aldehydes are oxidised to carboxylic acid directly. |
| 22. | CuBr | 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. |
| 23. | CuCl | It is used in Sandmeyer reaction and for the formation of organocuprates. |
| 24. | CuI | It is used to form organocuprates, i.e., Gimann reagent, when two equivalents of organolithium reagents are added. |
| 25. | DCC | Dicyclohexyl carbodiimide is a reagent used for the synthesis of amide from amines and carboxylic acids. It is essentially a reagent for dehydration. |
| 26. | Des-martin periodinane | It is an oxidising agent. It will oxidise primary alcohols to aldehydes without going to carboxylic acid. |
| 27. | DIBAL-H | Di 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. |
| 28. | FeCl3 | It is a lewis acid. It is useful in promoting the chlorination of aromatic compounds with Cl2, as well as in Friedel Crafts reaction. |
| 29. | Fe | It will reduce nitro group to amine in presence of an acid, i.e., HCl. |
| 30. | FeBr3 | It is a lewis acid. It is useful in promoting the bromination of aromatic compounds with Br2, as well as in Friedel Crafts reaction. |
| 31. | Gilman reagent | Organocuprate reagents are carbon nucleophiles. They will do 1,4-addition to α,β-unsaturated ketones as well as SN2 reaction with certain types of alkyl halides. They also add to acyl halides to give ketones. |
| 32. | Grignard reagent | They are extremely good nucleophiles and strong bases. They react with many electrophiles containing a carbonyl group e.g., aldehyde, ketone, ester, CO2, epoxides. |
| 33. | H2 | It is used for reduction of alkenes, alkynes and many other species with multiple bond, in concert with catalyst such as Pd/C, Ni, Pt. |
| 34. | H2CrO4 | 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 K2Cr2O7 in the presence of a strong acid. |
| 35. | H2O2 | It is preferred oxidant in hydroboration oxidation reaction, which results in the formation of alcohols via anti-markovnikov addition. It oxidises aldehydes to carboxylic acid. This is seen in its use for the oxidative workup in ozonolysis. |
| 36. | H2SO4 | It is a strong acid. It is particularly useful as an acid for elimination reaction, since the conjugate base is a very poor nucleophile. It is used in many other reactions simply as a strong acid. |
| 37. | HBr | It is a strong acid. It can add to compounds with multiple bonds forming brominated compounds, also reacts with primary, secondary and tertiary alcohols to form alkyl bromides. |
| 38. | HCl | It is a strong acid. It can add to compounds with multiple bonds forming chlorinated compounds, also reacts with primary, secondary and tertiary alcohols to form alkyl chlorides. |
| 39. | Hg(OAc)2 | Mercuric acetate is a useful reagent for oxymercurration of alkenes and alkynes. It makes double bond more reactive towards nucleophilic attack by nucleophiles such as H2O and alcohols. The Hg is removed using NaBH4 or H2SO4, this step is called as demercurration. |
| 40. | HgSO4 | Mercuric sulphate is a lewis acid. In the presence of aqueous acid, H3O+, it perform oxymercurration of alkynes to ketones. |
| 41. | HI | It is a strong acid. It can add to compounds with multiple bonds forming iodinated compounds, also reacts with primary, secondary and tertiary alcohols to form alkyl iodides. |
| 42. | HIO4 | Periodic acid is an oxidant that is useful for the cleavage of 1,2-diols (vicinal diols) to form aldehydes and ketones. |
| 43. | HNO2 | Nitrous acid is primarily used to convert aromatic amines to diazonium salts. It is sometimes represented as NaNO2 + HCl at 0°C. |
| 44. | HNO3 | Nitric acid is a strong acid. It will add NO2 to aromatic compounds in presence of conc. H2SO4. It also oxidises primary alcohols and aldehydes to carboxylic acids. |
| 45. | I2 | It is a good electrophile. It will react with carbon-carbon multiple bonds such as alkenes and alkynes along with other nucleophile. |
| 46. | KMnO4 | It is a very strong oxidising agent. It will oxidise primary alcohols and aldehydes to -COOH and secondary alcohols to ketones, form diols from alkenes and oxidatively cleave C-C multiple bonds. |
| 47. | KOC(Me)3 | Potassium tert-butoxide is a strong sterically hindered base. It is the prototypical bulky base, useful for forming less substituted alkenes in elimination reaction. |
| 48. | LDA | Lithium diisopropylamide is a strong, bulky, non-nucleophilic base. It is 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 E2 reaction. |
| 49. | Li | It is a metal reducing agent, similar to Na and K, although weaker. It can convert alkyl halides to alkyl lithium compounds. It also form alkoxides from alcohols and reduce aromatic groups. |
| 50. | LiAlH[OC(Me)3] | It is a strong and bulky reducing agent, which is less reactive than LiAlH4. It converts acyl halide to aldehyde. |
| 51. | LiAlH4 | Lithium aluminium hydride is a very strong reducing agent. It reduces aldehyde, ketone, ester and carboxylic acid into alcohols. It also reduces amides & nitriles to amines. It also open epoxides. |
| 52. | Lindlar catalyst | It is a poisoned palladium metal catalyst that performs partial hydrogenation of alkynes in presence of H2 gas. It always give the cis-alkene, in contrast to Na/NH3, which gives trans-alkene. |
| 53. | m-CPBA | Meta-chloroperoxybenzoic acid is an oxidising agent. Its main use is in the formation of epoxides from alkenes. It also oxidise ketones to form esters, a reaction known as Bayer-Villiger reaction. |
| 54. | Me2S | Dimethyl sulphide is used in the reductive workup for ozonolysis, especially one wants to obtain aldehydes from alkenes. It reduces the ozonide formed, leading to the formation of dimethylsupfoxide (DMSO). |
| 55. | Mg | It is used in the formation of Grignard reagents from alkyl and alkenyl halides. |
| 56. | MsCl | Methane sulphonyl chloride (Mesyl chloride) is used to turn alcohols into good leaving groups. It behaves identically to TsCl (Tosyl chloride) for this purpose. |
| 57. | Na | It is strong reducing agent. It will reduce alkynes to trans-alkenes and form hydrogen gas when added to alcohols, forming alkoxides. It is also used in Birch reduction of aromatic groups. |
| 58. | NaBH(OAc)3 | Sodium triacetoxy borohydride is a reducing agent for reductive amination of ketones and aldehydes to amines. It is identical to NaCNBH3. |
| 59. | NaBH4 | Sodium borohydride is a reagent for the reduction of ketones and aldehydes. It will also reduce acid halides. It is also used in oxymercuration reaction to replace mercury with H. |
| 60. | NaCNBH3 | Sodium cyanoborohydride is a reducing agent. It is used for reductive amination of imines to amines. It preform this reaction under slightly acidic condition. |
| 61. | NaH | Sodium hydride is a very strong base and a poor nucleophile. It is useful for deprotonating alcohols and alkynes, among others. One advantage is that by-product is H2, which is a gas, and ir escapes easily. |
| 62. | NaIO4 | Sodium periodate is a strong oxidant. It cleaves 1,2-diols to give aldehyde and ketones. (Refer SNo. 42) |
| 63. | NaN3 | Sodium azide is a good nucleophile that will participate in SN2 reaction. |
| 64. | NaNH2 | Sodium amide is a very strong base, useful for deprotonation of alkynes and in elimination reaction towards the formation of alkynes from dihalides. It can also be used to generate arynes, which can undergo nucleophilic attack. |
| 65. | NBS | N-Bromosuccimide is a source of reactive bromine. It is most often used for allylic bromination and used for the formation of bromohydrin from alkene. |
| 66. | NCS | N-Chlorosuccimide is a source of reactive chlorine. It is most often used for allylic chlorination and used for the formation of chlorohydrin from alkene. |
| 67. | NH2NH2 | Hydrazine is a good reducing agent and also works as a nucleophile. It is used in converting ketones to alkanes, i.e., Wolff Kishner reduction. It is also used in the final step of Gabriel Phthalimide synthesis to liberate primary amine. |
| 68. | NH2OH | Hydroxylamine is used in formation of oximes from aldehydes and ketones. The resulting amines can be converted into amides using Beckmann rearrangement. |
| 69. | NH3 | Ammonia is a base and a nucleophile. It is often used as a solvent in reaction involving Li, Na and K, has low boiling point. |
| 70. | Ni-B | Nickel boride is a reagent that acts similarly to Lindlar catalyst, reacting with alkynes to give cis-alkenes. |
| 71. | NIS | N-Iodosuccimide is a source of iodine similar to NBS and NCS. When added to an alkene in presence of water, it will form iodohydrin. |
| 72. | O3 | Ozone will cleave alkene and alkynes to give carbonyl compounds. The products form will depend on the type of workup used, whether oxidative or reductive. Reductive workup preserve aldehyde while oxidative workup will oxidise any aldehyde to carboxylic acid. |
| 73. | OH– | It is a strong base and a good nucleophile. |
| 74. | Organolithium reagents | They are extremely strong bases and good nucleophiles. They react with carbonyl compounds and epoxides. Being strong base, they also react with groups containing acidic hydrogen. |
| 75. | OsO4 | Osmium tetraoxide is a reagent for the formation of 1,2-diols from alkenes. The selectivity for this reaction is always syn. |
| 76. | P2O5 | It is a dehydrating agent. It is used for the conversion of carboxylic acid to anhydride and also for the formation of nitrile and amide. |
| 77. | Pb(OAc)4 | Lead tetraacetate will cleave 1,2-diols into aldehydes or ketones, similar to NaIO4 and HIO4. (Refer SNo. 42 & 62) |
| 78. | PBr3 | It is used to convert alcohol to alkyl bromide, also convert carboxylic acid to acid bromide or acyl bromide. |
| 79. | PCC | Pyridinium Chloro Chromate is a reagent for the oxidation of primary alcohols to aldehydes and secondary alcohols to ketones. it is much milder oxidising agent as compared to H2CrO4 and KMnO4. |
| 80. | PCl3 | It is used to convert alcohol to alkyl chloride, also convert carboxylic acid to acid chloride or acyl chloride. |
| 81. | PCl5 | It is used to convert alcohol to alkyl chloride, also convert carboxylic acid to acid chloride or acyl chloride. |
| 82. | Pd/C | Palladium adsorbed on charcoal is a heterogenous catalyst. In presence of H2 gas, it convert alkenes and alkynes to alkanes. The selectivity for the reaction is syn. |
| 83. | POCl3 | 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. It is used to convert amides to nitriles. |
| 84. | Sodium or Potassium Phthalimide | It is a nitrogen containing nucleophile used in Gabriel Phthalimide synthesis. It reacts with alkyl halide to form a C-N bond, which is then hydrolysed by treatment with hydrazine to give primary amine. |
| 85. | PPh3 | It is used for the formation of ylides in Witting reaction. It is also used for the reduction in ozonolysis of alkenes. |
| 86. | Pt | Platinum is a noble metal. It is used as a catalyst for the reduction of C-C multiple bonds in the presence of H2 gas. |
| 87. | Pyridine | Pyridine is a mild base. Since it is neutral, so it is soluble in organic solvents. It is often used in reaction that generates HCl and other strong acids – think of it like a sponge for strong acid. |
| 88. | Raney-Ni | It is a reagent for hydrogenation of double bonds, also used as a replacement of sulphur by hydrogen. |
| 89. | ROOR | Peroxides are used to initiate free radical reactions. The O-O bond is very weak and will fragment homolytically to generate radicals. |
| 90. | AgNO3 | It reacts with alkyl halide to form AgX and the corresponding carbocation. |
| 91. | Ag2O | It is used in tollen’s reagent (reaction) to oxidise aldehyde to carboxylic acid. This is the basis of a test for the presence of aldehyde functional group when silver mirror deposits down. It is commonly used as a base for Hoffmann elimination of quaternary ammonium salts. |
| 92. | Sn | In the presence of acid, tin will reduce nitro group to form amine. |
| 93. | SO3 | It is used for sulphonation of aromatic groups in the presence of acid. |
| 94. | SOCl2 | Thionyl chloride is used for the formation of alkyl chloride from alcohols and acid chloride from carboxylic acid. |
| 95. | TBAF | Tetra n-butyl ammonium fluoride is a source of fluoride ion, used to cleave silyl ethers which are common protecting groups for alcohols. |
| 96. | TMSCl | Trimethyl silyl chloride is a protecting group for alcohols. When added to alcohols, it forms a silyl ether, which is inert to most reagents except for fluoride ion and acid. |
| 97. | TsCl | Tosyl chloride (Toluene sulphonyl chloride) is used to convert alcohols to -OTs group, which are excellent leaving group in elmination and substitution reactions. |
| 98. | p-TsOH | Para-Toluene sulphonic acid (Tosic acid) is a very strong acid. Its conjugate base is a very poor nucleophile, which makes it a good acid for elimination reaction. |
| 99. | Zn | It is reducing agent, useful for reduction of ozonides and also in reduction of nitro groups to amines in the presence of an acid. |
| 100. | Zn-Cu | Zinc-Copper couple is a reducing agent, used to form carbenes, actually carbenoids, from alkyl dihalides. When this is added to alkenes, they form cyclopropanes. |
| 101. | MMPP | Magnesium monoperoxyphthalate hexahydrate forms epoxides. |
| 102. | Zn-Hg | In the presence of an acid, zinc amalgam will reduce ketones to alkanes, i.e., Clemmenson reduction. |
| 103. | Bayer’s reagent | It is an alkaline solution of potassium permanganate (KMnO4), used in organic chemistry as a qualitative test for the presence of unsaturation such as double bonds. |
| 104. | Collins reagent | Used to selectively oxidise primary alcohols to an aldehyde. |
| 105. | DMP | Dee-Martin Periodinane is a chemical reagent used to oxidise primary alcohols to aldehydes and secondary alcohols to ketones. |
| 106. | Fehling’s reagent | It is used to differentiate between water-soluble aldehyde and ketone functional groups. Aliphatic aldehydes give positive test while aromatic aldehyde does not. Fehling reagent contains two different solutions, i.e., Fehling A and Fehling B. Fehling A: CuSO4.5H2O Fehling B: Sodium Potassium Tartrate Tetrahydrate aka Rochelle’s salt |
| 107. | Fenton’s reagent | It is a solution of H2O2 and ferrous sulphate. Ferrous ion acts as catalyst and promotes the formation of free radicals. It is used to oxidise contaminants or waste water. It is used to destroy organic compounds. |
| 108. | Millon’s reagent | An analytical reagent used to detect the presence of soluble proteins. |
| 109. | PDC | Pyridinium dichromate is used to oxidise primary alcohol to aldehyde and secondary alcohol to ketone. It is also known as Conforth reagent. |
| 110. | SmI2 | Samarium (II) iodide is an inorganic compound. When employed as a solution for organic synthesis, it is known as Kagan’s reagent. It is a powerful reducing agent. |
| 111. | Benedict solution | Alkaline solution of cupric ion complexed with citrate ion, used to detect aldehydes. |
| 112. | MnO2 | Special oxidising agent for alcohols. |
| 113. | CH2I2, Zn-Cu | Forms cyclopropane ring at alkene. It is Simmons-Smith reaction. |
| 114. | X2/Red P, H2O | It is used for α-halogenation in carboxylic acids. The name of the reaction if HVZ reaction. |
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Do comment down, if you have your own list of organic reagents for addition in this list.
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what do you mean by rearrangement possible/ not possible
rearrangement indicates example conversion of secondary carbocation to tertiary carbocation; ring expansion or ring contraction, etc
I need it in pdf format
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