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DAT OCHEM reagents and Lab tests
Terms in this set (30)
Silver oxide is used in the Tollens reaction to oxidize aldehydes to carboxylic acids. This is the basis of a test for the presence of aldehydes, since a mirror of metallic silver will be deposited on the flask. It is also commonly used as a base for the Hofmann elimination.
Silver nitrate will react with alkyl halides to form silver halides and the corresponding carbocation It can also react in the Tollens reaction to give carboxylic acids from aldehydes.
AlBr3 is a Lewis acid. It is useful for promoting electrophilic aromatic substitution, both in bromination of aromatics and also in the Friedel-Crafts reaction
Aluminum chloride is a strong Lewis acid. It is used to promote reactions such as chlorination of aromatic compounds, as well as Friedel-Crafts reactions.
Bromine will react with alkenes, alkynes, aromatics, enols, and enolates, producing brominated compounds. In the presence of light, bromine will also replace hydrogen atoms in alkanes. Finally, bromine is used to promote the Hoffmann rearrangement of amides to amines.
Chromium trioxide is an oxidizing agent for alcohols. Its strength depends on the additives present. When in the presence of pyridine, it will oxidize primary alcohols to aldehydes, as well as secondary alcohols to ketones. When acid is present, primary alcohols (and aldehydes) are oxidized to carboxylic acids
Grignard reagents are extremely good nucleophiles and strong bases. They react with many electrophiles containing a C=O (carbonyl) group such as aldehydes, ketones, esters, and carbon dioxide, as well as epoxides. Being strong bases, they are protonated by water, alcohols, carboxylic acids and other acidic species
Chromic acid is a strong acid and an oxidant. It will oxidize secondary alcohols to ketones and primary alcohols to carboxylic acids. It is sometimes generated by using K2Cr2O7 (or Na2Cr2O7) in the presence of strong acid
Sulfuric acid is a strong acid. It is particularly useful as an acid for elimination reactions, since the conjugate base is a very poor nucleophile. It is used in many other reactions simply as a strong acid.
Mercuric acetate is a useful reagent for the oxymercuration of alkenes and alkynes. It makes double bonds more reactive towards nucleophilic attack by nucleophiles such as water and alcohols. The mercury is removed by using NaBH4 (or H2SO4 in the case of addition to alkynes
Nitric acid is a strong acid. It will add NO2 to aromatic compounds (usually in the presence of another acid such as H2SO4) and will also oxidize primary alcohols and aldehydes to carboxylic acids.
Iodine is a good electrophile. It will react with carbon-carbon multiple bonds such as alkenes and alkynes, along with other nucleophiles. It is also used in the iodoform reaction
Potassium permanganate is a very strong oxidizing agent. It will oxidize primary alcohols (and aldehydes) to carboxylic acids, secondary alcohols to ketones, form diols from alkenes, and oxidatively cleave carbon-carbon multiple bonds.
Lithium di-isopropylamide (LDA) 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 Hofmann product in E2 reactions
Lithium aluminum hydride is a very strong reducing agent. It will reduce aldehydes, ketones, esters, and carboxylic acids to alcohols, and amides and nitriles to amines. It will also open epoxides
meta-chloroperoxybenzoic acid (m-CPBA) is an oxidizing agent. One of its main uses is in the formation of epoxides from alkenes. It will also oxidize ketones to form esters, a reaction known as the Baeyer-Villiger reaction
Sodium borohydride is a reagent for the reduction of ketones and aldehydes (it will also reduce acid halides). It is also used in the oxymercuration reaction to replace mercury with H.
Ozone will cleave alkenes and alkynes to give carbonyl compounds. This is called "oxidative cleavage." The products formed can be dependent on the type of workup used. Reductive workup preserves aldehydes, whereas oxidative workup will oxidize any aldehydes to carboxylic acids
Phosphorus tribromide is a reagent for converting alcohols to alkyl bromides. It will also convert carboxylic acids to acid bromides (acyl bromides).
Pyridinium chlorochomate (PCC) is a reagent for the oxidation of primary alcohols to aldehydes and secondary alcohols to ketones. It is much milder than reactants such as H2CrO4 and KMnO4, (which will oxidize primary alcohols to carboxylic acids).
Phosphorus trichloride is a reagent for the conversion of alcohols to alkyl chlorides. It will also convert carboxylic acids to acid chlorides (acyl chlorides),
Thionyl chloride is used for the formation of alkyl chlorides from alcohols, and acid chlorides (acyl chlorides) from carboxylic acids.
Tosyl chloride (TsCl) will convert alcohols to sulfonates, which are excellent leaving groups in elimination and substitution reactions.
Alkenes, alkynes, and alcohols dissolve
Positive test given by Alkenes and alkynes. Decolonizes the solution
Alkenes and alkynes turns solution brown
AgNO3 in alcohol
For alkyl and allylic halides. Forms a precipitate
Iodoform Test (I2/ OH)
Yellow solution if reacting with a methyl ketone or a methyl carbonyl
Test for aldehydes. Flask is coated with a mirror of silver
Chromate Oxidations or Jones Oxidation
Primary and secondary alcohols give a greenish solution
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