Transesterification [basic conditions]

Transesterification [basic conditions] Transesterification [basic conditions] Definition: Addition of alkoxide to an ester results in a new ester. Transesterification [basic conditions] Explained: Esters react with alcohols in a transformation called transesterification. This allows for the direct…

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Reduction to aldehydes [DIBAL-H]

Reduction to aldehydes [DIBAL-H] Reduction to aldehydes [DIBAL-H] Definition: Esters can be reduced to aldehydes with diisobutylaluminum hydride (DIBAL) a bulky source of hydride ion. Reduction to aldehydes [DIBAL] Explained: Although the aldehyde is intermediate…

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Reduction to alcohols [LiAlH4]

Reduction to alcohols [LiAlH4] Reduction to alcohols [LiAlH4] Definition: Addition of lithium aluminum hydride to esters leads to the formation of primary alcohols (after addition of acid). Reduction to alcohols [LiAlH4] Explained: When treated with lithium aluminum hydride abbreviated LAH,…

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Hydrolysis to carboxylic acid [basic]

Hydrolysis to carboxylic acid [basic] Hydrolysis to carboxylic acid [basic] Definition: Esters can be converted to carboxylic acids through treatment with strong base. Hydrolysis to carboxylic acids [basic] Explained: Esters can be hydrolyzed under acidic or basic conditions. These…

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Hydrolysis to carboxylic acid [acidic]

Hydrolysis to carboxylic acid [acidic] Hydrolysis to carboxylic acid [acidic] Definition: When an ester is treated with aqueous acid (and heat) it is converted into a carboxylic acid. Hydrolysis to carboxylic acids [acidic] Explained: Esters can be hydrolyzed…

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Ester formation [RCO2(–)]

Ester formation [RCO2(–)] Ester formation (RCO2‾) Definition: Alkyl halides (or tosylates) will react with carboxylate ion to form esters in SN2 reaction. Ester formation (RCO2‾) Explained: This is a one-step transformation. The nucleophile (acetate) attacks alkyl…

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Conversion to esters [ROH]

Conversion to esters [ROH] Conversion to esters [ROH] Definition: Acid chlorides are converted to esters when treated with alcohols. This reaction called alcoholysis. Conversion to esters [ROH] Explained: This reaction…

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Claisen condensation

Claisen condensation Claisen condensation Definition: When esters are treated with strong base, an enolate can be formed. By the attack of an ester enolate on a carbonyl group generates a…

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Esterification

Table of Contents Mechanism of Esterification Esterification is a chemical reaction that occurs between the acid (usually carboxylic acid) and the alcohol (or compounds containing the hydroxyl group) where esters…

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