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(hot, dilute)
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Note: Acid hydrolysis of esters to carboxylic acids. More importantly, once you produce and heat a carboxylic acid that is beta to another carbonyl (such as an ester), decarboxylation (loss of CO2) will readily occur via a 6-membered cyclic transition state. The net result of malonic ester synthesis is the apparent alkylation of acetic acid.
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(hot, dilute)
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Note: Acid hydrolysis of the ester to a carboxylic acid which is beta to the ketone. Under heated conditions, this will readily decarboxylate to yield a net result that is the apparent alkylation of acetone.
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(hot, dilute)
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Note: Hot acid to yield decarboxylation results in a carboxylic acid substituent on a closed ring.
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(hot, dilute)
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Note: Sulfonation of benzene is reversible with hot (steaming), dilute acid. This can make it useful as a temporary 'blocking group.'
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(hot, dilute)
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Note: Aqueous acid may also be used to deprotect silyl ethers
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(hot, dilute)
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Note: Acetal protecting groups may subsequently be removed by aqueous acid hydrolysis
|
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(hot, dilute)
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Note: Acetal protecting groups may subsequently be removed by aqueous acid hydrolysis after the highly reactive organometallic step has been completed
|
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(hot, dilute)
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Note: Acid-catalyzed hydrolysis of nitriles to carboxylic acids
|
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(hot, dilute)
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Note: Acid-catalyzed hydrolysis of an acetal back to the component carbonyl and alcohols. Excess H2O is assumed to drive the reaction equilibrium.
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(hot, dilute)
|
Note: Acid-catalyzed hydrolysis of a cyclic acetal back to component molecules
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(hot, dilute)
|
Note: Acid-catalyzed hydrolysis of an imine back to component molecules.
|
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(hot, dilute)
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Note: Acid-catalyzed hydrolysis of an enamine back to component molecules.
|
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(hot, dilute)
|
Note: Carboxylic acids can be prepared from more reactive derivatives like anhydrides by hydrolysis, in this case helped by acid catalysis.
|
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(hot, dilute)
|
Note: Acid-catalyzed hydrolysis of an ester to a carboxylic acid, with excess water assumed to drive the reaction equilibrium. Virtually all carboxylic acid derivatives can be hydrolyzed to carboxylic acids with aqueous acid.
|
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(hot, dilute)
|
Note: Amides are among the least reactive carboxylic acid derivatives. One of the few reactions that can be completed is acid-catalyzed hydrolysis
|
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(hot, dilute)
|
Note: Nitriles are counted among carboxylic acid derivatives in part because they can be hydrolyzed under acid conditions to yield carboxylic acids.
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(hot, dilute)
|
Note: The final step of Gabriel synthesis of a primary amine is hydrolysis of the phthalimide. This is comparable to hydrolysis of an amide to an amine and carboxylic acid.
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(hot, dilute)
|
Note: Treating arenediazonium salts with aqueous acid results in substitution by water. This provides one of the only synthetic methods to produce phenols.
|
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(hot, dilute)
|
Note: Amino-malonate derived synthesis of amino acids concludes with acid hydrolysis of the amide and esters, including decarboxylation of the resulting beta-di-carboxylic acid.
|
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(hot, dilute)
|
Note: Hydrolysis of the nitrile yields the carboxylic acid of the amino acid.
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(0.066 sec)
Link
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