Reactions
Reactants Reagents Products Help
CCOC(=O)C(Cc1ccccc1)C(=O)OCC Magnify O=S(O)(O)=O.O
(hot, dilute)
c1ccc(cc1)CCC(=O)O Magnify

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.
C(=O)=O Magnify


CCOC(=O)C(Cc1ccccc1)C(=O)C Magnify O=S(O)(O)=O.O
(hot, dilute)
CC(=O)CCc1ccccc1 Magnify

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.
C(=O)=O Magnify


CCOC(=O)C1(CCCC1)C(=O)OCC Magnify O=S(O)(O)=O.O
(hot, dilute)
C1CCC(C1)C(=O)O Magnify

Note: Hot acid to yield decarboxylation results in a carboxylic acid substituent on a closed ring.
C(=O)=O Magnify


c1ccc(cc1)S(=O)(=O)O Magnify O=S(O)(O)=O.O
(hot, dilute)
c1ccccc1 Magnify

Note: Sulfonation of benzene is reversible with hot (steaming), dilute acid. This can make it useful as a temporary 'blocking group.'


CC(C)(CCCCO[Si](C)(C)C)O Magnify O=S(O)(O)=O.O
(hot, dilute)
CC(C)(CCCCO)O Magnify

Note: Aqueous acid may also be used to deprotect silyl ethers


CC(C)(CCCC1OCCO1)O Magnify O=S(O)(O)=O.O
(hot, dilute)
C(CO)O Magnify

Note: Acetal protecting groups may subsequently be removed by aqueous acid hydrolysis
CC(C)(CCCC=O)O Magnify


CC1(OCCO1)CCC(c2ccccc2)(c3ccccc3)O Magnify O=S(O)(O)=O.O
(hot, dilute)
C(CO)O Magnify

Note: Acetal protecting groups may subsequently be removed by aqueous acid hydrolysis after the highly reactive organometallic step has been completed
CC(=O)CCC(c1ccccc1)(c2ccccc2)O Magnify


C[C@H](C#N)O Magnify O=S(O)(O)=O.O
(hot, dilute)
C[C@H](C(=O)O)O Magnify

Note: Acid-catalyzed hydrolysis of nitriles to carboxylic acids
N Magnify


COC1(CCCC1)OC Magnify O=S(O)(O)=O.O
(hot, dilute)
C1CCC(=O)C1 Magnify

Note: Acid-catalyzed hydrolysis of an acetal back to the component carbonyl and alcohols. Excess H2O is assumed to drive the reaction equilibrium.
CO Magnify CO Magnify


CC1(OCCO1)C Magnify O=S(O)(O)=O.O
(hot, dilute)
C(CO)O Magnify

Note: Acid-catalyzed hydrolysis of a cyclic acetal back to component molecules
CC(=O)C Magnify


CCN=C1CCCCC1 Magnify O=S(O)(O)=O.O
(hot, dilute)
C1CCC(=O)CC1 Magnify

Note: Acid-catalyzed hydrolysis of an imine back to component molecules.
CCN Magnify


CC(=C)N1CCCCC1 Magnify O=S(O)(O)=O.O
(hot, dilute)
C1CCNCC1 Magnify

Note: Acid-catalyzed hydrolysis of an enamine back to component molecules.
CC(=O)C Magnify


CC(=O)OC(=O)C Magnify O=S(O)(O)=O.O
(hot, dilute)
CC(=O)O Magnify

Note: Carboxylic acids can be prepared from more reactive derivatives like anhydrides by hydrolysis, in this case helped by acid catalysis.
CC(=O)O Magnify


CCOC(=O)C Magnify O=S(O)(O)=O.O
(hot, dilute)
CC(=O)O Magnify

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.
CCO Magnify


CC(=O)N Magnify O=S(O)(O)=O.O
(hot, dilute)
CC(=O)O Magnify

Note: Amides are among the least reactive carboxylic acid derivatives. One of the few reactions that can be completed is acid-catalyzed hydrolysis
N Magnify


CC#N Magnify O=S(O)(O)=O.O
(hot, dilute)
CC(=O)O Magnify

Note: Nitriles are counted among carboxylic acid derivatives in part because they can be hydrolyzed under acid conditions to yield carboxylic acids.
N Magnify


CCN1C(=O)c2ccccc2C1=O Magnify O=S(O)(O)=O.O
(hot, dilute)
CCN Magnify

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.
c1ccc(c(c1)C(=O)O)C(=O)O Magnify


c1ccc(cc1)[N+]#N.OS(=O)(=O)[O-] Magnify O=S(O)(O)=O.O
(hot, dilute)
c1ccc(cc1)O Magnify

Note: Treating arenediazonium salts with aqueous acid results in substitution by water. This provides one of the only synthetic methods to produce phenols.


CCOC(=O)C(C)(C(=O)OCC)NC(=O)C Magnify O=S(O)(O)=O.O
(hot, dilute)
C[C@@H](C(=O)O)N Magnify

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.
C[C@H](C(=O)O)N Magnify


C[C@H](C#N)N Magnify O=S(O)(O)=O.O
(hot, dilute)
C[C@H](C(=O)O)N Magnify

Note: Hydrolysis of the nitrile yields the carboxylic acid of the amino acid.


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