Reactions
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CCOC(=O)C Magnify
CC(=O)[O-].[Na+] Magnify

Warning: When working with esters and bases, be sure the base matches the ester, otherwise you may end up with unintended trans-esterification results.
CC[O-].[Na+] Magnify


CC(=O)Cl Magnify
CC(=O)[O-].[Na+] Magnify

Note: Carboxylic acids can be prepared from more reactive derivatives like acid chlorides by hydrolysis, in this case under basic conditions. Note that the base will deprotonate the resulting carboxylic acid following the primary reaction.


CCOC(=O)C Magnify
CC(=O)[O-].[Na+] Magnify

Note: Saponification of an ester, driven by base. The exchange of water vs. the ester alcohol should be a reversible equilibrium, but subsequent deprotonation of the resulting carboxylic acid makes this an irreversible reaction.
CC[O-].[Na+] Magnify


CC(=O)N Magnify
CC(=N)[O-].[Na+] Magnify

Warning: Base driven hydrolysis of amides will not work when acid-base reactions can occur first. Even for tertiary amides, hydrolysis is an unlikely result.


CC(=O)C Magnify CI Magnify
CO Magnify

Warning: Direct enolate alkylation driven by base will not be very effective as simple Sn2 substitution of the base / nucleophile against the alkyl halide is more likely to result.


CC(=O)CC(=O)C Magnify CI Magnify
CC(C(=O)C)C(=O)C Magnify

Note: Direct enolate alkylation of a double active methylene group is more likely as deprotonation will readily occur.


c1ccc2c(c1)C(=O)NC2=O Magnify
c1ccc2c(c1)C(=NC2=O)[O-].[Na+] Magnify

Note: Gabriel synthesis of primary amines starts with deprotonation of phthalimide to produce a good nucleophile.


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

Note: The cyanohydrin breaks down under basic conditions to yield an aldose, one carbon shorter than before the Wohl degradation.


CC(C)(C)Br Magnify
CC(=C)C Magnify

Note: E2 - Hydroxide ion is a strong base


CCBr Magnify
CCO Magnify

Note: Sn2 - Hydroxide ion is a strong nucleophile


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