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11 Cards in this Set

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  • Back
Aldehydes and ketones react with water to yield ?
1,1 diols or geminal (gem) diols.
The hydration rxn is reversible, and a gem diol can ...
eliminate water to regenerate an aldehyde or ketone
The exact position of the equilibrium btwn a gem diol and an aldehyde or ketone depends on ...
the structure of the carbonyl compound
The equilibrium in nucleophilic addition of hydration genrally favors the _____ _______ for steric reasons, ____ ____ ___ is favored for a few simple aldehydes
- carbonyl compound

- the gem diol
The nucleophilic addition of water to an aldehyde or ketone is ______ in pure water but is catalyzed ....
- slow

- by both acid and base.
Like all catalysts, acids and bases don't change the _____ _____ _____ ____ ; they affect only the .....
- position of the equilibrium

- rate at which the hydration rxn occurs
The acid-catalyzed hydration rxn begins with ....

then...
a protonation of the carbonyl oxygen atom, which places a positive charge on the oxygen and makes the carbonyl group more electrophilic

Subsequent nucleophilic addition of water to the protonated gem diol, which loses H+ to give the neutral product
What is the key difference btwn the base-catalyzed and acid catalyzed rxns?
Base-catalyzed rxn takes place rapidly because water is converted into hydroxide ion, a much better nucleophile

The acid catalyzed rxn takes place rapidly because the carbonyl compound is converted by protonation into a much better electrophile
Base-catalyzed rxn takes place rapidly because ?
water is converted into hydroxide ion, a much better nucleophile
The acid catalyzed rxn takes place rapidly because ?
the carbonyl compound is converted by protonation into a much better electrophile
Treatment of an aldehyde or ketone with CH3OH, H2O, HCL, HBR, or H2SO4 does not normally lead to
an isolable addition product