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11 Cards in this Set
- Front
- Back
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Aldehydes and ketones react with water to yield ?
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1,1 diols or geminal (gem) diols.
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The hydration rxn is reversible, and a gem diol can ...
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eliminate water to regenerate an aldehyde or ketone
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The exact position of the equilibrium btwn a gem diol and an aldehyde or ketone depends on ...
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the structure of the carbonyl compound
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The equilibrium in nucleophilic addition of hydration genrally favors the _____ _______ for steric reasons, ____ ____ ___ is favored for a few simple aldehydes
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- carbonyl compound
- the gem diol |
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The nucleophilic addition of water to an aldehyde or ketone is ______ in pure water but is catalyzed ....
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- slow
- by both acid and base. |
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Like all catalysts, acids and bases don't change the _____ _____ _____ ____ ; they affect only the .....
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- position of the equilibrium
- rate at which the hydration rxn occurs |
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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 |
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What is the key difference btwn the base-catalyzed and acid catalyzed rxns?
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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 |
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Base-catalyzed rxn takes place rapidly because ?
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water is converted into hydroxide ion, a much better nucleophile
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The acid catalyzed rxn takes place rapidly because ?
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the carbonyl compound is converted by protonation into a much better electrophile
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Treatment of an aldehyde or ketone with CH3OH, H2O, HCL, HBR, or H2SO4 does not normally lead to
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an isolable addition product
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