Depto. Química Orgánica

ADDITION OF HYDROGEN, HYDRIDES AND BORANE TO ALDEHYDES AND KETONES
(REDUCTION)

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15/07/2017
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Reduction of aldehydes and ketones
The addition of hydrogen, hydrides or borane to the C=O group of aldehydes or ketones leads to an alcohol and therefore this is an excellent way to preparing the latter.
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CATALYTIC HYDROGENATION
The reaction is very similar to that studied for the alkenes.
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 IMPORTANT:
Be careful if there are alkene or alkyne functions in the molecule because they'll get reduced.
Other functions might be reduced too!!!
Peruse the table.
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Always be aware of possible competition between the existing functions when attempting a complex synthesis scheme.
Don't forget that the C=O group of aldehydes and ketones can be "protected" against undesired side-reactions.
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HYDRIDE ADDITION
This reaction was already introduced in the chapter about alcohols as a method for their preparation.
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BORANE ADDITION
The reaction is very similar to that studied for the alkenes.
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In the case of aldehydes and ketones, the boron atom always ends up bonded to oxygen.
IMPORTANT: Again, DO FOCUS on the possible competition of other functions to boranes.
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Please, notice that if you carefully compare the three tables on this page, the reactivity of the different functional groups is quite different.
It is an art your getting around with a chemoselective reduction, i.e. affecting only the function(s) we do choose.
DON'T YOU FRET!!! This is an art that is learned with time, practice and patience.
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