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Reduction using NaBH4
Sodium borohydride (NaBH4) is a weak reducing agent and therefore only reacts with aldehydes and ketones. A reduction reaction leads to less bonds to an oxygen atoms and more bonds to hydrogen atoms.
- Reduction of an aldehyde gives a primary alcohol.
- Reduction of a ketone gives a secondary alcohol.
Wize Concept
Reduction reactions are just attack with a hydride (H-) nucleophile!
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Reduction using LiAlH4
Lithium aluminum hydride (LiAlH4) is a strong reducing agent and therefore only reacts with all carbonyls. A reduction reaction leads to less bonds to an oxgyen atoms and more bonds to hydrogen atoms.
- Reduction of an aldehyde gives a primary alcohol.
- Reduction of a ketone gives a secondary alcohol.
- Reduction of esters and acids gives a primary alcohol.
- Reduction of amides gives amines.
Wize Concept
Since LiAlH4 is so much more reactive than NaBH4, the reaction is done at low temperatures and in non-protic solvents (Et2O).
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Example: Reduction Reactions
Fill in the blanks for the following reduction reactions. In some cases, multiple reaction steps may be necessary.
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Example: Reduction Reactions
Predict the product(s) of the following reduction reaction. Is the product optically active?
