CHEM 343: REDOX REACTIONS CHAPTER 20
8 Cards in this Set
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Aldehyde/Ketone + Raney Nickel --->
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Corresponding alcohol 1o for aldehydes 2o for ketones
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Aldo-Keto containing compound + NaBH4
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Keto-alcohol containing compound Aldehyde more reactive against sodium borohydride
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Aldo-Keto containing compound + NaBH4/CeCl3 in H2O/EtOH -->
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Aldo-alcohol containing compound Selectively targets ketone through temporary aldehyde protection
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1o alcohol + PCC in DCM -->
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Aldehyde Non acidic conditions prevent side reactions
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Aldehyde + mCPBA -->
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Ester product Which group becomes part of the ester depends on migration speed: H>3oalkyl>2oalkyl=phenyl>1oalkyl>methyl
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Aldehyde + mCPBA -->
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Carboxylic acid
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Alkene + mCPBA -->
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Epoxide This reaction is chemoselective: more nucleophilic alkenes react first Stereochemistry is retained, and it can create a racemic product
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1o alcohol + H2CrO4 -->
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Aldehyde initially, but continually oxidation produces a carboxylic acid end product
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CHEM 343: REDOX REACTIONS CHAPTER 20