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PCC as an oxidizing agent
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Amna_5729
#1 Posted : Tuesday, July 21, 2020 1:15:58 AM
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Can PCC oxidize secondary alcohols to ketones?

Is there a similar reducing agent that only reduces aldehydes back to primary alcohols?
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INSTR_Katerina_102
#2 Posted : Tuesday, July 21, 2020 1:23:55 AM
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Hi Anna,

Yeah, PCC can oxidize 2ndary alcohols --> ketones.

Sodium borohydride will reduce aldehydes --> alcohols but not carboxylic acids.

Sodium borohydride will also reduce ketones --> alcohols though.

Usually in practice we try to get at the aldehyde by taking advantage of its lack of steric hinderance, but without priming from the passage the idea of selecting for a an aldehyde vs a ketone is something that is more advanced than the scope of the MCAT.

I hope this helps!

Katt
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