Oxidation

[akimhaneul]

There is a question in organic odyssey that asks which molecule is most easily oxidized.

A) 2-pentanone
B) pentanal
C) 2-hydroxy 3- methyl pentane
D) ethyl propyl ether
E) 2-hydroxybutyl ethyl ether

Why is the answer b? I thought c is a more reduced form so it can be oxidized more?



It's question 42 in chapter 13.

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[akimhaneul]

Bump


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[akimhaneul]

Bump


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[Azide047]

This one is tough. My guess is the aldehyde in choice B has the most electrophilic alpha carbon and thus an OH- nucleophile could attack it and replace the H in a multi step workup. Aldehydes easily oxidize to carboxylic acids.

Primary alcohols oxidize to aldehydes which oxidize to carboxylic acids.

Secondary alcohols (choice C) oxidize to ketones.

The difference here is probably due to spontaneity of the reaction.
C is a close one though.


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