Organic Chemistry

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How do you name the products?

2-ethyl-1,3-hexanediol is oxidized. One option is that the primary alcohol is oxidized, but not the secondary. Another option, the secondary is oxidized but not the primary. Last option is that they are both oxidized. How do you name these products?

  • Organic Chemistry -

    If primary alcohol is oxidized once, you get an aldehyde group (if oxidized twice you would get a carboxylic acid)

    2-ethyl-3-hydroxyhexanal

    If secondary alcohol is oxidized, you get a ketone:

    1-hydroxy-2-ethylhexan-3-one

    If both oxidize, you have a ketone with an aldehyde substituent:

    1-formyl-2-ethylhexan-3-one

  • Organic Chemistry -

    I'm not up on the newest organic nomenclature but I would use these names. I have found that there is no ABSOLUTELY correct way; i.e., many names are correct. I would advise getting a second opinion.
    #1.
    2-ethyl-3-hydroxy-1-hexanal

    #2.
    2-ethyl-1-hydroxy-3-hexanone (or hexan-3-one).

    #3.
    2-ethylhexane-1-al-3-one

  • Organic Chemistry -

    1-hexanal is redundant. In an aldehyde, the aldehyde carbon is always #1.

    After seeing DrBob's answer, I'd change the substituent orders in my answer to be alphabetic:

    2-ethyl-3-hydroxyhexanal
    2-ethyl-1-hydroxyhexan-3-one
    2-ethyl-1-formylhexan-3-one

  • Organic Chemistry -

    I know you're right about the 1 being redundant; however, I stick it in anyway. It isn't absolutely correct but it isn't absolutely incorrect either (at least in my mind). :-).

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