Lecture Questions 49 & 50

Viewing 1 post (of 1 total)
  • Author
  • #29810
    Elliott Drake

    For ?49, I was torn between B & C, but the answer is A. The explanation is that each ketone oxygen went from six bonds, to four (becoming hydroxy groups), and that this is reduction. But when I look at the reaction, I just see the bond changing from double to the carbonyl carbon, into two single bonds (one with H and one with C). Please help me see the reduction, as both oxygens maintain their two lone pairs.

    For ?50, I guessed D, because the conjugate base would be most stable. I understand the explanation that A is more acidic because less electrons donated to the oxygen d/t it being a primary hydroxy group. Does this factor simply have greater effect than the higher stability of tertiary and ring conjugate base stability?

    Appreciate any and all help.

Viewing 1 post (of 1 total)
  • You must be logged in to reply to this topic.