August 15, 2020, 11:06:07 AM
Forum Rules: Read This Before Posting

Topic: Can someone check if my mechanisms are correct?  (Read 585 times)

0 Members and 1 Guest are viewing this topic.

Offline yourdeath01

  • Regular Member
  • ***
  • Posts: 33
  • Mole Snacks: +1/-1
Can someone check if my mechanisms are correct?
« on: December 04, 2019, 07:28:47 PM »
All 3 reactions:

For part a: Basically Thiamine hydrochloride (vitamin B1) in presence of NaOH it losses 2 protons to become nucleophilic and adds (with a proton) to carbonyl of benzaldehyde.
Then: thiamine residue is electron withdrawing which increase acidity of adjacent hydrogen atom, which makes it so that the base can attack the hydrogen to yield a carbanion, which attacks the carbonyl of another benzaldehyde molecule. Loss of thiamine residue from product produces benzoin

Here is my mechanism for part a:

page 1:

page 2:

Is my mechanism in terms of arrow pushing and everything else all good?!


For part b: Benzoin is then converted to benzil through the use of NH4NO3 (ammonium nitrate) through the use of copper (II) acetate catalyst which will oxidize the benzoin

Here is my mechanism for part b:

Alternative method:

Mechanism all good? Is the alternative better to use here or stay on the one above it?


For part C: The benzil is treated with KOH which will make it go through molecular rearrangement discovered by von Liebig How the rearrangement happens? KOH makes Nu attack on 1 of the C= O and then it makes its phenyl group move to other carbonyl. This yields initially potassium benzilate but this dissolves after the mixture is heated

Mechanism for part C:

Again, is this mechanism all good?

I am probably overthinking this lol, but I don't want to lose out points on silly mistakes, so let me know if I should make adjustment to any of the 3 parts/mechanisms I posted above.

Offline AWK

  • Retired Staff
  • Sr. Member
  • *
  • Posts: 7457
  • Mole Snacks: +523/-87
  • Gender: Male
Re: Can someone check if my mechanisms are correct?
« Reply #1 on: December 05, 2019, 02:16:56 AM »
Reaction of copper(I) oxidation is unbalanced.
Google - Copper-Catalyzed Oxidation of Benzoin to Benzil


Sponsored Links