April 27, 2024, 02:01:51 PM
Forum Rules: Read This Before Posting


Topic: Detailed Mechanism  (Read 6463 times)

0 Members and 1 Guest are viewing this topic.

Offline lrisNil

  • Regular Member
  • ***
  • Posts: 37
  • Mole Snacks: +0/-1
  • Gender: Female
  • Fan of Francis Crick
Re: Detailed Mechanism
« Reply #15 on: March 07, 2015, 07:47:42 PM »
Add the electrons on the nitrogen as well as the hydrogen?
But the nitrogen I drew above has 4 bonds and no lone pairs I believe  (assuming I did it correct thus far)

It does have 2 H's though but what do you mean by "add?   :

Iris Lin

Offline lrisNil

  • Regular Member
  • ***
  • Posts: 37
  • Mole Snacks: +0/-1
  • Gender: Female
  • Fan of Francis Crick
Re: Detailed Mechanism
« Reply #16 on: March 07, 2015, 08:03:23 PM »
Oh.. Is the N positively charged after it performed a nucleophilic attack?
And there is a C=O nearby , O with lone pairs.
Can those electrons attack the N, even though the N has 4 bonds?

Is this correct?
Iris Lin

Offline orgopete

  • Chemist
  • Sr. Member
  • *
  • Posts: 2636
  • Mole Snacks: +213/-71
    • Curved Arrow Press
Re: Detailed Mechanism
« Reply #17 on: March 08, 2015, 12:37:58 AM »
Well now, we're getting to the nitty gritty of this. The amine will be more basic than the just formed amide. There will be a proton transfer. You probably need two equivalents of the amine as one will become tied up as the HCl salt, but I digress. The nitrogen will have one hydrogen and one lone pair. Now, whether you use the lone pair to add or you write the addition as acid catalyzed, you'll have to decide.
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Offline lrisNil

  • Regular Member
  • ***
  • Posts: 37
  • Mole Snacks: +0/-1
  • Gender: Female
  • Fan of Francis Crick
Re: Detailed Mechanism
« Reply #18 on: March 08, 2015, 05:51:38 PM »
Thank you Dr. Pete!

Is the arrow in the diagram that I most recently posted the proton transfer?
Or do I just write "proton transfer" and take the H away from the N and put it on the C=O above?

(my sheet says you can just write proton transfer, so now I think I don't even need the arrow I drew)
Iris Lin

Offline lrisNil

  • Regular Member
  • ***
  • Posts: 37
  • Mole Snacks: +0/-1
  • Gender: Female
  • Fan of Francis Crick
Re: Detailed Mechanism
« Reply #19 on: March 08, 2015, 06:20:19 PM »
I attempted the proton transfer, does this look correct? >.<
Iris Lin

Offline lrisNil

  • Regular Member
  • ***
  • Posts: 37
  • Mole Snacks: +0/-1
  • Gender: Female
  • Fan of Francis Crick
Re: Detailed Mechanism
« Reply #20 on: March 08, 2015, 06:35:40 PM »
Then I did this, and I think it leads to the product
i wonder if this is correct, or are there any mistakes ?  :-\
Iris Lin

Sponsored Links