April 27, 2024, 07:24:12 PM
Forum Rules: Read This Before Posting


Topic: Relative Basicity  (Read 2867 times)

0 Members and 1 Guest are viewing this topic.

Offline Ben Cohen

  • Regular Member
  • ***
  • Posts: 35
  • Mole Snacks: +2/-2
Relative Basicity
« on: January 02, 2013, 03:02:00 AM »
The addition of 0.01 mol of which of the following to
100 mL of H2O will give the most alkaline aqueous
solution?
(A) NH3
(B) HONH2
(C) CH3NH2
(D) H2NNH2

I drew the four molecules and was between B and D, but I chose D because it had 2 lone pairs on the Nitrogens, and lone pairs tend to give more basicity. However, the answer was C. I have no idea regarding the reasoning behind this.
I also tried to think about conjugate acid stability.
NH4+ is, I thought, relatively stable. The conjugate acids of B and D don't seem too stable (especially D, because with one of the nitrogens having 3 H's and the other having 2, it doesn't seem good, and also there would be resonance).

Additionally, I considered formal charge, but every atom in all 4 of the compounds has a formal charge of 0.

I'm pretty confused, and I would really like to hear the rationale behind this.

Thanks in advance.
« Last Edit: January 02, 2013, 03:39:23 AM by Ben Cohen »

Offline Hunter2

  • Sr. Member
  • *****
  • Posts: 2180
  • Mole Snacks: +167/-48
  • Gender: Male
  • Vena Lausa moris pax drux bis totis
Re: Relative Basicity
« Reply #1 on: January 02, 2013, 03:36:55 AM »
C because of positiv inductive effect of Methyl group.

http://www.chemguide.co.uk/basicorg/acidbase/bases.html

Offline Ben Cohen

  • Regular Member
  • ***
  • Posts: 35
  • Mole Snacks: +2/-2
Re: Relative Basicity
« Reply #2 on: January 02, 2013, 03:50:28 AM »
C because of positiv inductive effect of Methyl group.

http://www.chemguide.co.uk/basicorg/acidbase/bases.html

Thank you so much this explained it so well!

Sponsored Links