December 22, 2024, 03:30:38 PM
Forum Rules: Read This Before Posting


« previous next »
Pages: [1]   Go Down

Topic: Reactivity with hydroxide ion  (Read 3301 times)

0 Members and 3 Guests are viewing this topic.

Offline LHM

  • Full Member
  • ****
  • Posts: 144
  • Mole Snacks: +1/-3
Reactivity with hydroxide ion
« on: January 08, 2011, 08:48:23 PM »
Why is (CH3)3CBr more likely to react with OH- than (CH3)3CCl? I think it has to do with electronegativity, but isn't Cl more electronegative so it's more likely to take the electrons from the C atom it's attached to and create a partial positive charge over that C?
Logged

Offline Schrödinger

  • Chemist
  • Sr. Member
  • *
  • Posts: 1162
  • Mole Snacks: +138/-98
  • Gender: Male
Re: Reactivity with hydroxide ion
« Reply #1 on: January 09, 2011, 12:15:05 AM »
This is a substitution reaction, and the intermediate formed is a carbocation.
http://en.wikipedia.org/wiki/SN1_reaction

Br is a better leaving group than Cl, and since formation of the carbocation is the Rate Determining Step, (CH3)3CBr is more likely to react with OH- than (CH3)3CCl.
Logged
"Destiny is not a matter of chance; but a matter of choice. It is not a thing to be waited for; it is a thing to be achieved."
- William Jennings Bryan

Offline LHM

  • Full Member
  • ****
  • Posts: 144
  • Mole Snacks: +1/-3
Re: Reactivity with hydroxide ion
« Reply #2 on: January 09, 2011, 11:11:49 AM »
But what makes Br a better leaving group than Cl?
Logged

Offline Schrödinger

  • Chemist
  • Sr. Member
  • *
  • Posts: 1162
  • Mole Snacks: +138/-98
  • Gender: Male
Re: Reactivity with hydroxide ion
« Reply #3 on: January 10, 2011, 10:47:37 AM »
C-Br bond is weaker than the C-Cl bond
Logged
"Destiny is not a matter of chance; but a matter of choice. It is not a thing to be waited for; it is a thing to be achieved."
- William Jennings Bryan
Pages: [1]   Go Up
« previous next »
Sponsored Links