January 10, 2025, 02:50:05 PM
Forum Rules: Read This Before Posting


« previous next »
Pages: [1]   Go Down

Topic: Elimination-Addition: Benzyne  (Read 2186 times)

0 Members and 1 Guest are viewing this topic.

Offline davidenarb

  • Full Member
  • ****
  • Posts: 133
  • Mole Snacks: +0/-1
Elimination-Addition: Benzyne
« on: August 04, 2014, 07:05:16 PM »
Hi all,

Bellow, we have an Elimination-Addition reaction.

Will we have two products if the conditions were : 1) NaOH, 350°C 2) H3O+ ? or it works only if the base is NaNH2 ?
Logged

Offline rwiew

  • Regular Member
  • ***
  • Posts: 88
  • Mole Snacks: +10/-6
  • Gender: Male
  • MChem, PhD Researcher in Chemical Biology
Re: Elimination-Addition: Benzyne
« Reply #1 on: August 04, 2014, 08:03:58 PM »
NaOH won't be strong enough a base to form the benzyne. You could get an SNAr mechanism with a nucleophile like OH-, but you don't have an electron withdrawing group on the ring to facilitate that.
Logged

Offline zsinger

  • Full Member
  • ****
  • Posts: 374
  • Mole Snacks: +18/-60
  • Gender: Male
  • Graduate Chemist
Re: Elimination-Addition: Benzyne
« Reply #2 on: August 04, 2014, 09:02:27 PM »
Amide usually works better, and the above is correct.  One needs a strong deactivator like nitro groups to facilitate SnAr.
          -Z
Logged
"The answer is of zero significance if one cannot distinctly arrive at said place with an explanation"

Offline orgopete

  • Chemist
  • Sr. Member
  • *
  • Posts: 2636
  • Mole Snacks: +213/-71
    • Curved Arrow Press
Re: Elimination-Addition: Benzyne
« Reply #3 on: August 05, 2014, 01:07:43 AM »
Quote from: davidenarb on August 04, 2014, 07:05:16 PM
Will we have two products if the conditions were : 1) NaOH, 350°C 2) H3O+ ? or it works only if the base is NaNH2 ?

Is this a literature procedure? If it is, then I think you will get a mixture.
Logged
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.
Pages: [1]   Go Up
« previous next »
Sponsored Links