April 25, 2024, 03:23:17 PM
Forum Rules: Read This Before Posting


« previous next »
Pages: [1]   Go Down

Topic: C8H8O2 to C8H6O2Br2  (Read 2664 times)

0 Members and 1 Guest are viewing this topic.

Offline owlpower

  • Regular Member
  • ***
  • Posts: 43
  • Mole Snacks: +0/-1
C8H8O2 to C8H6O2Br2
« on: July 13, 2016, 06:51:07 AM »
When 4,methylbenzoic acid reacts with Br2(aq), why doesn't C8H8O2Br2 form? I thought the positions of CH3 (2,4 directing) and COOH (1,3 directing) will support Bromination.

Logged

Offline sjb

  • Global Moderator
  • Sr. Member
  • ***
  • Posts: 3652
  • Mole Snacks: +222/-42
  • Gender: Male
Re: C8H8O2 to C8H6O2Br2
« Reply #1 on: July 13, 2016, 07:49:35 AM »
Quote from: owlpower on July 13, 2016, 06:51:07 AM
When 4-methylbenzoic acid reacts with Br2(aq), why doesn't C8H8O2Br2 form? I thought the positions of CH3 (2,4 directing) and COOH (1,3 directing) will support Bromination.

Other reactions may compete. Are either methyl or carboxylic acid strong activators?
Logged

Offline owlpower

  • Regular Member
  • ***
  • Posts: 43
  • Mole Snacks: +0/-1
Re: C8H8O2 to C8H6O2Br2
« Reply #2 on: July 13, 2016, 08:43:20 AM »
CH3 is an activator (electron donating) and COOH is not (electron withdrawing). Thus they will support bromination due to their relative positions, correct?

What other reactions could possibly occur? I can only think of free radical sub for CH3.
Logged

Offline AWK

  • Retired Staff
  • Sr. Member
  • *
  • Posts: 7979
  • Mole Snacks: +555/-93
  • Gender: Male
Re: C8H8O2 to C8H6O2Br2
« Reply #3 on: July 13, 2016, 01:54:20 PM »
Logged
AWK

Offline Enthalpy

  • Chemist
  • Sr. Member
  • *
  • Posts: 4041
  • Mole Snacks: +304/-59
Re: C8H8O2 to C8H6O2Br2
« Reply #4 on: July 17, 2016, 02:44:00 PM »
The first message doesn't mention any catalyst. Does bromine react at the aromatic ring then ? Or rather at the methyl? Thanks!
Logged
Pages: [1]   Go Up
« previous next »
Sponsored Links