April 19, 2024, 12:04:36 AM
Forum Rules: Read This Before Posting


Topic: Penicillin G Hydrolysis  (Read 7476 times)

0 Members and 1 Guest are viewing this topic.

Offline AhmedEzatAlzawalaty

  • Full Member
  • ****
  • Posts: 191
  • Mole Snacks: +4/-31
  • Gender: Male
Penicillin G Hydrolysis
« on: September 26, 2007, 07:11:58 PM »
I want to know how benzylpenicillin(Penicillin G) gets hydrolysed in acid medium and how the ring opening occurs.
I know that substitution with EWG on alpha position of acyl carbon increases stability to acid-catalyzed hydrolysis because nucleophilicity of amide side chain carbonyl decreases so it would not be attacked by acid but i dont get how hydrolysis occurs exactly step by step till ring opening happens.
Thank you.

Offline AWK

  • Retired Staff
  • Sr. Member
  • *
  • Posts: 7979
  • Mole Snacks: +555/-93
  • Gender: Male
Re: Penicillin G Hydrolysis
« Reply #1 on: September 27, 2007, 01:00:23 AM »
You can find mechanism of acidic hydrolysis of amides in any university organic chemistry textbooks and on internet
AWK

Offline AhmedEzatAlzawalaty

  • Full Member
  • ****
  • Posts: 191
  • Mole Snacks: +4/-31
  • Gender: Male
Re: Penicillin G Hydrolysis
« Reply #2 on: September 29, 2007, 12:01:50 PM »
but what is the effect of substitution at alpha acyl carbon on hydrolysis?and what is the role of acetamide in hydrolysis too?

Sponsored Links