April 20, 2024, 02:37:09 AM
Forum Rules: Read This Before Posting


Topic: Cynohydride and reduction  (Read 3522 times)

0 Members and 1 Guest are viewing this topic.

Offline physstudent1

  • Regular Member
  • ***
  • Posts: 82
  • Mole Snacks: +0/-0
Cynohydride and reduction
« on: March 12, 2009, 04:09:16 PM »


I thought A would lead to a NH double bonded at a C where the Br was also with a water molecular attached to this C that will tautomorize to a OH but this isn't correct?

Offline aldoxime_amine

  • Full Member
  • ****
  • Posts: 191
  • Mole Snacks: +7/-4
Re: Cynohydride and reduction
« Reply #1 on: March 12, 2009, 04:23:01 PM »
A is a carboxylic acid. (cyanide is an acid derivative)

Offline physstudent1

  • Regular Member
  • ***
  • Posts: 82
  • Mole Snacks: +0/-0
Re: Cynohydride and reduction
« Reply #2 on: March 12, 2009, 04:34:28 PM »
thankssss I must have erased that section in my book from my mind somehow...

Offline sjb

  • Global Moderator
  • Sr. Member
  • ***
  • Posts: 3652
  • Mole Snacks: +222/-42
  • Gender: Male
Re: Cynohydride and reduction
« Reply #3 on: March 13, 2009, 10:52:19 AM »
thankssss I must have erased that section in my book from my mind somehow...

A lot of it will depend on conditions, but basically cyanide is hydrolysed to amide (which is what I think you thought), but amide itself is usually hydrolysed faster to the acid. I'm not, however sure that LiAlD4 reduction (or indeed the unlabelled version) is that efficient with acids, as typically these cause the lithium salt to crash out of solution in a kinetic sink.

S

Sponsored Links