October 18, 2021, 01:12:16 PM
Forum Rules: Read This Before Posting


Topic: What is the product of Diazotisation of propan - 1 - amine  (Read 2551 times)

0 Members and 1 Guest are viewing this topic.

Offline shubhamrawal

  • Regular Member
  • ***
  • Posts: 13
  • Mole Snacks: +0/-0
What is the product of Diazotisation of propan - 1 - amine
« on: June 23, 2015, 03:17:26 PM »
Is it Propan - 1 - ol or Propan - 2 - ol ?

Offline kriggy

  • Chemist
  • Sr. Member
  • *
  • Posts: 1472
  • Mole Snacks: +128/-16
Re: What is the product of Diazotisation of propan - 1 - amine
« Reply #1 on: June 23, 2015, 05:45:21 PM »
What do you think? If the diazogroup is on carbon number one, could you get substitution on carbon number two?
Also, what are the conditions? Because you can get chloride too (if you use excess of HCl)

Offline pgk

  • Chemist
  • Full Member
  • *
  • Posts: 892
  • Mole Snacks: +97/-24
Re: What is the product of Diazotisation of propan - 1 - amine
« Reply #2 on: June 24, 2015, 10:05:58 AM »
The major product of diazotisation of propan - 1 – amine, is propan - 2 – ol, accompanied by a small amount of propan - 1 – ol, together with propene.
The reaction mechanism starts by thermal liberation of gaseous nitrogen and formation of the corresponding carbocation:
CH3CH2CH2-N(+)ΞΝ, Cl(-)  →  CH3CH2CH2(+) + N2↑ + Cl(-)
Try to explain the formation of all above products from propane-1-carbocation and why propan - 2 – ol is the major product.
Reference: Peter Sykes, A Guidebook to Mechanism in Organic Chemistry, 2nd Edition, Longmans LTD, London, (1965), p. 85
« Last Edit: June 24, 2015, 01:20:06 PM by pgk »

Offline shubhamrawal

  • Regular Member
  • ***
  • Posts: 13
  • Mole Snacks: +0/-0
Re: What is the product of Diazotisation of propan - 1 - amine
« Reply #3 on: June 25, 2015, 07:56:05 AM »
Hi PGK ,
Thanks for replying to my question .
I also think that that propane-2-ol should be formed by hydrid shift in carbo cation rearrangement because carbo cation rearrangement is also observed in digitization of 1-cyclopentyl methan-1-amine .

But the answer suggested by this link is Propan-1-ol - http://chemwiki.ucdavis.edu/Organic_Chemistry/Amines/Reactions_of_Amines/The_Reaction_of_Amines_with_Nitrous_Acid

Offline sjb

  • Global Moderator
  • Sr. Member
  • ***
  • Posts: 3585
  • Mole Snacks: +219/-42
  • Gender: Male
Re: What is the product of Diazotisation of propan - 1 - amine
« Reply #4 on: June 25, 2015, 09:30:56 AM »
Hi PGK ,
Thanks for replying to my question .
I also think that that propane-2-ol should be formed by hydrid shift in carbo cation rearrangement because carbo cation rearrangement is also observed in digitization of 1-cyclopentyl methan-1-amine .

But the answer suggested by this link is Propan-1-ol - http://chemwiki.ucdavis.edu/Organic_Chemistry/Amines/Reactions_of_Amines/The_Reaction_of_Amines_with_Nitrous_Acid

Note the caveat below the equation on that page.
Quote
...The propan-1-ol will be only one product among many - including propan-2-ol, propene, 1-chloropropane, 2-chloropropane and others...

I think what the page is saying is that for each molecule of amine, you get a molecule of dinitrogen, and (presumably) depending on exact conditions you may get varying amounts of each of the potential organic products. I doubt whether this is of as preparative use as per ArNH2 diazotation

Offline pgk

  • Chemist
  • Full Member
  • *
  • Posts: 892
  • Mole Snacks: +97/-24
Re: What is the product of Diazotisation of propan - 1 - amine
« Reply #5 on: June 25, 2015, 10:37:03 AM »
Reference: Peter Sykes, A Guidebook to Mechanism in Organic Chemistry, 2nd Edition, Longmans LTD, London, (1965), p. 85

Offline shubhamrawal

  • Regular Member
  • ***
  • Posts: 13
  • Mole Snacks: +0/-0
Re: What is the product of Diazotisation of propan - 1 - amine
« Reply #6 on: June 25, 2015, 04:07:18 PM »
Thanks PGK

Sponsored Links