September 29, 2024, 03:25:51 AM
Forum Rules: Read This Before Posting


Topic: question about hydration/dehydration reaction  (Read 4550 times)

0 Members and 2 Guests are viewing this topic.

Offline Pringles

  • New Member
  • **
  • Posts: 3
  • Mole Snacks: +0/-0
question about hydration/dehydration reaction
« on: December 13, 2009, 07:43:55 PM »
Is the Product of this reaction: 1-hexene + water CH3-CH2-CH2-CH2-CH(doublebond)CH2 + H2O
equal to this?: 1-hexanol CH3-CH2-CH2-CH2-CH2-OH

if this is the answer then the reverse (dehydration) would be:

1-hexanol CH3-CH2-CH2-CH2-CH2-CH2-OH  --> 2-hexene + water CH3-CH2-CH2-CH2-CH-CH3 *the OH is bonded to the 2nd carbon


Can anyone explain this please?

Offline Pringles

  • New Member
  • **
  • Posts: 3
  • Mole Snacks: +0/-0
Re: question about hydration/dehydration reaction
« Reply #1 on: December 13, 2009, 08:09:17 PM »
the question  is basically: how do u get 1-hexanol from an alkene + water

because this doesn't seem to follow markovnikov's rule

Offline orgopete

  • Chemist
  • Sr. Member
  • *
  • Posts: 2636
  • Mole Snacks: +213/-71
    • Curved Arrow Press
Re: question about hydration/dehydration reaction
« Reply #2 on: December 13, 2009, 09:39:13 PM »
Check the hydroboration/oxidation procedure.
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Offline fadouge

  • Very New Member
  • *
  • Posts: 1
  • Mole Snacks: +0/-0
Re: question about hydration/dehydration reaction
« Reply #3 on: December 13, 2009, 10:58:29 PM »
I think this is due to rearragement to more stable intermediate.

Offline bromidewind

  • Full Member
  • ****
  • Posts: 106
  • Mole Snacks: +10/-7
Re: question about hydration/dehydration reaction
« Reply #4 on: December 16, 2009, 09:07:46 PM »
Anti-Markovnikov addition of alcohols to an alkene follows the hydroboration mechanism.

Alkene + BH3-THF, followed by H2O2 and NaOH -> anti-Markovnikov alcohol

Sponsored Links