Jump to content


Photo
- - - - -

Glucose Reaction


  • Please log in to reply
7 replies to this topic

#1 Sciencegeeknm

Sciencegeeknm

    Quark

  • Members
  • 15 posts
  • LocationLeicester, England

Posted 8 December 2016 - 06:34 PM

Hi,

The following reaction(see photo attached) was talked about on a lecture I watched on YouTube.
There was no mechanism mentioned so I tried to work it out myself.
Can you confirm if I'm on the right track?

Firstly the Na H (in excess) would de protonate all of the OH groups on the glucose molecule.

Then the now O- groups would react by SN2 pathway on the benzyl chloride molecules. Now all the former O- groups would be joined to benzyl CH2 units?

Thanks.

Nick.
  • 0

#2 hypervalent_iodine

hypervalent_iodine

    Malevolent Viper

  • Moderators
  • 3,419 posts

Posted 9 December 2016 - 09:39 AM

Your picture hasn't attached. Could you try again?
  • 0

#3 Sciencegeeknm

Sciencegeeknm

    Quark

  • Members
  • 15 posts
  • LocationLeicester, England

Posted 9 December 2016 - 05:59 PM

Sorry, here it is.
Here it is.

Attached Thumbnails

  • image.jpeg

  • 0

#4 hypervalent_iodine

hypervalent_iodine

    Malevolent Viper

  • Moderators
  • 3,419 posts

Posted 9 December 2016 - 08:04 PM

Okay, then I would agree with your mechanism except that it would be SN1, not 2.
  • 0

#5 Sciencegeeknm

Sciencegeeknm

    Quark

  • Members
  • 15 posts
  • LocationLeicester, England

Posted 10 December 2016 - 07:57 AM


Interesting that you say SN1 as the teacher says this would go by SN2 alkylation.

If it went by SN1 then you get a primary carbocation?
  • 0

#6 hypervalent_iodine

hypervalent_iodine

    Malevolent Viper

  • Moderators
  • 3,419 posts

Posted 10 December 2016 - 08:56 AM

Yes, but it's benzylic. They happen to be quite stable due to the aromatic ring.
  • 0

#7 Sciencegeeknm

Sciencegeeknm

    Quark

  • Members
  • 15 posts
  • LocationLeicester, England

Posted 10 December 2016 - 11:35 AM

Ah ok. Stabilisation through resonance. So would it ever be SN2?
  • 0

#8 hypervalent_iodine

hypervalent_iodine

    Malevolent Viper

  • Moderators
  • 3,419 posts

Posted 10 December 2016 - 07:33 PM

I believe so, it's just more often SN1.
  • 0




0 user(s) are reading this topic

0 members, 0 guests, 0 anonymous users