Glucose Reaction

[Sciencegeeknm]

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.

[hypervalent_iodine]

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

[Sciencegeeknm]

Sorry, here it is.

Here it is.

[hypervalent_iodine]

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

[Sciencegeeknm]

 

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?

[hypervalent_iodine]

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

[Sciencegeeknm]

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

[hypervalent_iodine]

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