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.

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

Sorry, here it is.

Here it is.

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

 

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?

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

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

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