[jorbarrientos]

hey everyone, im having a hard time trying to figure out the products from the following reaction:

You have benzyl chloride and treat it with Cl2 at 145°C. I know this is going to form Ph-CH-Cl2.

Then it says that you treat the previous product with NaOH 5% in acetone and water, and this is where im stuck, since i dont understand what type of reaction would happen there, i mean, i think -OH would act as a nucleophile and attack the CH-Cl2 Carbon via SN2, but that would give Ph-CH(OH)Cl as a product and i dont know if this is right, so i need you to please tell me what happens when you have a good nucleophile but it is going to attack a Carbon with 2 Cl´s attached to it. Is my prediction correct? Is it attacked twice and that produces a Diol?... i would also appreciate if you could explain a little bit about the solvent used in this reaction, since i dont really understand the low NaOH concentration and that acetone-water mixture they chose.

[Schrödinger]

Well... The initial product need not necessarily be a dichloro product. It would actually be a mixture of di and trichlorinated products. And if the Cl2 used is in excess, you could even end up getting a BHC derivative.

Assuming that it is not in excess, the OH would most certainly act as a nuclephile, and substitute according as the product is di (diol = aldehyde) or tri (triol = acid). Or atleast that's what I believe would happen. Please correct me if I'm wrong

Solvent : The acetone component of the solvent is probably used for the organic compound at hand, the benzyl chloride.

[discodermolide]

I think you will end up with benzaldehyde.
This process is an oxidation. Treatment of the dichloro compound (Ph-CH-Cl2 where the C atom is at the aldehyde oxidation level) with dilute OH- will produce Ph-CH-(OH)(Cl) which is a chlorinated hemiacetal. If it reacts further you will obtain the hemiacetal, which is just hydrated benzaldehyde.

[Schrödinger]

Yes, but what about the possibility of tri chlorination? I mean, what happens when the final product is a trichlorinated one? Is it possible at all?

[discodermolide]

Yes, but what about the possibility of tri chlorination? I mean, what happens when the final product is a trichlorinated one? Is it possible at all?

Trichlorination is possible, however, it would be a minor side product, owing to the steric contstraints.