[hpl912]

this is the starting material:


when reacting with ethanol in acidic conditions (with HCl as catalyst), i suppose it only reacts (the ethoxy nucleophile group attaches) only on the ester side on the carbonyl, substituting the already present ethoxy group of the starting material and not the cyclohexanone ring? simply said, the product will virtually be the same as the starting material but with an OH on the carbonyl instead of O= ?

and if we replace ethanol with methanol in the same acidic condtions, then i suppose it will look the same as the starting material exept that the ethoxy group will be replaced by the methoxy nucleophile of the reagent?

or should the reagents react/attach to the alpha carbon of the cyclohexanone and the rest ester as leaving group?

[sjb]

What happens if the ethanol attacks the carbonyl of the ester? Not necessarily the hydrolysis that you've mentioned, but re-formation of the same compound?

So, the only useful way for the reaction to proceed is attack on the ketone. How do alcohols react with ketones?


If you had methanol, not ethanol, what happens when you attack the ester as before? And the ketone?

[hpl912]

if ethanol attacks carbonyl of ester with HCl catalyst:

it gives me same as the starting product  well.. exept the carbonyl now becomes alcohol

if ethanol attacks the ketone part with HCl catalyst:


and if i had methanol instead as the reagent, it will give the same product as the first and second except that it's -OCH3 that will be attached to the end instead of -OEt.

that's what i think... but i don't know which is correct. but i assume the first since the ester group seems to have lower pka than the cyclohexanone? so that the attack will be on this more reactive group in this compound

[hpl912]

anyoneee

[sjb]

In the first picture, you seem to missing a charge from bottom right to bottom left, and I think that OH is probably the better leaving group, to be honest. If you treat an ordinary ester, say ethyl acetate, with ethanol, I'm not sure any reaction really occurs (or if it does, the starting material is the same as the product). If you use methanol, you will get transesterification.

Have you learnt about acetal protection of ketones and aldehydes?

Your second scheme looks very unlikely - EtO₂CCH^- as a leaving group, and hydride shifts?

[Gerard]

if ethanol attacks carbonyl of ester with HCl catalyst:

it gives me same as the starting product  well.. exept the carbonyl now becomes alcohol

if ethanol attacks the ketone part with HCl catalyst:


and if i had methanol instead as the reagent, it will give the same product as the first and second except that it's -OCH3 that will be attached to the end instead of -OEt.

that's what i think... but i don't know which is correct. but i assume the first since the ester group seems to have lower pka than the cyclohexanone? so that the attack will be on this more reactive group in this compound

looks like a process of viral replication to me