I studied that when alcohol is treated with isocyanate and then undergone hydrolysis (or methanolosis), carbamate is formed. But when we use carbamate as trichloroacetyl isocyanate, why hydrolysis doesn't give amine containing trichloroacetyl group rather than the one containing ester group?

enter image description here

http://reag.paperplane.io/00002775.htm#5 In any material, there is no explanation about it, and I'm really curious.


The triple chlorine substitution substantially increases the electrophilicity of the carbonyl group, making is more susceptible to nucleophilic addition. Given that this step is probably endothermic, we expect the transition state to be late and having significant build up of negative charge. The inductive effects from the substitution will stabilize the transition state and increase the rate of addition and hence, the overall rate of hydrolysis of carbonyl group over the other.

| improve this answer | |

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Not the answer you're looking for? Browse other questions tagged or ask your own question.