[kcchan128]

Hi there,

I did an experiment on hydrolysis of tert-butyl chloride. Basically there were 2 types of solvents (water and acetone) used. We were just playing with these parameters by changing the volume of these 2 solvents.

There's one part of the experiment where only acetone were used.

From what I know, tert-butyl chloride would be forming a tertiary carbocation, this must be a SN1 reaction.
Also, for SN1 reaction, polar protic solvent is preferred as the hydrogen bonding can stabilize the +ve chage on carbocation, lowering the energy of the transition state.

Based on all the listed condition, how can acetone react with t-butyl chloride to form HCl as a product?
Am i on the right track trying to figure out the mechanism (pushing arrow) of this reaction? (acetone and t-butyl chloride)

I'm not sure how the mechanism going to be like.


thanks.

[Smrt guy]

Acetone is probably not reacting at all.  Chances are the mechanism would be E1.

[xiaojunzhang]

In the experiment,maybe the hydrolysis didn't run at all.Moreover,the acetone is very stable in your reaction.

[cananian]

1) first of all   why you didnt try water  alone to do  hydrolysis  ( no need for other solvent, when the system is under
2) acetone to react as a nucleophile needs to get the enol or enolate  forms which requires an acidic or basic media(which is not available).eventhough, if that is formed, it is very week either   nucleophile  to act through (SN1) or very week base to act through ( E1) COMPARED WITH WATER which is more nucleophile than acetone


 

[cananian]

1) first of all   why you didnt try water  alone to do  hydrolysis  ( no need for other solvent, when the system is under reflux

2) acetone to react as a nucleophile needs to get the enol or enolate  forms which requires an acidic or basic media(which is not available).eventhough, if that is formed, it is very week either   nucleophile  to act through (SN1) or very week base to act through ( E1) COMPARED WITH WATER which is more nucleophile than acetone