Orgo Q: Nucleophilic Substitution Rxn vs. Addition-Elimination Rxn

[ap594]

---

Members don't see this ad.

I just needed some quick clarification as to what the difference is here, if there is any. I have been going through the EK1001 Orgo book and they describe the rxn of acetyl chloride with water as a nucleophilic substitution because the water is a nucleophile and is replacing the Cl, which is then the leaving group. But, I just did the TPR 4 Diagnostic and it said that a similar reaction was an addition-elimination reaction and not a nucleophilic substitution reaction (because I chose the latter and got it incorrect). Any clarification would be great. Thanks guys.

 

[PiBond]

I just needed some quick clarification as to what the difference is here, if there is any. I have been going through the EK1001 Orgo book and they describe the rxn of acetyl chloride with water as a nucleophilic substitution because the water is a nucleophile and is replacing the Cl, which is then the leaving group. But, I just did the TPR 4 Diagnostic and it said that a similar reaction was an addition-elimination reaction and not a nucleophilic substitution reaction (because I chose the latter and got it incorrect). Any clarification would be great. Thanks guys.

i would probably challenge EK orgo. in addition elimination (for example in carbonyl chemistry) you'll first add a new group and create a tetrahedral intermediate. Then if the leaving group is good/decent a pi-bond will reform and eliminate the leaving group. in nucleophilic substitution (ie Sn2) we are not "eliminating" in the same sense. if the answer choice had said nucleophilic acyl substitution that would have been correct.

 

[ap594]

thank you, sir! that helps a lot.