Can sn1 and e2 occur on primary with this situation?

[virtualmaster999]

Hi all!

So I came across this situation before, and I think I remember hearing or seeing that this could work, but I wanna confirm it. So I know that sn1/e1 don't usually occur on primary (because it would push e2/sn2 to occur). but what if you had a weak base/weak nucleophile, such as methanol? Wouldn't that have to force e1/sn1 because of it being weak?

Thanks in advance!

---

Members don't see this ad.

 

[FeralisExtremum]

No, the carbocation formation would still be too unstable. The only way you'd see SN1/E1 on a primary carbon would be if it was allylic or benzylic.

 

[virtualmaster999]

No, the carbocation formation would still be too unstable. The only way you'd see SN1/E1 on a primary carbon would be if it was allylic or benzylic.

That makes sense, thanks!

 

[DAT Destroyer]

Hi all!

So I came across this situation before, and I think I remember hearing or seeing that this could work, but I wanna confirm it. So I know that sn1/e1 don't usually occur on primary (because it would push e2/sn2 to occur). but what if you had a weak base/weak nucleophile, such as methanol? Wouldn't that have to force e1/sn1 because of it being weak?

Thanks in advance!

Consider a primary halide reacting with water or alcohol.....NO REACTION occurs,,,,,This is a commonly asked trick problem. Sn1 or E1 ? Not a chance,,,,,,the carbocation cannot form.

Hope this helps.

Dr. Romano

 

[virtualmaster999]

Consider a primary halide reacting with water or alcohol.....NO REACTION occurs,,,,,This is a commonly asked trick problem. Sn1 or E1 ? Not a chance,,,,,,the carbocation cannot form.

Hope this helps.

Dr. Romano

Oh I see! So if a question involves a weak base/nucleophile like water or R-OH, the answer is always NO REACTION?

 

[DAT Destroyer]

Oh I see! So if a question involves a weak base/nucleophile like water or R-OH, the answer is always NO REACTION?

Yes,,,,that is true, primary halides do not react......

 

[virtualmaster999]

Yes,,,,that is true, primary halides do not react......

Thanks so much! I always appreciate the help!

 

[DAT Destroyer]

Thanks so much! I always appreciate the help!

Always glad to help! Keep up the great work!