Orgo question

[299678]

Advertisement - Members don't see this ad

Which proton is most acidic in 2 hexanone?
a) c1
b) c3
c) C4
d) C5
e) C6

Obviously correct answer should be C1 or C3, I don't know which one
Please explain me in details to support your answer. Thank yu

 

[darkwalk]

I would say C1 because C3 is attached to more electron donating carbons.

 

[JBarr29]

Carbon 1 would be more acidic - it is easier to pull off terminal hydrogens then internal ones.

 

[Maygyver]

I would say C3 because the enolate would be more stable as resonance. Not sure though. Do you have the answer key?

 

[sfoksn]

I would have to say C1 because of C1 because: 1. it is terminal H, 2. because it would form resonance. It is also less electron rich so I would think C1 would liek to gain the negative charge more.

 

[Maygyver]

OP....the answer is....?

 

[299678]

C1, thanks guys