TBR Organic Book 1 Chp. 3 Phase 3 # 29

[athockey7]

The answer choice says that HOC6H5 is a stronger conjugate acid than HSCH3...

i do not understand this because i thought S makes for a better acid than O because it is bigger and can stabilize better after H leaves

if someone could explain would be appreciated!

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[oxelhs]

The benzene ring offers more stability in this case than the larger size of the S offers.

 

[FeinMS]

The benzene ring offers more stability in this case than the larger size of the S offers.

Via delocalization of electron due to resonance in conjugate base.

 

[athockey7]

ahh thanks guys

didnt even realize that was a benzene