[Urbanium]

In this "allylmethylsulfonium", which of these four sites can be (in theory) most easily deprotonated or is most susceptible to loosing a proton upon action of some base?

[sjb]

In this "allylmethylsulfonium", which of these four sites can be (in theory) most easily deprotonated or is most susceptible to loosing a proton upon action of some base?

What factors do you think may affect this?

[Urbanium]

What factors do you think may affect this?

A) positive charge on sulfur
B) sp2 electrons i.e. the allylic double bond

But unsure in which way..

[Babcock_Hall]

Don't both a and b indicate the same carbon?

[clarkstill]

What about resonance/pi conjugation?

[Babcock_Hall]

clarkstill,

Thank you; I misread or misinterpreted what the OP wrote in b).

@OP Can resonance delocalization stabilize a negative charge?

[orgopete]

A) positive charge on sulfur
B) sp2 electrons i.e. the allylic double bond

But unsure in which way..

If you compared propane with acetone in a halo form reaction, what effect do you think the carbonyl group and the addition of a halogen have on the acidity of the methyl hydrogens?

[shafaifer]

I would stick to d, thread starter.

[orgopete]

I would stick to d, thread starter.

The second most acidic.