[david123]

I am not sure how to even start,

is it an addition rxn, i know the reagent is polar protic meaning Sn1 but where is the alkylhalide. so confused.

[Babcock_Hall]

I would start by asking what sort of substance KOH is.  Another thing I might do is to draw out the structure of the sulfur-containing compound.

[david123]

Thanks for your reply. I drew out the Dimethyl sulfate and understood that KOH is strong nucleophile, but what is the mechanism approach i take from there, how do i know where it is going to be attacked.

Does the OH bond get removed, or do we move the pie bond to KOH to form a carbocation which then causes the dimethylsulfate to bond with the main branch?

Thanks so much

[Babcock_Hall]

KOH is also a strong base.  Are there any protons it could remove?

[discodermolide]

That compound is the enol form of 2-phenyl acetaldehyde!


And dimethyl sulfate is a reagent for methylation.
So I'm not sure where phenol fits into this question.

[Babcock_Hall]

Discodermolide,

You raise a good point that I missed entirely; it would seem that either the drawing is incorrect, or the wording of the problem is incorrect.  I am tempted to suggest assuming that the starting material is simply phenol.

[discodermolide]

Discodermolide,

You raise a good point that I missed entirely; it would seem that either the drawing is incorrect, or the wording of the problem is incorrect.  I am tempted to suggest assuming that the starting material is simply phenol.

I would agree that the SM is probably phenol.

[Babcock_Hall]

@OP,

Given the pK_a values of phenol (about 10) and water (about 15), what will be the equilibrium of an acid-base reaction between them?