[Soarer]

Hi everyone,

In this Organic Chemistry II practice question, 4-methylphenol is reacted, in three steps, to form 2-propenyl-4-methylphenol. The first and third steps are provided; the question asks what the second step is.

The first (provided) step is treatment with NaOH. I understand that this turns the -OH into a negatively charged -O^- group, right?

The second step, according to the answer, is treatment with BrCH₂CHCH₂, or 3-bromopropene. The third (provided) step is simply heat.

I cannot find this type of reaction in my book. Could someone please explain the details/mechanism of this type of reaction?

(I don't have the option of asking a professor, since I am preparing to retake this class, but the session hasn't started yet. I am determined to perform better this time around!)

Thanks everyone!
- Soarer

[Doc Oc]

This is a named reaction (starts with a C).

[Soarer]

There are a lot of reactions that begin with C - any more information?

[Doc Oc]

Yes.  The reaction is actually named after someone (ie; Grignard, Kiliani-Fisher, etc).  Their name starts with a C.  The information you're looking for is probably buried in the section in your book dealing with electrophilic/nucleophilic aromatic substitutions.  And this reaction is a rearrangement.

[zaphraud]

Just ask yourself where the most reactive protons are, and you have your answer.

You should also be able to predict the possible formation of a side product(s) as reactants are depleted and products accumulate, especially if they are in the wrong proportions.

[OnePiece]

[3,3]-sigmatopic rearrangement. that's one heck of a clue already.

[Soarer]

Figured it out - it's a CLAISEN rearrangement! 

Sure enough, I had skipped right over it several times.

Thanks everyone!