[Woopy]

will E2 reactions compete with Sn2 for the reaction of methyl or ethyl tosylate with potassium phenoxide? Explain

I think because potassium phenoxide is a bulky base, it would do an E2 reaction, thus compete. Why would it even do sn2 though if it is bulky?

[discodermolide]

I do not think that potassium phenoxide is a bulky base.

[Woopy]

It's a ring structure, that doesn't count as bulky?

If so, does it compete?

[discodermolide]

Not in this case the ring is not a factor.
Can methyl tosylate undergo an E2 reaction? What about ethyl tosylate?

[PhDoc]

The most valuable learning to result from Organic Chemistry comes from proving (or disproving) something for yourself. Build a model of phenoxide, and assess whether you believe it is a bulky base when compared to tert-butoxide.

Now, let's talk about pKa. What's the pKa of ethanol? What's the pKa of phenol? What's the difference in basicity between the two alcohols in terms of orders of magnitude?

What is present in phenoxide that is not present in tert-butoxide? How does this help explain the lower pKa of phenol vs. ethanol?

Does it now make sense that phenoxide would be basic enough to effect an E2 reaction, or would it be more inclined to effect SN2?

Most importantly, what are the odds of getting an E2 with methyl tosylate? Ethyl tosylate?

[orgopete]

A general rule for elimination is primary much much less than secondary and less than tertiary halides or tosylates. Tertiary do not undergo SN2 reactions. Do you think it will be substitution or elimination?