A Brief Introduction to Organic Chemistry – FINAL EXAM

This is an example from a recent publication (Org. Lett. 2011, Article ASAP. DOI: 10.1021/ol201354k).

Scheme 1

In short, if you mix 2-hydroxy-2-methylbutan-3-one (1) with sodium hydride in the presence or absence (sic!) of ethyl formate (2) and then perform an acid workup, you will get compound 3.

1. What is the structure of compound 3? Mind the stereochemistry.

2. What is the mechanism for the formation of compound 3?

3. What is the correct IUPAC name for compound 3?

Good luck!

 

One Response to Org Chem 101

  1. notmedchem says:

    So I spent 45 minutes working through them mechanisms. Wow..Aldol reactions galore. Not I believe in the furanyl oxonium acting as a nucleophile, but it’s the only thing that works. Dean-Stark Paradise.

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