Mechanisms Practice Questions

Mechanisms are the bread-and-butter of organic chemistry and practicing the mechanisms regularly is one of the best ways to ace your organic chemistry course!

Synthesis Practice Question 1: Robinson Annulation

In this post I wanna talk about one interesting synthesis question a student brought to me. So, without a further ado, here’s the question: Propose the reasonable synthetic sequence to accomplish the following transformation— While this synthesis may look intimidating, let’s break the whole process into small steps. This will help us see how we …

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Pinacol Rearrangement

Pinacol rearrangement is a specific elimination reaction that vicinal diols go through in acidic conditions. Unlike a typical E1 reaction that gives you an alkene, the pinacol rearrangement gives you an aldehyde or a ketone instead. Here’s the general scheme for the reaction: As you can see, the pinacol rearrangement also causes the carbon backbone …

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How to Convert a Trans Alkene into a Cis Alkene?

Suppose you need to accomplish the following transformation: This is not the most trivial of questions as there are no single-step reactions that can realistically accomplish this transformation. Of course, there are some isomerization techniques out there, but they all favor the more thermodynamically stable molecule. And since the more thermodynamically stable double bond is …

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