Synthesis (6) – Reactions of Alcohols

by James

in Alcohols, Synthesis, Uncategorized

The Alcohol Reaction Map

Having now finished (at long last) covering the key reactions of alcohols, let’s stop to put everything in perspective.

Over the past 18 posts, we covered reactions such as:

  • Ether formation via substitution reactions
  • Elimination of alcohols to form alkenes
  • Conversion of alcohols to alkyl halides via substitution reactions
  • Cleavage of ethers
  • Opening of epoxides
  • Reactions of thiols

In my experience, there’s nothing that helps doing this like making a “map” of reactions. So let’s put each of these reactions onto a single page, in “reaction map” format:

mini alcohol rxn map

It’s not easy to do this without making some tradeoffs. Here, you’ll note that “alcohols” are all bunched up into a single box, which includes primary, secondary, and tertiary alcohols. As we’ve stated before, not all reactions work on all types of alcohols (for instance, we can’t oxidize tertiary alcohols).

Using this map requires some judgement. While it would have been possible to separate the categories, that would have ended up making the map a lot more visually distracting. So in order to use this properly, it’s up to you to understand which reactions work for each type of alcohol [which is covered in the initial blog posts on each topic, as well as in the notes on the reaction map below].

Similarly, all the “carbonyls” (aldehydes, ketones, carboxylic acids, esters) have been grouped together, for now. When we cover future sections we’ll expand them out, but at this stage I wanted to keep things as simple as possible.

A Really Big Reaction Map

You might recall that my previous post on synthesis covered reactions of alkanes, alkyl halides, alkenes, and alkynes. Let’s now take the same “map” and add alcohols. Things are starting to get crowded – I count 69 different reactions!

This map covers most of the reactions you’ll see for alcohols, alkenes, alkynes, alkanes, and alkyl halides. One thing it doesn’t cover is formation of the various conjugate bases and acids from each species.

Here is the map in downloadable PDF format

Here’s the big map.

alcohol rxn map

I welcome comments and suggestions – and would even pay for someone who has design skills to make this look better!

In the next series on MOC, we’ll cover reactions of organometallics. Hopefully this won’t take nearly a year like this series on alcohols has!

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Yash Goyal

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