Organic Chemistry 2

Demystifying Alcohol Oxidations

May 21, 2015

Today’s post in a nutshell: The Familiar Key Step At The Heart Of (Almost) All Alcohol Oxidation Reactions When I was learning organic chemistry I remember the reagents for oxidation reactions completely coming out of left field. KMnO4, K2Cr2O7, PCC, CrO3, Swern, Dess—Martin ? Hold on. Where did these reagents come from? How do they […]

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Elimination of Alcohols To Alkenes With POCl3

April 28, 2015

Here’s what we talk about today: more eliminations of alcohols!  Note that this reagent isn’t covered in all courses, but I’ll include it here for completeness’ sake. We’ve talked about 2 ways to convert alcohols to alkenes so far: Option #1: Convert the alcohol to an alkyl halide [with SOCl2, PBr3, or a hydrohalic acid] and then […]

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Elimination Reactions of Alcohols

April 16, 2015

Here’s a summary of what we talk about in today’s post. Hydrohalic acids (HX)  plus alcohols give substitution products… We just saw that treating an alcohol with a strong hydrohalic acid – think HCl, HBr, or HI – resulted in the formation of alkyl halides. With a tertiary alcohol like the one drawn below, this […]

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PBr3 and SOCl2

March 20, 2015

Lately we’ve been talking a lot about converting alcohols to good leaving groups [halides] [tosylates and mesylates] You might think we’d be done already, but not yet! In today’s post we talk about a third important method for converting alcohols to good leaving groups – by using the reagents phosphorus tribromide (PBr3) and thionyl chloride […]

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Tosylates And Mesylates

March 10, 2015

Today we’re going to talk about a different way of making alcohols into good leaving groups – by turning them into tosylates and mesylates (“organosulfonates”). Here’s a brief summary of what we’ll cover here: Making Alcohols Into Good Leaving Groups, Part 2 We’ve seen that alcohols are poor substrates for substitution reactions. The main problem is that […]

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The Organic Chemistry Behind “The Pill”

February 13, 2015

The Most Interesting Man In The World passed away the other week. No, not THAT guy. He’s just an actor. The OTHER guy. The OTHER guy is Carl Djerassi, organic chemist, professor, author, playwright, and most notably, “Father of the Pill”. Lots of people these days – especially startups –  talk about changing the world. […]

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The Williamson Ether Synthesis

October 24, 2014

In the last post, we discussed the acid-base properties of alcohols. Two posts ago, we said that acid-base reactions are often used to “set up” substitution and elimination reactions of alcohols.  In this post, we’ll talk about what is probably the best example of this last point –  the Williamson Ether Synthesis. The Williamson Ether […]

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How To Make Alcohols More Reactive

How To Make Alcohols More Reactive

October 6, 2014

In the last post we explored some of the properties and nomenclature of alcohols. We said that alcohols tend to have high boiling points due to hydrogen bonding, and that  we commonly divide alcohols into the categories  “primary”, “secondary”,  and “tertiary” (with a nod to the unique, “methanol”) according to how many carbons are attached to the C […]

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Alcohols (1) – Nomenclature and Properties

September 17, 2014

In this next series of posts we are going to discuss the reactions of alcohols. As a functional group, alcohols are introduced fairly early in organic chemistry. Their reactions, however, are usually not covered until near the end of Org 1 – at least after subjects like substitution and elimination reactions have been explored. That’s […]

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How Concepts Build Up In Org 2

September 9, 2014

OK. Having looked at the Org 1 Concept Map, let’s ask the next logical question: what does a typical Org 2 course look like? One general observation: the way functional groups are covered in your typical two-semester organic chemistry course generally follows the oxidation ladder. Look at the progression:  alkanes (low oxidation state) first, then […]

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