Organic Chemistry 1

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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Making Alkyl Halides From Alcohols

February 27, 2015

Making Alkyl Halides From Alcohols In today’s post we show that treating alcohols with HCl, HBr, or HI (which all fall under the catch-all term “HX” where X is a halide) results in the formation of alkyl halides. We’ve said many times in this series of posts that alcohols are poor substrates for SN1 and SN2 […]

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Ether Synthesis Via Alcohols And Acid

November 14, 2014

Last post I got a little ahead of myself. I was all excited about getting into the reactions of ethers, and forgot that there’s one last method for ether synthesis that we haven’t covered. It’s actually not that general so you can likely skip ahead. But for the sake of completeness, here it is. Remember when we said […]

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Williamson Ether Synthesis: Planning

October 30, 2014

In the last post we introduced the Williamson ether synthesis,  one of the most straightforward ways we know of to make an ether. If you’ve been in the trenches long enough, you would have also noticed that it’s actually nothing that new –  the Williamson is just “rebranding” of a reaction we’ve seen before,  the SN2 […]

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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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Organic Chemistry IUPAC Nomenclature Demystified With A Simple Puzzle Piece Approach

Organic Chemistry IUPAC Nomenclature Demystified With A Simple Puzzle Piece Approach

October 21, 2014

IUPAC Nomenclature Demystified with a Simple Puzzle-Piece Approach, by Leah Fisch Note from James: This is a guest post by Leah Fisch of Leah4Sci.com , an online resource for learning organic chemistry, MCAT preparation, and other science topics . This is an epic, comprehensive post on  organic chemistry IUPAC nomenclature. You might want to bookmark this page for […]

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Alcohols (3) – Acidity and Basicity

October 17, 2014

In the last post we said that one of the keys to the reactions of alcohols as we go forward is that the conjugate acid is a better leaving group and the conjugate base is a better nucleophile. We might have gotten a little ahead of ourselves broaching that topic, because we haven’t yet really revisited some […]

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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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How Concepts Build Up In Org 1 (“The Pyramid”)

September 5, 2014

I LOVE making maps. Whenever I played adventure games as a kid (or, let’s face it, as an adult) I often made meticulous maps of how each area led to the next. Any time I really want to understand something, I have to write everything out and make a map to connect things together – usually […]

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