Organic Chemistry 1

Thiols And Thioethers

Thiols And Thioethers

July 5, 2015

Here’s a summary of today’s post on thiols: Thiols and Thioethers One of the most powerful insights from learning the periodic table is the fact elements in the same period (column) have similar chemical properties. For instance Alkali metals (Li, Na, K…) all shed an electron relatively easily to form monovalent cations Halogens (F, Cl, Br) […]

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Protecting Groups For Alcohols

Protecting Groups For Alcohols

June 17, 2015

Summary for today’s post on Protecting Groups: When Alcohols Get In the Way As we’ve seen in previous posts in this series, alcohols are very versatile functional groups that participate in a variety of reactions. They can be deprotonated with base (making them good nucleophiles in substitution reactions), protonated (making them good leaving groups in […]

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Intramolecular Reactions of Alcohols and Ethers

Intramolecular Reactions of Alcohols and Ethers

June 12, 2015

“Intramolecular Reactions Make Me Crumple Into The Fetal Position Crying For My Mommy” Here’s a topic which doesnt really fit neatly in with what we’ve discussed before but it’s essential to any discussion of alcohols and ethers. Intramolecular reactions.  Here’s the executive summary: Intramolecular reactions [i.e. reactions where two functional groups in a molecule react […]

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PBr3 and SOCl2

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

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

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

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

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

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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