Organic Chemistry 1

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

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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Maybe they should call them, “Formal Wins” ?

Maybe they should call them, “Formal Wins” ?

August 15, 2014

In April of this year, Braves reliever Luis Avilan came in with a 5-1 lead in the 8th inning. Eight batters later, he’d given up five runs, blowing the lead. Thankfully for him, the Braves came back in the top of the 9th and reliever David Carpenter nailed down the save. The result: Avilan got [...]

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Bridged Bicyclic Rings (And How To Name Them)

August 14, 2014

In the last post we started our discussion of structures with more than one ring, using decalin as our key example. We saw how much the stereochemistry at the ring junction can affect the overall shape of the molecule, as well as its stability. What we didn’t talk about is that the ring junction of decalin [...]

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Fused Rings

August 5, 2014

At the beginning of this series I said that the fact that carbon can form rings leads to all kinds of interesting consequences. We’re going to see many examples of that in our post today! So far, we’ve only talked about cyclic molecules containing one ring. But, of course, molecules with multiple rings are very common [...]

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Which Cyclohexane Chair Is Of Lower Energy?

July 23, 2014

In the last post, we introduced A values and said they were a useful tool for determining which groups are “bulkiest” on a cyclohexane ring. The greater the A-value (bulk), the more favoured the equatorial conformer will be (versus axial). We saw that hydroxyl groups (OH) have a relatively low A-value (0.87), methyl groups are [...]

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Substituted Cyclohexanes: “A Values”

July 1, 2014

In the last post we saw that adding a methyl group to cyclohexane results in two chair conformers that are unequal in energy. We saw that the conformer where the methyl group was equatorial is the most stable, since it avoids destabilizing diaxial interactions (technically, gauche interactions) that are present in the conformer when the methyl group is axial. We also said [...]

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