Alcohols

Grignard Reactions And Synthesis (2)

Grignard Reactions And Synthesis (2)

January 19, 2016

Here’s the summary for today’s post on synthesis incorporating Grignard reagents and oxidants: Synthesis Using Grignard Reagents (Part 2) In the last post we saw how to approach some fairly straightforward synthesis problems using Grignard reagents. We learned how to think backwards from our final products (alcohols) to appropriate precursors for a Grignard reaction (aldehydes, […]

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Synthesis Using Grignard Reagents (1)

Synthesis Using Grignard Reagents (1)

January 13, 2016

Here’s the bottom line for today’s post on solving synthesis problems involving Grignard reagents. Solving Synthesis Problems Involving Grignard Reagents Now that we’ve covered some of the most important reactions of Grignard reagents, it’s time to actually apply this knowledge to practical matters. And by practical matters, I mean synthesis. After all, the point of learning […]

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Synthesis (6) – Reactions of Alcohols

Synthesis (6) – Reactions of Alcohols

July 27, 2015

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 […]

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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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Demystifying Alcohol Oxidations

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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Alcohol Oxidation: “Strong” and “Weak” Oxidants

Alcohol Oxidation: “Strong” and “Weak” Oxidants

May 6, 2015

Here’s what we’ll talk about today: reagents for the oxidation of alcohols! Oxidations Of Alcohols With “Eye Of Newt”, “Wing of Bat”, and “Powdered Unicorn Horn” Here we are, at least  fifteen articles into this series on alcohols, and all we’ve really talked about is substitution and elimination reactions, with a little bit of acid-base […]

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Elimination of Alcohols To Alkenes With POCl3

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

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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