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

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

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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The SN1, E1, and Alkene Addition Reactions All Pass Through A Carbocation Intermediate

April 21, 2015

Was going to include this in my last post but it was getting too big. Note how the SN1, E1, and alkene addition reactions all pass through a carbocation intermediate. Here’s how they’re related. Starting with an alkene, adding strong acid gets us to a carbocation (A–>B). If the counterion to that acid is a […]

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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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In Speech, Obama Expresses Concern Over Growing Electron Inequality

In Speech, Obama Expresses Concern Over Growing Electron Inequality

April 1, 2015

WASHINGTON – In a speech at a black-tie meeting of the Periodic Table of the Elements last night, President Obama called on all atoms to share their electrons more equally. “Electron inequality represents the biggest problem that atoms face today. Disturbingly, chemistry has increasingly become divided into two groups: the electron “haves” and the electron “have-nots”. “Folks with the […]

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Weirdest spam comment I’ve had in awhile

Weirdest spam comment I’ve had in awhile

March 23, 2015

In the “WTF” category…   Author : Dr abdoul E-mail : cleaninglabyahoocom URL : http://www.cleaninglab.ga Comment: WELCOME TO CLEANINGLAB LABORATORIES (PTY) LTD. WE PROVIDE SSD SOLUTION CHEMICAL FOR CLEANING BLACK MONEY HI,THIS IS JUST TO INFORM YOU THAT OUR COMPANY CAN CLEAN OUT BLACK MONEY CALLED ANTI-BREEZE (STAINED MONEY) BANK NOTES SO PLEASE IF YOU […]

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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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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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