Organic Reagents

The E2 Mechanism

September 27, 2012

Having gone through the E1 mechanism for elimination reactions, we’ve accounted for one way in which elimination reactions can occur. However, there’s still another set of data that describes some elimination reactions that we haven’t adequately explained yet. Here’s an example of the reaction I’m talking about: What’s interesting about this reaction is that it [...]

Tagged as: anti, base, e2, elimination, kinetics, stereochemistry, zaitsev's rule

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Reaction Friday: Conversion of Alcohols to Alkyl Chlorides With SOCl2

March 10, 2012

Treatment of alcohols with thionyl chloride (SOCl2) converts alcohols to alkyl chlorides. When the reaction is performed on secondary alcohols with a stereocenter, the reaction proceeds with inversion of configuration. Related Posts:Introducing the Reaction GuideOrganic Reaction Flashcards Version 2.0 Is Here! Why Organic Chemistry Made Me Feel DumbThe latest version of Reagents contains a “social [...]

Tagged as: Reaction Friday, reaction guide, reagents, socl2, thionyl chloride

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Reagent Friday: Zinc Amalgam (Zn-Hg)

December 9, 2011

In a blatant plug for the Reagent Guide and the Reagents App for iPhone, each Friday  I profile a different reagent that is commonly encountered in Org 1/ Org 2.  What it’s used for: For our purposes, zinc amalgam has one important use: in the Clemmensen reduction of ketones to alkanes. Similar to: The reagent has essentially the same [...]

Tagged as: acid, aromatic chemistry, clemmensen, Reagent guide, reagents, reagents app, reduction, zn(hg)

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Reagent Friday: Thionyl Chloride (SOCl2)

December 3, 2011

In a blatant plug for the Reagent Guide and the Reagents App for iPhone, each Friday  I profile a different reagent that is commonly encountered in Org 1/ Org 2.  If there’s one thing you learn how to do well in Org 1, it’s make alcohols. Let’s count the ways: hydroboration, acid-catalyzed hydration, oxymercuration for starters, and then substitution [...]

Tagged as: alcohols, alkyl chlorides, alkyl halides, inversion, reagent friday, SN2, socl2

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Reagent Friday: Palladium on Carbon (Pd/C)

November 25, 2011

In a blatant plug for the Reagent Guide and the Reagents App for iPhone, each Friday  I profile a different reagent that is commonly encountered in Org 1/ Org 2.  It’s almost been 100 years since Paul Sabatier was awarded the 1912 Nobel prize for his discovery that hydrogen gas will add to alkenes (among other molecules, such as [...]

Tagged as: alkenes, H2, hydrogenation, pd/c, reagent friday, reduction, stereoselective

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Reagent Friday: LiAlH[OC(CH3)3]3

November 11, 2011

In a blatant plug for the Reagent Guide and the Reagents App for iPhone, each Friday  I profile a different reagent that is commonly encountered in Org 1/ Org 2.  Today’s reagent is probably a bit on the obscure side, but it solves a useful problem. Lithium tri tert-butoxy aluminum hydride is lot like lithium aluminum hydride, but with [...]

Tagged as: acid halides, alcohols, bulky, esters, hydrides, LiAlHOtBu3, Reagent guide, reagents app, reducing agents

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Reagent Friday – Diazomethane (CH2N2)

November 5, 2011

In a blatant plug for the Reagent Guide and the Reagents App for iPhone, each Friday  I profile a different reagent that is commonly encountered in Org 1/ Org 2.  One of the things about learning organic chemistry from a textbook is that about 98% of you will never really have to consider the practical aspects of working with [...]

Tagged as: carboxylic acids, ch2n2, diazomethane, esterification, reagent friday, Reagent guide, reagents

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Reagent Friday: Potassium t-butoxide [KOC(CH3)3]

October 29, 2011

In a blatant plug for the Reagent Guide and the Reagents App for iPhone, each Friday  I profile a different reagent that is commonly encountered in Org 1/ Org 2.  Sometime back in general chemistry you (hopefully) learned that hydroxide ion (HO-) is a strong base. It’s the conjugate base of water – that is to say, that’s what’s [...]

Tagged as: alkenes, bulky bases, hoffman, KOtBu, NaOtBu, reagent friday, Reagent guide, reagents app, steric hindrance, t-butoxide, zaitsev

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Reagent Friday: Sodium Periodate

October 21, 2011

In a blatant plug for the Reagent Guide and the Reagents App for iPhone, each Friday  I profile a different reagent that is commonly encountered in Org 1/ Org 2.  In organic chemistry, sometimes you need to build molecules up. Other times, you need to break molecules down. Ozone, which we talked about earlier, is a really useful reagent [...]

Tagged as: aldehydes, cleavage, diols, naIO4, oxidation, reagent friday, Reagent guide, reagents app

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Reagent Friday: Grignard Reagents

October 14, 2011

In a blatant plug for the Reagent Guide and the Reagents App for iPhone, each Friday  I profile a different reagent that is commonly encountered in Org 1/ Org 2.  NOTE - I said that the Reagents app wouldn’t be free forever. Today’s the last day to pick up the Reagents app for free from the App Store! Get it [...]