Alcohols Can Act As Acids Or Bases (And Why It Matters)
Alcohols: The Conjugate Acid Is A Better Leaving Group, and The Conjugate Base Is A Better Nucleophile In the last post we explored some of the properties and
Read moreAlcohols – Acidity and Basicity
Acid-Base Reactions Of Alcohols Alcohols are mild acids. Typical aliphatic (i.e. “alkyl”) alcohols such as ethanol, isopropanol, and t-butanol have a pKa of about 16-18, making
Read moreThe Williamson Ether Synthesis
The Williamson Ether Synthesis In the Williamson Ether Synthesis, an alkyl halide (or sulfonate, such as a tosylate or mesylate) undergoes nucleophilic substitution (SN2) by an alkoxide to give an ether.
Read moreEthers From Alkenes, Tertiary Alkyl Halides and Alkoxymercuration
When The Williamson Doesn’t Work: Synthesis of Tertiary Ethers From Alkenes, SN1 Reactions, and Alkoxymercuration In the last two posts we’ve been discussing the Williamson
Read moreAlcohols To Ethers via Acid Catalysis
How To Make Ethers With Alcohols And Acid Symmetrical ethers can be made from the acid-catalyzed dehydration of primary alcohols. A classic example is the
Read moreRearrangement Reactions (1) – Hydride Shifts
Rearrangement Reactions: Substitution Reactions With Hydride Shifts In this post we cover several examples of reactions where carbocations form… but then a funny thing happens.
Read moreCleavage Of Ethers With Acid
Acidic Cleavage of Ethers Can Proceed Through an SN2 or SN1 Mechanism, Depending On The Structure Ethers do not undergo very many reactions. One key
Read moreIn Speech, Obama Expresses Concern Over Growing Electron Inequality
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
Read moreEpoxides – The Outlier Of The Ether Family
Properties and Synthesis of Epoxides Epoxides (oxiranes) are cyclic ethers that have unusually high reactivity due to ring strain (about 25 kcal/mol). The 3-membered ring
Read moreOpening of Epoxides With Acid
Opening Epoxides With Aqueous Acid Epoxides can undergo ring-opening with nucleophiles under acidic conditions. In this reaction, the epoxide oxygen is protonated first, making it
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