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Due to the high chemical stability of ethers, the cleavage of the C-O bond is uncommon in the absence of specialized reagents or under extreme conditions. [1] [2] In organic chemistry, ether cleavage is an acid catalyzed nucleophilic substitution reaction. Depending on the specific ether, cleavage can follow either S N 1 or S N 2 mechanisms.
The benzilic acid rearrangement is formally the 1,2-rearrangement of 1,2-diketones to form α-hydroxy–carboxylic acids using a base.This reaction receives its name from the reaction of benzil with potassium hydroxide to form benzilic acid.
Benzylic cations of chromium arene complexes are conformationally stable, and undergo only exo attack to afford S N 1 products stereospecifically, with retention of configuration. [1] Propargyl [ 1 ] and oxonium [ 1 ] cations undergo retentive substitution reactions, and even β carbocations react with a significant degree of retention.
For example, (C 6 H 5)(CH 3) 2 C + is referred to as a "benzylic" carbocation. The benzyl free radical has the formula C 6 H 5 CH 2 •. The benzyl cation or phenylcarbenium ion is the carbocation with formula C 6 H 5 CH + 2; the benzyl anion or phenylmethanide ion is the carbanion with the formula C 6 H 5 CH − 2.
Reductions with hydrosilanes are methods used for hydrogenation and hydrogenolysis of organic compounds.The approach is a subset of ionic hydrogenation.In this particular method, the substrate is treated with a hydrosilane and auxiliary reagent, often a strong acid, resulting in formal transfer of hydride from silicon to carbon. [1]
A carbocation is an ion with a positively charged carbon atom. Among the simplest examples are the methenium CH + 3, methanium CH + 5, acylium ions RCO +, and vinyl C ...
HSAB is widely used in chemistry for explaining the stability of compounds, reaction mechanisms and pathways. It assigns the terms 'hard' or 'soft', and 'acid' or 'base' to chemical species . 'Hard' applies to species which are small, have high charge states (the charge criterion applies mainly to acids, to a lesser extent to bases), and are ...
The driving force for this rearrangement step is believed to be the relative stability of the resultant oxonium ion. Although the initial carbocation is already tertiary, the oxygen can stabilize the positive charge much more favorably due to the complete octet configuration at all centers.