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The Burgess reagent (methyl N-(triethylammoniumsulfonyl)carbamate) is a mild and selective dehydrating reagent often used in organic chemistry. [1] [2] It was developed in the laboratory of Edward M. Burgess at Georgia Tech. The Burgess reagent is used to convert secondary and tertiary alcohols with an adjacent proton into alkenes. Dehydration ...
The classic example of a dehydration reaction is the Fischer esterification, which involves treating a carboxylic acid with an alcohol to give an ester RCO 2 H + R′OH ⇌ RCO 2 R′ + H 2 O Often such reactions require the presence of a dehydrating agent, i.e. a substance that reacts with water.
In organic synthesis, the 2-tetrahydropyranyl (THP) group is used as a protecting group for alcohols. [3] [4] Reaction of the alcohol with DHP forms a THP ether, protecting the alcohol from a variety of reactions. The alcohol can later be restored by acidic hydrolysis, concomitant with formation of 5-hydroxypentanal. [5]
The compound is a reagent in organic synthesis. One application is for the dehydration of a secondary alcohol to give an alkene: [2] RCH(OH)CH 2 R' + Ph 2 S[OC(CF 3) 2 Ph] 2 → RCH=CHR' + Ph 2 SO + 2 HOC(CF 3) 2 Ph Mechanism of the dehydration using Martin's sulfurane.
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The term aldol condensation is also commonly used, especially in biochemistry, to refer to just the first (addition) stage of the process—the aldol reaction itself—as catalyzed by aldolases. However, the first step is formally an addition reaction rather than a condensation reaction because it does not involve the loss of a small molecule.
Another water molecule comes along and takes up the extra proton. This reaction tends to yield many undesirable side products, (for example diethyl ether in the process of creating ethanol) and in its simple form described here is not considered very useful for the production of alcohol. Two approaches are taken.
The alcohol is protonated, the H 2 O group formed leaves, forming a carbocation, and the nucleophile Cl − (which is present in excess) readily attacks the carbocation, forming the chloroalkane. Tertiary alcohols react immediately with Lucas reagent as evidenced by turbidity owing to the low solubility of the organic chloride in the aqueous ...