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The conversion of ethanol to ethylene is a fundamental example: [3] [4] CH 3 CH 2 OH → H 2 C=CH 2 + H 2 O. The reaction is accelerated by acid catalysts such as sulfuric acid and certain zeolites. These reactions often proceed via carbocation intermediates as shown for the dehydration of cyclohexanol. [5] Some alcohols are prone to dehydration.
The carbon snake is a demonstration of the dehydration reaction of sugar by concentrated sulfuric acid. With concentrated sulfuric acid, granulated table sugar ( sucrose ) performs a degradation reaction which changes its form to a black solid-liquid mixture . [ 1 ]
The reaction, in general, obeys Zaitsev's Rule, which states that the most stable (usually the most substituted) alkene is formed. Tertiary alcohols are eliminated easily at just above room temperature, but primary alcohols require a higher temperature. This is a diagram of acid catalyzed dehydration of ethanol to produce ethylene:
The reaction may otherwise involve the functional groups of the molecule, and is a versatile class of reactions that can occur in acidic or basic conditions or in the presence of a catalyst. This class of reactions is a vital part of life as it is essential to the formation of peptide bonds between amino acids and to the biosynthesis of fatty ...
For example, DNA ligase can join two complementary fragments of nucleic acid by forming phosphodiester bonds, and repair single stranded breaks that arise in double stranded DNA during replication. In general, a ligase catalyzes the following dehydration reaction, thus joining molecules A and B: A-OH + B-H → A–B + H 2 O
The dehydration of secondary and tertiary alcohols to yield an olefin through a sulfamate ester intermediate is called the Burgess dehydration reaction. [ 13 ] [ 14 ] [ 15 ] The reaction conditions used are typically very mild, giving it some advantage over other dehydration methods for sensitive substrates.
A Knoevenagel condensation is a nucleophilic addition of an active hydrogen compound to a carbonyl group followed by a dehydration reaction in which a molecule of water is eliminated (hence condensation). The product is often an α,β-unsaturated ketone (a conjugated enone). General Knoevenagel layout
Another useful example is the one pot two-step synthesis of halfordinol, a parent compound for Rutaceae alkaloids. The initial steps follow the Fischer oxazole synthesis, although the acid-catalyzed cyclization occurs in two steps rather than one, which ensures the formation of the di-chloro intermediate , preventing formation of the regioisomer .