Hydroalkoxylation is a chemical reaction that combines
alcohol
Alcohol most commonly refers to:
* Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom
* Alcohol (drug), an intoxicant found in alcoholic drinks
Alcohol may also refer to:
Chemicals
* Ethanol, one of sev ...
s with
alkene
In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond.
Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, an ...
s or
alkyne
\ce
\ce
Acetylene
\ce
\ce
\ce
Propyne
\ce
\ce
\ce
\ce
1-Butyne
In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and n ...
s. The process affords
ether
In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again be c ...
s.
The reaction converts alkenes to dialkyl or aryl-alkyl ethers:
:R'OH + RCH=CH
2 → R'OCH(R)-CH
3
Similarly, alkynes are converted to
vinyl
Vinyl may refer to:
Chemistry
* Polyvinyl chloride (PVC), a particular vinyl polymer
* Vinyl cation, a type of carbocation
* Vinyl group, a broad class of organic molecules in chemistry
* Vinyl polymer, a group of polymers derived from vinyl m ...
ethers:
:R'OH + RC≡CH → R'OC(R)=CH
2
As shown, the reaction follows the
Markovnikov rule
In organic chemistry, Markovnikov's rule or Markownikoff's rule describes the outcome of some addition reactions. The rule was formulated by Russian chemist Vladimir Markovnikov in 1870.
Explanation
The rule states that with the addition of a p ...
. The process exhibits good
atom-economy
Atom economy (atom efficiency/percentage) is the conversion efficiency of a chemical process in terms of all atoms involved and the desired products produced. The simplest definition was introduced by Barry Trost in 1991 and is equal to the ratio ...
in the sense that no byproducts are produced. The reaction is catalyzed by bases and also by transition metal complexes. Usually symmetrical ethers are prepared by dehydration of alcohols and unsymmetrical ethers by the
Williamson ether synthesis
The Williamson ether synthesis is an organic reaction, forming an ether from an organohalide and a deprotonated alcohol (alkoxide). This reaction was developed by Alexander Williamson in 1850. Typically it involves the reaction of an alkoxide io ...
from alkyl halides and alkali metal alkoxides.
[Wilhelm Heitmann, Günther Strehlke, Dieter Mayer "Ethers, Aliphatic" ''Ullmann's Encyclopedia of Industrial Chemistry'' 2002, Wiley-VCH, Weinheim. {{doi, 10.1002/14356007.a10_023]
See also
*
Hydroamination
In organic chemistry, hydroamination is the addition of an bond of an amine across a carbon-carbon multiple bond of an alkene, alkyne, diene, or allene. In the ideal case, hydroamination is atom economical and green. Amines are common in fine-c ...
*
Hydrofunctionalization A hydrofunctionalization reaction is the addition of hydrogen and another univalent fragment (X) across a carbon-carbon or carbon-heteroatom multiple bond. Often, the term ''hydrofunctionalization'' without modifier refers specifically to the use o ...
References
Addition reactions
Homogeneous catalysis
Catalysis