In
organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J.; ...
, acid hydrolysis is a
hydrolysis
Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...
process in which a
protic acid is used to
catalyze
Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...
the cleavage of a chemical bond via a
nucleophilic substitution
In chemistry, a nucleophilic substitution is a class of chemical reactions in which an electron-rich chemical species (known as a nucleophile) replaces a functional group within another electron-deficient molecule (known as the electrophile). The ...
reaction, with the addition of the elements of water (H
2O). For example, in the conversion of
cellulose
Cellulose is an organic compound with the formula , a polysaccharide consisting of a linear chain of several hundred to many thousands of β(1→4) linked D-glucose units. Cellulose is an important structural component of the primary cell wall ...
or
starch
Starch or amylum is a polymeric carbohydrate consisting of numerous glucose units joined by glycosidic bonds. This polysaccharide is produced by most green plants for energy storage. Worldwide, it is the most common carbohydrate in human diets ...
to
glucose
Glucose is a simple sugar with the molecular formula . Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using ...
. For the case of
esters
In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides are ...
and
amides
In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula , where R, R', and R″ represent organic groups or hydrogen atoms. The amide group is called a peptide bond when it is ...
, it can be defined as an acid catalyzed
nucleophilic acyl substitution
Nucleophilic acyl substitution describe a class of substitution reactions involving nucleophiles and acyl compounds. In this type of reaction, a nucleophile – such as an alcohol, amine, or enolate – displaces the leaving group of an acyl deriv ...
reaction.
The term is also applied to certain
nucleophilic addition
In organic chemistry, a nucleophilic addition reaction is an addition reaction where a chemical compound with an electrophilic double or triple bond reacts with a nucleophile, such that the double or triple bond is broken. Nucleophilic additions di ...
reactions, such as in the acid catalyzed hydrolysis of
nitriles
In organic chemistry, a nitrile is any organic compound that has a functional group. The prefix ''cyano-'' is used interchangeably with the term ''nitrile'' in industrial literature. Nitriles are found in many useful compounds, including met ...
to amides. Acid hydrolysis ''does not'' usually refer to the acid catalyzed addition of the elements of water to double or triple bonds by
electrophilic addition
In organic chemistry, an electrophilic addition reaction is an addition reaction where a chemical compound containing a double or triple bond has a π bond broken, with the formation of two new σ bonds.March, Jerry; (1985). Advanced Organic Che ...
as may originate from a
hydration reaction
In chemistry, a hydration reaction is a chemical reaction
A chemical reaction is a process that leads to the IUPAC nomenclature for organic transformations, chemical transformation of one set of chemical substances to another. Classically, che ...
.
Acid hydrolysis is used to prepare monosaccharide with the help of acids, such as:
* Hydrochloric acid
* Sulfuric acid
* Trifluoroacetic acid
* Formic acid
* Nitric acid
Acid hydrolysis can be utilized in the pretreatment of cellulosic material, so as to cut the interchain linkages in hemicellulose and cellulose.
See also
*
Alkaline hydrolysis
Alkaline hydrolysis, in organic chemistry, usually refers to types of nucleophilic substitution reactions in which the attacking nucleophile is a hydroxide ion.
Example
In the alkaline hydrolysis of esters and amides the hydroxide ion nucleophi ...
*
Enzymatic hydrolysis
In biochemistry, enzymatic hydrolysis is a process in which enzymes facilitate the cleavage of bonds in molecules with the addition of the elements of water (i.e. hydrolysis). It plays an important role in the digestion of food.
It may be used t ...
*
Acid catalysis
In acid catalysis and base catalysis, a chemical reaction is catalyzed by an acid or a base. By Brønsted–Lowry acid–base theory, the acid is the proton (hydrogen ion, H+) donor and the base is the proton acceptor. Typical reactions catalyze ...
References
{{DEFAULTSORT:Acid Hydrolysis
Chemical reactions