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, ...
, ortho acids are
organic,
hypothetical compound
A hypothetical chemical compound is a chemical compound that has been conceived of, but is not known to have been synthesized, observed, or isolated (identified or shown to exist).
Some hypothetical compounds cannot form at all. Others might tur ...
s having the structure (R =
alkyl
In organic chemistry, an alkyl group is an alkane missing one hydrogen.
The term ''alkyl'' is intentionally unspecific to include many possible substitutions.
An acyclic alkyl has the general formula of . A cycloalkyl is derived from a cycloa ...
or
aryl
In organic chemistry, an aryl is any functional group or substituent derived from an aromaticity, aromatic ring, usually an aromatic hydrocarbon, such as phenyl and naphthyl. "Aryl" is used for the sake of abbreviation or generalization, and "Ar ...
).
Ortho acids themselves are unstable and cannot be isolated. However,
orthoester
In organic chemistry, an ortho ester is a functional group containing three alkoxy groups attached to one carbon atom, i.e. with the general formula . Orthoesters may be considered as products of exhaustive alkylation of unstable orthocarboxylic ...
s can be synthesized by the
Pinner reaction
The Pinner reaction refers to the acid catalysed reaction of a nitrile with an alcohol to form an imino ester salt (alkyl imidate salt); this is sometimes referred to as a Pinner salt.
The reaction is named after Adolf Pinner, who first describ ...
, in which
nitriles react with
alcohols under acid catalysis:
:
RCN + 3 R'OH -> RC(OR')3 + NH3
Historic definition
Historically the prefixes "''hypo''-", "''per''-", "''ortho''-", "''
meta-
Meta (from the Greek μετά, ''meta'', meaning "after" or "beyond") is a prefix meaning "more comprehensive" or "transcending".
In modern nomenclature, ''meta''- can also serve as a prefix meaning self-referential, as a field of study or endea ...
''", and "''pyro''-" were used to distinguish between different
oxyacid
An oxyacid, oxoacid, or ternary acid is an acid that contains oxygen. Specifically, it is a compound that contains hydrogen, oxygen, and at least one other element, with at least one hydrogen atom bonded to oxygen that can dissociate to produce ...
s of the same element, of these ortho acid is the most highly
oxidised
Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a d ...
or
hydroxylated. For example,
dehydration
In physiology, dehydration is a lack of total body water, with an accompanying disruption of metabolic processes. It occurs when free water loss exceeds free water intake, usually due to exercise, disease, or high environmental temperature. Mil ...
of
orthoperiodic acid
Periodic acid ( ) is the highest oxoacid of iodine, in which the iodine exists in oxidation state +7. Like all periodates it can exist in two forms: orthoperiodic acid, with the chemical formula , and metaperiodic acid, which has the formula .
...
gives
metaperiodic acid
Periodic acid ( ) is the highest oxoacid of iodine, in which the iodine exists in oxidation state +7. Like all periodates it can exist in two forms: orthoperiodic acid, with the chemical formula , and metaperiodic acid, which has the formula .
...
. Such naming conventions are now obsolete; however, various traditional names containing these prefixes have been retained in
IUPAC nomenclature
A chemical nomenclature is a set of rules to generate systematic names for chemical compounds. The nomenclature used most frequently worldwide is the one created and developed by the International Union of Pure and Applied Chemistry (IUPAC).
T ...
(e.g.
orthosilicic acid
Orthosilicic acid () is an inorganic compound with the formula . Although rarely observed, it is the key compound of silica and silicates and the precursor to other silicic acids . Silicic acids play important roles in biomineralization and ...
(),
orthotelluric acid () and
orthophosphoric acid
Phosphoric acid (orthophosphoric acid, monophosphoric acid or phosphoric(V) acid) is a colorless, odorless phosphorus-containing solid, and inorganic compound with the chemical formula . It is commonly encountered as an 85% aqueous solution, w ...
().
See also
*
Orthoacetic acid
References
Acids
Chemical nomenclature
Hypothetical chemical compounds
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