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Secondary (chemistry)

Term in organic chemistry used to describe degree of substitution of an atom in a molecule

Secondary is a term used in organic chemistry to classify various types of compounds (e. g. alcohols, https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Organic_Chemistry)/Alcohols/Nomenclature_of_Alcohols alkyl halides, amines) or reactive intermediates (e. g. alkyl radicals, carbocations). An atom is considered secondary if it has two 'R' Groups attached to it. An 'R' group is a carbon containing group such as a methyl (CH3). A secondary compound is most often classified on an alpha carbon (middle carbon) or a nitrogen. The word secondary comes from the root word 'second' which means two.

Carbon atom in an alkane	[[File:Prim. Hydrocarbon Structural Formulae V.1.png	80px	frameless]]	[[File:Sec. Hydrocarbon Structural Formulae V.1.png	80px	frameless]]	[[File:Tert. Hydrocarbon Structural Formulae V.1.png	80px	frameless]]	[[File:Quart. Hydrocarbon Structural Formulae V.1.png	80px	frameless]]

This nomenclature can be used in many cases and further used to explain relative reactivity. The reactivity of molecules varies with respect to the attached atoms. Thus, a primary, secondary, tertiary and quaternary molecule of the same function group will have different reactivities.

Secondary alcohols

Secondary alcohols have the formula RCH(OH)R' where R and R' are organyl.

Alcohol	[[File:Prim. Alcohol Structural Formulae V.1.png	90px	frameless]]	[[File:Sec. Alcohol Structural Formulae V.1.png	90px	frameless]]	[[File:Tert. Alcohol Structural Formulae V.1.png	90px	frameless]]	does not exist

Secondary amines

A secondary amine has the formula RR'NH where R and R' are organyl.

Amine	[[File:Prim. Amine Structural Formulae V.1.png	70px	frameless]]	[[File:Sec. Amine Structural Formulae V.1.png	70px	frameless]]	[[File:Tert. Amine Structural Formulae V.1.png	70px	frameless]]	[[File:Quarternary ammonium cation Structural Formula V.1.png	70px	frameless]]

Secondary amides

Secondary amides have the formula RC(O)NHR' where R can be H or organyl and R' is organyl. which is the loss of the single proton bonded to the middle nitrogen.

Amide	[[File:Prim. Amide Structural Formulae V.1.png	100px	frameless]]	[[File:Sec. Amide Structural Formulae V.1.png	100px	frameless]]	[[File:Tert. Amide Structural Formulae V.1.png	100px	frameless]]	does not exist

Secondary phosphines

Secondary phosphines have two 'R' groups attached to a phosphorus atom and again, a P-H bond.

Phosphine	[[File:Prim. Phosphine Structural Formulae V.1.png	70px	frameless]]	[[File:Sec. Phosphine Structural Formulae V.1.png	70px	frameless]]	[[File:Tert. Phosphine Structural Formulae V.1.png	70px	frameless]]	[[File:Quart. Phosphonium Cation Structural Formulae V.1.png	70px	frameless]]

Further uses

"Secondary" is a general term used in chemistry that can be applied to many molecules, even more than the ones listed here; the principles seen in these examples can be further applied to other functional group containing molecules. The ones shown above are common molecules seen in many organic reactions. By classifying a molecule as secondary it then be compared with a molecule of primary or tertiary nature to determine the relative reactivity.

References

"alcohol - Structure and classification of alcohols {{!}} Britannica".
(November 2014). "Synthesis, reactivity, and coordination chemistry of secondary phosphines". Coordination Chemistry Reviews.
Ashenhurst, James. (2010-06-16). "Primary, Secondary, Tertiary, Quaternary In Organic Chemistry".

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