Homologous series

Last updated

In organic chemistry, a homologous series is a sequence of compounds with the same functional group and similar chemical properties in which the members of the series can be branched or unbranched, or differ by molecular formula of CH2 and molecular mass of 14u. [1] This can be the length of a carbon chain, [1] for example in the straight-chained alkanes (paraffins), or it could be the number of monomers in a homopolymer such as amylose. [2] A homologue (also spelled as homolog) is a compound belonging to a homologous series. [3]

Contents

Compounds within a homologous series typically have a fixed set of functional groups that gives them similar chemical and physical properties. (For example, the series of primary straight-chained alcohols has a hydroxyl at the end of the carbon chain.) These properties typically change gradually along the series, and the changes can often be explained by mere differences in molecular size and mass. The name "homologous series" is also often used for any collection of compounds that have similar structures or include the same functional group, such as the general alkanes (straight and branched), the alkenes (olefins), the carbohydrates, etc. However, if the members cannot be arranged in a linear order by a single parameter, the collection may be better called a "chemical family" or "class of homologous compounds" than a "series".

The concept of homologous series was proposed in 1843 by the French chemist Charles Gerhardt. [4] A homologation reaction is a chemical process that converts one member of a homologous series to the next member.

Examples

The homologous series of straight-chained alkanes begins methane (CH4), ethane (C2H6), propane (C3H8), butane (C4H10), and pentane (C5H12). In that series, successive members differ in mass by an extra methylene bridge (-CH2- unit) inserted in the chain. Thus the molecular mass of each member differs by 14 atomic mass units. Adjacent members in such a series, such as methane and ethane, are known as "adjacent homologues". [5]

Normal boiling points of straight chain alkanes Alkane boilingpoints (centigrade) from methane to nonadecane.png
Normal boiling points of straight chain alkanes

Within that series, many physical properties such as boiling point gradually change with increasing mass. For example, ethane (C2H6), has a higher boiling point than methane (CH4). This is because the London dispersion forces between ethane molecules are higher than that between methane molecules, resulting in stronger forces of intermolecular attraction, raising the boiling point.

L-Serin - L-Serine.svg
L-Homoserin.svg
Serine and homoserine are homologues.

Some important classes of organic molecules are derivatives of alkanes, such as the primary alcohols, aldehydes, and (mono)carboxylic acids form analogous series to the alkanes. The corresponding homologous series of primary straight-chained alcohols comprises methanol (CH4O), ethanol (C2H6O), 1-propanol (C3H8O), 1-butanol, and so on. The single-ring cycloalkanes form another such series, starting with cyclopropane.

Homologous seriesGeneral formulaRepeating unitFunctional group(s)
Straight-chain alkanes CnH2n + 2 (n ≥ 1) −CH2 H3C− ... −CH3
Straight-chain perfluoroalkanes CnF2n + 2 (n ≥ 1) −CF2 F3C− ... −CF3
Straight-chain alkyl CnH2n + 1 (n ≥ 1)−CH2H3C− ... −CH2
Straight-chain 1-alkenes CnH2n (n ≥ 2)−CH2 H2C=C− ... −CH3
Cycloalkanes CnH2n (n ≥ 2)−CH2Singly-bonded ring
Straight-chain 1-alkynes CnH2n − 2 (n ≥ 2)−CH2 HC≡C− ... −CH3
polyacetylenes C2nH2n + 2 (n ≥ 2) −CH=CH− H3C− ... −CH3
Straight-chain primary alcohols CnH2n + 1OH (n ≥ 1)−CH2H3C− ... −OH
Straight-chain primary monocarboxylic acids CnH2n + 1COOH (n ≥ 0)−CH2H3C− ... −COOH
Straight-chain azanes NnHn + 2 (n ≥ 1)−NH−H2N− ... −NH2

Biopolymers also form homologous series, for example the polymers of glucose such as cellulose oligomers [6] starting with cellobiose, or the series of amylose oligomers starting with maltose, which are sometimes called maltooligomers. [7] Homooligopeptides, oligopeptides made up of repetitions of only one amino acid can also be studied as homologous series. [8]

Inorganic homologous series

Homologous series are not unique to organic chemistry. Titanium, vanadium, and molybdenum oxides all form homologous series (e.g. VnO2n − 1 for 2 < n < 10), called Magnéli phases, [9] as do the silanes, SinH2n + 2 (with n up to 8) that are analogous to the alkanes, CnH2n + 2.

Periodic table

On the periodic table, homologous elements share many electrochemical properties and appear in the same group (column) of the table. For example, all noble gases are colorless, monatomic gases with very low reactivity. These similarities are due to similar structure in their outer shells of valence electrons. [10] Mendeleev used the prefix eka- for an unknown element below a known one in the same group.

See also

Related Research Articles

<span class="mw-page-title-main">Alkane</span> Type of saturated hydrocarbon compound

In organic chemistry, an alkane, or paraffin, is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in which all the carbon–carbon bonds are single. Alkanes have the general chemical formula CnH2n+2. The alkanes range in complexity from the simplest case of methane, where n = 1, to arbitrarily large and complex molecules, like pentacontane or 6-ethyl-2-methyl-5-(1-methylethyl) octane, an isomer of tetradecane.

<span class="mw-page-title-main">Aliphatic compound</span> Hydrocarbon compounds without aromatic rings

In organic chemistry, hydrocarbons are divided into two classes: aromatic compounds and aliphatic compounds. Aliphatic compounds can be saturated like hexane, or unsaturated, like hexene and hexyne. Open-chain compounds, whether straight or branched, and which contain no rings of any type, are always aliphatic. Cyclic compounds can be aliphatic if they are not aromatic.

In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, such as parentheses, dashes, brackets, commas and plus (+) and minus (−) signs. These are limited to a single typographic line of symbols, which may include subscripts and superscripts. A chemical formula is not a chemical name since it does not contain any words. Although a chemical formula may imply certain simple chemical structures, it is not the same as a full chemical structural formula. Chemical formulae can fully specify the structure of only the simplest of molecules and chemical substances, and are generally more limited in power than chemical names and structural formulae.

<span class="mw-page-title-main">Hydrocarbon</span> Organic compound consisting entirely of hydrogen and carbon

In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic; their odor is usually faint, and may be similar to that of gasoline or lighter fluid. They occur in a diverse range of molecular structures and phases: they can be gases, liquids, low melting solids or polymers.

In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula CH3. In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many organic compounds. It is a very stable group in most molecules. While the methyl group is usually part of a larger molecule, bounded to the rest of the molecule by a single covalent bond, it can be found on its own in any of three forms: methanide anion, methylium cation or methyl radical. The anion has eight valence electrons, the radical seven and the cation six. All three forms are highly reactive and rarely observed.

<span class="mw-page-title-main">Organic chemistry</span> Subdiscipline of chemistry, focusing on carbon compounds

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. Study of structure determines their structural formula. Study of properties includes physical and chemical properties, and evaluation of chemical reactivity to understand their behavior. The study of organic reactions includes the chemical synthesis of natural products, drugs, and polymers, and study of individual organic molecules in the laboratory and via theoretical study.

<span class="mw-page-title-main">Wax</span> Class of organic compounds which are malleable at room temperature

Waxes are a diverse class of organic compounds that are lipophilic, malleable solids near ambient temperatures. They include higher alkanes and lipids, typically with melting points above about 40 °C (104 °F), melting to give low viscosity liquids. Waxes are insoluble in water but soluble in nonpolar organic solvents such as hexane, benzene and chloroform. Natural waxes of different types are produced by plants and animals and occur in petroleum.

<span class="mw-page-title-main">Haloalkane</span> Group of chemical compounds derived from alkanes containing one or more halogens

The haloalkanes are alkanes containing one or more halogen substituents. They are a subset of the general class of halocarbons, although the distinction is not often made. Haloalkanes are widely used commercially. They are used as flame retardants, fire extinguishants, refrigerants, propellants, solvents, and pharmaceuticals. Subsequent to the widespread use in commerce, many halocarbons have also been shown to be serious pollutants and toxins. For example, the chlorofluorocarbons have been shown to lead to ozone depletion. Methyl bromide is a controversial fumigant. Only haloalkanes that contain chlorine, bromine, and iodine are a threat to the ozone layer, but fluorinated volatile haloalkanes in theory may have activity as greenhouse gases. Methyl iodide, a naturally occurring substance, however, does not have ozone-depleting properties and the United States Environmental Protection Agency has designated the compound a non-ozone layer depleter. For more information, see Halomethane. Haloalkane or alkyl halides are the compounds which have the general formula "RX" where R is an alkyl or substituted alkyl group and X is a halogen.

<span class="mw-page-title-main">Ethane</span> Organic compound (H3C–CH3)

Ethane is an organic chemical compound with chemical formula C
2
H
6
. At standard temperature and pressure, ethane is a colorless, odorless gas. Like many hydrocarbons, ethane is isolated on an industrial scale from natural gas and as a petrochemical by-product of petroleum refining. Its chief use is as feedstock for ethylene production.

<span class="mw-page-title-main">Cycloalkane</span> Saturated alicyclic hydrocarbon

In organic chemistry, the cycloalkanes are the monocyclic saturated hydrocarbons. In other words, a cycloalkane consists only of hydrogen and carbon atoms arranged in a structure containing a single ring, and all of the carbon-carbon bonds are single. The larger cycloalkanes, with more than 20 carbon atoms are typically called cycloparaffins. All cycloalkanes are isomers of alkenes.

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 −CnH2n+1. A cycloalkyl group is derived from a cycloalkane by removal of a hydrogen atom from a ring and has the general formula −CnH2n−1. Typically an alkyl is a part of a larger molecule. In structural formulae, the symbol R is used to designate a generic (unspecified) alkyl group. The smallest alkyl group is methyl, with the formula −CH3.

<span class="mw-page-title-main">Tholin</span> Class of molecules formed by ultraviolet irradiation of organic compounds

Tholins are a wide variety of organic compounds formed by solar ultraviolet or cosmic ray irradiation of simple carbon-containing compounds such as carbon dioxide, methane or ethane, often in combination with nitrogen or water. Tholins are disordered polymer-like materials made of repeating chains of linked subunits and complex combinations of functional groups, typically nitriles and hydrocarbons, and their degraded forms such as amines and phenyls. Tholins do not form naturally on modern-day Earth, but they are found in great abundance on the surfaces of icy bodies in the outer Solar System, and as reddish aerosols in the atmospheres of outer Solar System planets and moons.

In chemical nomenclature, the IUPAC nomenclature of organic chemistry is a method of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry (IUPAC). It is published in the Nomenclature of Organic Chemistry. Ideally, every possible organic compound should have a name from which an unambiguous structural formula can be created. There is also an IUPAC nomenclature of inorganic chemistry.

Organochlorine chemistry is concerned with the properties of organochlorine compounds, or organochlorides, organic compounds containing at least one covalently bonded atom of chlorine. The chloroalkane class includes common examples. The wide structural variety and divergent chemical properties of organochlorides lead to a broad range of names, applications, and properties. Organochlorine compounds have wide use in many applications, though some are of profound environmental concern, with TCDD being one of the most notorious.

<span class="mw-page-title-main">Eclipsed conformation</span> Molecular form in which substituents on two adjacent atoms are closest together

In chemistry an eclipsed conformation is a conformation in which two substituents X and Y on adjacent atoms A, B are in closest proximity, implying that the torsion angle X–A–B–Y is 0°. Such a conformation can exist in any open chain, single chemical bond connecting two sp3-hybridised atoms, and it is normally a conformational energy maximum. This maximum is often explained by steric hindrance, but its origins sometimes actually lie in hyperconjugation.

<span class="mw-page-title-main">Volatility (chemistry)</span> Tendency of a substance to vaporize

In chemistry, volatility is a material quality which describes how readily a substance vaporizes. At a given temperature and pressure, a substance with high volatility is more likely to exist as a vapour, while a substance with low volatility is more likely to be a liquid or solid. Volatility can also describe the tendency of a vapor to condense into a liquid or solid; less volatile substances will more readily condense from a vapor than highly volatile ones. Differences in volatility can be observed by comparing how fast substances within a group evaporate when exposed to the atmosphere. A highly volatile substance such as rubbing alcohol will quickly evaporate, while a substance with low volatility such as vegetable oil will remain condensed. In general, solids are much less volatile than liquids, but there are some exceptions. Solids that sublimate such as dry ice or iodine can vaporize at a similar rate as some liquids under standard conditions.

In chemistry, the carbon-hydrogen bond is a chemical bond between carbon and hydrogen atoms that can be found in many organic compounds. This bond is a covalent, single bond, meaning that carbon shares its outer valence electrons with up to four hydrogens. This completes both of their outer shells, making them stable.

<span class="mw-page-title-main">Binary silicon-hydrogen compounds</span>

Silanes are saturated chemical compounds with the empirical formula SixHy. They are hydrosilanes, a class of compounds that includes compounds with Si−H and other Si−X bonds. All contain tetrahedral silicon and terminal hydrides. They only have Si−H and Si−Si single bonds. The bond lengths are 146.0 pm for a Si−H bond and 233 pm for a Si−Si bond. The structures of the silanes are analogues of the alkanes, starting with silane, SiH4, the analogue of methane, continuing with disilane Si2H6, the analogue of ethane, etc. They are mainly of theoretical or academic interest.

This glossary of chemistry terms is a list of terms and definitions relevant to chemistry, including chemical laws, diagrams and formulae, laboratory tools, glassware, and equipment. Chemistry is a physical science concerned with the composition, structure, and properties of matter, as well as the changes it undergoes during chemical reactions; it features an extensive vocabulary and a significant amount of jargon.

Group 14 hydrides are chemical compounds composed of hydrogen atoms and group 14 atoms.

References

  1. 1 2 Brown, Theodore L. (It was first discovered by an thomos Reddy 1998 scientist); LeMay, H. Eugene (Harold Eugene); Bursten, Bruce Edward (1991). Chemistry: the central science (5th ed.). Englewood Cliffs, NJ: Prentice Hall. pp.  940. ISBN   978-0-13-126202-7. OCLC   21973767.
  2. Saarela, K. (2013-10-22). Macromolecular Chemistry—8: Plenary and Main Lectures Presented at the International Symposium on Macromolecules Held in Helsinki, Finland, 2–7 July 1972. Elsevier. p. 88. ISBN   978-1-4832-8025-7.
  3. "Glossary of Terms Used in Medicinal Chemistry (IUPAC Recommendations 1998)". Archived from the original on 2017-08-25. Retrieved 2007-12-22.
  4. Charles Gerhardt (1843) "Sur la classification chimique des substances organiques" (On the chemical classification of organic substances), Revue scientifique et industrielle, 14 : 580–609. From page 588: "17. Nous appelons substances homologues celles qui jouissent des même propriétés chimiques et dont la composition offre certaines analogies dans les proportions relatives des éléments." (17. We call homologous substances those that have the same chemical properties and whose composition offers certain analogies in the relative proportion of elements.)
  5. See In re Henze, 181 F.2d 196, 201 (CCPA 1950), in which the court stated, "In effect, the nature of homologues and the close relationship the physical and chemical properties of one member of a series bears to adjacent members is such that a presumption of unpatentability arises against a claim directed to a composition of matter, the adjacent homologue of which is old in the art."
  6. Rojas, Orlando J. (2016-02-25). Cellulose Chemistry and Properties: Fibers, Nanocelluloses and Advanced Materials. Springer. ISBN   978-3-319-26015-0.
  7. Advances in Carbohydrate Chemistry and Biochemistry. Academic Press. 1981-06-19. ISBN   978-0-08-056297-1.
  8. Giddings, J. Calvin (1982-08-25). Advances in Chromatography. CRC Press. ISBN   978-0-8247-1868-8.
  9. Schwingenschlögl, U.; Eyert, V. (2004-09-01). "The vanadium Magnéli phases VnO2n-1". Annalen der Physik. 13 (9): 475–510. arXiv: cond-mat/0403689 . doi:10.1002/andp.200410099. ISSN   0003-3804. S2CID   116832557.
  10. Guillermet, A. Fernández; Grimvall, G. (15 July 1989). "Homology of interatomic forces and Debye temperatures in transition metals". Physical Review B. 40 (3): 1521–1527. Bibcode:1989PhRvB..40.1521G. doi:10.1103/PhysRevB.40.1521. PMID   9992004.