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Though technically distinct from the alkanes, this class of hydrocarbons is referred to by some as the "cyclic alkanes." As their description implies, they contain one or more rings. |
Simple cycloalkanes have a prefix "cyclo-" to distinguish them from alkanes. Cycloalkanes are named as per their acyclic counterparts with respect to the number of carbon atoms in their backbones, e.g., cyclopentane (C5H10) is a cycloalkane with 5 carbon atoms just like pentane (C5H12), but they are joined up in a five... |
Substituted cycloalkanes are named similarly to substituted alkanes – the cycloalkane ring is stated, and the substituents are according to their position on the ring, with the numbering decided by the Cahn–Ingold–Prelog priority rules. |
Trivial/common names |
The trivial (non-systematic) name for alkanes is 'paraffins'. Together, alkanes are known as the 'paraffin series'. Trivial names for compounds are usually historical artifacts. They were coined before the development of systematic names, and have been retained due to familiar usage in industry. Cycloalkanes are also c... |
Branched-chain alkanes are called isoparaffins. "Paraffin" is a general term and often does not distinguish between pure compounds and mixtures of isomers, i.e., compounds of the same chemical formula, e.g., pentane and isopentane. |
In IUPAC |
The following trivial names are retained in the IUPAC system: |
isobutane for 2-methylpropane |
isopentane for 2-methylbutane |
neopentane for 2,2-dimethylpropane. |
Non-IUPAC |
Some non-IUPAC trivial names are occasionally used: |
cetane, for hexadecane |
cerane, for hexacosane |
Physical properties |
All alkanes are colorless. Alkanes with the lowest molecular weights are gasses, those of intermediate molecular weight are liquids, and the heaviest are waxy solids. |
Table of alkanes |
Boiling point |
Alkanes experience intermolecular van der Waals forces. Stronger intermolecular van der Waals forces give rise to greater boiling points of alkanes. |
There are two determinants for the strength of the van der Waals forces: |
the number of electrons surrounding the molecule, which increases with the alkane's molecular weight |
the surface area of the molecule |
Under standard conditions, from CH4 to C4H10 alkanes are gaseous; from C5H12 to C17H36 they are liquids; and after C18H38 they are solids. As the boiling point of alkanes is primarily determined by weight, it should not be a surprise that the boiling point has almost a linear relationship with the size (molecular weigh... |
A straight-chain alkane will have a boiling point higher than a branched-chain alkane due to the greater surface area in contact, thus the greater van der Waals forces, between adjacent molecules. For example, compare isobutane (2-methylpropane) and n-butane (butane), which boil at −12 and 0 °C, and 2,2-dimethylbutane ... |
On the other hand, cycloalkanes tend to have higher boiling points than their linear counterparts due to the locked conformations of the molecules, which give a plane of intermolecular contact. |
Melting points |
The melting points of the alkanes follow a similar trend to boiling points for the same reason as outlined above. That is, (all other things being equal) the larger the molecule the higher the melting point. There is one significant difference between boiling points and melting points. Solids have more rigid and fixed ... |
The melting points of branched-chain alkanes can be either higher or lower than those of the corresponding straight-chain alkanes, again depending on the ability of the alkane in question to pack well in the solid phase. |
Conductivity and solubility |
Alkanes do not conduct electricity in any way, nor are they substantially polarized by an electric field. For this reason, they do not form hydrogen bonds and are insoluble in polar solvents such as water. Since the hydrogen bonds between individual water molecules are aligned away from an alkane molecule, the coexiste... |
Their solubility in nonpolar solvents is relatively high, a property that is called lipophilicity. Alkanes are, for example, miscible in all proportions among themselves. |
The density of the alkanes usually increases with the number of carbon atoms but remains less than that of water. Hence, alkanes form the upper layer in an alkane–water mixture. |
Molecular geometry |
The molecular structure of the alkanes directly affects their physical and chemical characteristics. It is derived from the electron configuration of carbon, which has four valence electrons. The carbon atoms in alkanes are described as sp3 hybrids, that is to say that, to a good approximation, the valence electrons ar... |
Bond lengths and bond angles |
An alkane has only C–H and C–C single bonds. The former result from the overlap of an sp3 orbital of carbon with the 1s orbital of a hydrogen; the latter by the overlap of two sp3 orbitals on adjacent carbon atoms. The bond lengths amount to 1.09 × 10−10 m for a C–H bond and 1.54 × 10−10 m for a C–C bond. |
The spatial arrangement of the bonds is similar to that of the four sp3 orbitals—they are tetrahedrally arranged, with an angle of 109.47° between them. Structural formulae that represent the bonds as being at right angles to one another, while both common and useful, do not accurately depict the geometry. |
Conformation |
The structural formula and the bond angles are not usually sufficient to completely describe the geometry of a molecule. There is a further degree of freedom for each carbon–carbon bond: the torsion angle between the atoms or groups bound to the atoms at each end of the bond. The spatial arrangement described by the to... |
Ethane forms the simplest case for studying the conformation of alkanes, as there is only one C–C bond. If one looks down the axis of the C–C bond, one will see the so-called Newman projection. The hydrogen atoms on both the front and rear carbon atoms have an angle of 120° between them, resulting from the projection o... |
The two conformations differ in energy: the staggered conformation is 12.6 kJ/mol (3.0 kcal/mol) lower in energy (more stable) than the eclipsed conformation (the least stable). |
This difference in energy between the two conformations, known as the torsion energy, is low compared to the thermal energy of an ethane molecule at ambient temperature. There is constant rotation about the C–C bond. The time taken for an ethane molecule to pass from one staggered conformation to the next, equivalent t... |
The case of higher alkanes is more complex but based on similar principles, with the antiperiplanar conformation always being the most favored around each carbon–carbon bond. For this reason, alkanes are usually shown in a zigzag arrangement in diagrams or in models. The actual structure will always differ somewhat fro... |
Spectroscopic properties |
Virtually all organic compounds contain carbon–carbon, and carbon–hydrogen bonds, and so show some of the features of alkanes in their spectra. Alkanes are notable for having no other groups, and therefore for the absence of other characteristic spectroscopic features of a functional group like –OH, –CHO, –COOH etc. |
Infrared spectroscopy |
The carbon–hydrogen stretching mode gives a strong absorption between 2850 and 2960 cm−1, while the carbon–carbon stretching mode absorbs between 800 and 1300 cm−1. The carbon–hydrogen bending modes depend on the nature of the group: methyl groups show bands at 1450 cm−1 and 1375 cm−1, while methylene groups show bands... |
NMR spectroscopy |
The proton resonances of alkanes are usually found at δH = 0.5–1.5. The carbon-13 resonances depend on the number of hydrogen atoms attached to the carbon: δC = 8–30 (primary, methyl, –CH3), 15–55 (secondary, methylene, –CH2–), 20–60 (tertiary, methyne, C–H) and quaternary. The carbon-13 resonance of quaternary carbon ... |
Mass spectrometry |
Alkanes have a high ionization energy, and the molecular ion is usually weak. The fragmentation pattern can be difficult to interpret, but, in the case of branched chain alkanes, the carbon chain is preferentially cleaved at tertiary or quaternary carbons due to the relative stability of the resulting free radicals. Th... |
Chemical properties |
Alkanes are only weakly reactive with most chemical compounds. The acid dissociation constant (pKa) values of all alkanes are estimated to range from 50 to 70, depending on the extrapolation method, hence they are extremely weak acids that are practically inert to bases (see: carbon acids). They are also extremely weak... |
Free radicals, molecules with unpaired electrons, play a large role in most reactions of alkanes, such as cracking and reformation where long-chain alkanes are converted into shorter-chain alkanes and straight-chain alkanes into branched-chain isomers. Moreover, redox reactions of alkanes involving free radical interm... |
In highly branched alkanes, the bond angle may differ significantly from the optimal value (109.5°) to accommodate bulky groups. Such distortions introduce a tension in the molecule, known as steric hindrance or strain. Strain substantially increases reactivity. |
However, in general and perhaps surprisingly, when branching is not extensive enough to make highly disfavorable 1,2- and 1,3-alkyl–alkyl steric interactions (worth ~3.1 kcal/mol and ~3.7 kcal/mol in the case of the eclipsing conformations of butane and pentane, respectively) unavoidable, the branched alkanes are actua... |
Reactions with oxygen (combustion reaction) |
All alkanes react with oxygen in a combustion reaction, although they become increasingly difficult to ignite as the number of carbon atoms increases. The general equation for complete combustion is: |
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