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the (381), and (204), alkanes (154), are (111), chemistry (75), for (74), #carbon (68), with (55), edit (50), from (47), methane (46), alkane (43), chain (42), which (34), atoms (33), hydrogen (32), chemical (32), they (32), isomers (31), this (29), hydrocarbons (29), other (29), have (27), that (27), their (26), can (26), organic (25), branched (25), molecular (24), more (23), solid (23), not (23), doi (22), number (22), also (20), acid (20), butane (20), ethane (20), group (19), bonds (19), one (18), gas (18), than (18), compounds (17), reactions (17), only (17), higher (17), liquid (17), melting (17), retrieved (16), pentane (16), iupac (16), name (16), cycloalkanes (15), octane (15), points (15), linear (14), structure (14), two (14), point (14), example (14), form (14), such (14), bond (13), propane (13), isbn (13), pmid (13), some (13), its (13), water (13), between (13), has (13), nomenclature (12), molecules (12), free (12), oil (12), straight (12), using (11), use (11), all 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ane c 30 4 111 846 763 isomers of triacontane c 40 62 481 801 147 341 isomers of tetracontane c 50 1 117 743 651 746 953 270 isomers of pentacontane c 60 22 158 734 535 770 411 074 184 isomers of hexacontane branched alkanes can be chiral for example 3 methylhexane and its higher homologues are chiral due to their stereogenic center at carbon atom number 3 the above list only includes differences of connectivity not stereochemistry in addition to the alkane isomers the chain of carbon atoms may form one or more rings such compounds are called cycloalkanes and are also excluded from the above list because changing the number of rings changes the molecular formula for example cyclobutane and methylcyclopropane are isomers of each other c 4 h 8 but are not isomers of butane c 4 h 10 branched alkanes are more thermodynamically stable than their linear or less branched isomers for example the highly branched 2 2 3 3 tetramethylbutane is about 1 9 kcal mol more stable than its linear isomer n octane 5 nomenclature edit main article iupac nomenclature of organic chemistry the iupac nomenclature systematic way of naming compounds for alkanes is based on identifying hydrocarbon chains unbranched saturated hydrocarbon chains are named systematically with a greek numerical prefix denoting the number of carbons and the suffix ane 6 in 1866 august wilhelm von hofmann suggested systematizing nomenclature by using the whole sequence of vowels a e i o and u to create suffixes ane ene ine or yne one une for the hydrocarbons c n h 2 n 2 c n h 2 n c n h 2 n 2 c n h 2 n 4 c n h 2 n 6 7 in modern nomenclature the first three specifically name hydrocarbons with single double and triple bonds 8 while one now represents a ketone linear alkanes edit further information list of straight chain alkanes straight chain alkanes are sometimes indicated by the prefix n for normal where a non linear isomer exists although this is not strictly necessary and is not part of the iupac naming system the usage is still common in cases where one wishes to emphasize or distinguish between the straight chain and branched chain isomers e g n butane rather than simply butane to differentiate it from isobutane alternative names for this group used in the petroleum industry are linear paraffins or n paraffins the first eight members of the series in terms of number of carbon atoms are named as follows methane ch 4 one carbon and 4 hydrogen ethane c 2 h 6 two carbon and 6 hydrogen propane c 3 h 8 three carbon and 8 hydrogen butane c 4 h 10 four carbon and 10 hydrogen pentane c 5 h 12 five carbon and 12 hydrogen hexane c 6 h 14 six carbon and 14 hydrogen heptane c 7 h 16 seven carbons and 16 hydrogen octane c 8 h 18 eight carbons and 18 hydrogen the first four names were derived from methanol ether propionic acid and butyric acid alkanes with five or more carbon atoms are named by adding the suffix ane to the appropriate numerical multiplier prefix 9 with elision of any terminal vowel a or o from the basic numerical term hence pentane c 5 h 12 hexane c 6 h 14 heptane c 7 h 16 octane c 8 h 18 etc the numeral prefix is generally greek however alkanes with a carbon atom count ending in nine for example nonane use the latin prefix non branched alkanes edit ball and stick model of isopentane common name or 2 methylbutane iupac systematic name simple branched alkanes often have a common name using a prefix to distinguish them from linear alkanes for example n butane isobutane or i butane for the two isomers of butane and n pentane isopentane neopentane for the three isomers of pentane iupac naming conventions can be used to produce a systematic name the key steps in the naming of more complicated branched alkanes are as follows 10 identify the longest continuous chain of carbon atoms name this longest root chain using standard naming rules name each side chain by changing the suffix of the name of the alkane from ane to yl number the longest continuous chain in order to give the lowest possible numbers for the side chains 11 number and name the side chains before the name of the root chain if there are multiple side chains of the same type use prefixes such as di and tri to indicate it as such and number each one add side chain names in alphabetical disregarding di etc prefixes order in front of the name of the root chain comparison of nomenclatures for three isomers of c 5 h 12 common name n pentane isopentane neopentane iupac name pentane 2 methylbutane 2 2 dimethylpropane structure saturated cyclic hydrocarbons edit main article cycloalkane 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 c 5 h 10 is a cycloalkane with 5 carbon atoms just like pentane c 5 h 12 but they are joined up in a five membered ring in a similar manner propane and cyclopropane butane and cyclobutane etc 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 9 trivial common names edit main article list of straight chain alkanes 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 called naphthenes 12 13 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 14 physical properties edit see also higher alkane and list of straight chain alkanes all alkanes are colorless 15 16 alkanes with the lowest molecular weights are gases those of intermediate molecular weight are liquids and the heaviest are waxy solids 17 18 table of alkanes edit alkane formula boiling point note 1 c melting point note 1 c density note 1 kg m 3 at 20 c isomers note 2 methane ch 4 162 182 0 656 gas 1 ethane c 2 h 6 89 183 1 26 gas 1 propane c 3 h 8 42 188 2 01 gas 1 butane c 4 h 10 0 138 2 48 gas 2 pentane c 5 h 12 36 130 626 liquid 3 hexane c 6 h 14 69 95 659 liquid 5 heptane c 7 h 16 98 91 684 liquid 9 octane c 8 h 18 126 57 703 liquid 18 nonane c 9 h 20 151 54 718 liquid 35 decane c 10 h 22 174 30 730 liquid 75 undecane c 11 h 24 196 26 740 liquid 159 dodecane c 12 h 26 216 10 749 liquid 355 tridecane c 13 h 28 235 5 4 756 liquid 802 tetradecane c 14 h 30 253 5 9 763 liquid 1858 pentadecane c 15 h 32 270 10 769 liquid 4347 hexadecane c 16 h 34 287 18 773 liquid 10 359 heptadecane c 17 h 36 303 22 777 solid 24 894 octadecane c 18 h 38 317 28 781 solid 60 523 nonadecane c 19 h 40 330 32 785 solid 148 284 eicosane c 20 h 42 343 37 789 solid 366 319 triacontane c 30 h 62 450 66 810 solid 4 111 846 763 tetracontane c 40 h 82 525 82 817 solid 62 481 801 147 341 pentacontane c 50 h 102 575 91 824 solid 1 1 10 18 hexacontane c 60 h 122 625 100 829 solid 2 2 10 22 heptacontane c 70 h 142 solid 4 7 10 26 octacontane c 80 h 162 solid 1 1 10 31 nonacontane c 90 h 182 solid 2 5 10 35 hectane c 100 h 202 solid 5 9 10 39 1 2 3 physical properties of the straight chain isomer total number of constitutional isomers for this molecular formula boiling points edit melting blue and boiling orange points of the first 16 n alkanes in c alkanes experiences intermolecular van der waals forces the cumulative effects of these intermolecular forces give rise to greater boiling points of alkanes 19 two factors influence 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 ch 4 to c 4 h 10 alkanes are gaseous from c 5 h 12 to c 17 h 36 they are liquids and after c 18 h 38 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 an almost linear relationship with the size molecular weight of the molecule as a rule of thumb the boiling point rises 20 30 c for each carbon added to the chain this rule applies to other homologous series 19 a straight chain alkane will have a boiling point higher than a branched chain alkane due to the greater surface area in contact and thus greater van der waals forces between adjacent molecules for example compare isobutane 2 methylpropane and n butane which boil at 12 and 0 c and 2 2 dimethylbutane and 2 3 dimethylbutane which boil at 50 and 58 c respectively 19 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 edit 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 however alkanes melting points follow a more complex pattern due to variations in the properties of their solid crystals a one difference in crystal structure that even numbered alkanes from hexane onwards tend to form denser packed crystals compared to their odd numbered neighbors this causes them to have a greater enthalpy of fusion amount of energy required to melt them raising their melting point 20 a second difference in crystal structure is that even numbered alkanes from octane onwards tend to form more rotationally ordered crystals compared to their odd numbered neighbors this causes them to have a greater entropy of fusion increase in disorder from the solid to the liquid state lowering their melting point 21 while these effects operate in opposing directions the first effect tends to be slightly stronger leading even numbered alkanes to have slightly higher melting points than the average of their odd numbered neighbors this trend does not apply to methane which has an unusually high melting point higher than both ethane and propane this is because it has a very low entropy of fusion attributable to its high molecular symmetry and the rotational disorder in solid methane near its melting point methane i 21 the melting points of branched chain alkanes can be either higher or lower than those of the corresponding straight chain alkanes again depending on these two factors more symmetric alkanes tend towards higher melting points due to enthalpic effects when they form ordered crystals and entropic effects when they form disordered crystals e g neopentane 21 conductivity and solubility edit 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 coexistence of an alkane and water leads to an increase in molecular order a reduction in entropy as there is no significant bonding between water molecules and alkane molecules the second law of thermodynamics suggests that this reduction in entropy should be minimized by minimizing the contact between alkane and water alkanes are said to be hydrophobic as they are insoluble in water 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 22 molecular geometry edit sp 3 hybridization in methane 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 sp 3 hybrids that is to say that to a good approximation the valence electrons are in orbitals directed towards the corners of a tetrahedron which are derived from the combination of the 2s orbital and the three 2p orbitals geometrically the angle between the bonds are cos 1 1 3 109 47 this is exact for the case of methane while larger alkanes containing a combination of c h and c c bonds generally have bonds that are within several degrees of this idealized value bond lengths and bond angles edit the tetrahedral structure of methane an alkane has only c h and c c single bonds the former result from the overlap of an sp 3 orbital of carbon with the 1s orbital of a hydrogen the latter by the overlap of two sp 3 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 sp 3 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 edit main article alkane stereochemistry newman projections of two of many conformations of ethane eclipsed on the left staggered on the right ball and stick models of the two rotamers of ethane the spatial arrangement of the c c and c h bonds are described by the torsion angles of the molecule known as its conformation in ethane the simplest case for studying the conformation of alkanes there is nearly free rotation about a carbon carbon single bond two limiting conformations are important eclipsed conformation and staggered conformation the staggered conformation is 12 6 kj mol 3 0 kcal mol lower in energy more stable than the eclipsed conformation the least stable in highly branched alkanes the bond angle may differ 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 23 spectroscopic properties edit spectroscopic signatures for alkanes are obtainable by the major characterization techniques 24 infrared spectroscopy edit the c h stretching mode gives strong absorptions between 2850 and 2960 cm 1 and weaker bands for the c c stretching mode absorbs between 800 and 1300 cm 1 the ...