☰ Contents · Chemistry (Organic chemistry)

Alkanes: general formula, homologous series, rational nomenclature

Lessons 5 · 1 lessons · A. Mutalibov, E. Murodov, S. Masharipov, H. Islomova. Organic Chemistry, Grade 10, 1st edition. G‘afur G‘ulom Publishing House, Tashkent, 2017
5

General formula and homologous series of alkanes. Rational nomenclature

Textbook: pp. 21–25
GoalDescribe the general formula and homologous series of alkanes and write radicals and rational-nomenclature names.
New words
alkanes · alkanlarhomologous series · gomologik qatoralkyl radical · alkil radikalrational nomenclature · ratsional nomenklatura
Explanation

Alkanes are open-chain saturated hydrocarbons whose carbon atoms are joined only by σ-bonds; the general formula is CₙH₂ₙ₊₂. The first members are methane CH₄, ethane C₂H₆, propane C₃H₈, butane C₄H₁₀; from pentane on the name is a numeral for the number of carbons (mostly Greek: penta-, hexa-, hepta-, octa-, deca-; nona- is Latin) plus “-ane”. Substances with similar structure and close properties whose compositions differ by a –CH₂– group are homologues, and their set is a homologous series. Removing one hydrogen atom from an alkane gives a radical of formula CₙH₂ₙ₊₁–, named by changing “-ane” to “-yl”: methyl CH₃–, ethyl C₂H₅–, propyl C₃H₇–, isopropyl (CH₃)₂CH–, isobutyl (CH₃)₂CH–CH₂–. Compounds are named in three nomenclatures: trivial (historical), rational and systematic. In rational nomenclature an alkane is regarded as a derivative of methane: the most branched carbon is the “methane centre”, the radicals attached to it are listed from the simplest to the most complex, and the name ends in “methane”: (CH₃)₂CH₂ is dimethylmethane (propane), (C₂H₅)₂CH₂ is diethylmethane (pentane).

Worked examples
In CH₃–CH₂–CH(CH₃)–CH₃ (2-methylbutane) the most branched carbon carries two CH₃ and one C₂H₅: rational name dimethylethylmethane. HC(CH₃)₃ is trimethylmethane, i.e. isobutane.
An alkane with M = 72: 14n + 2 = 72, so n = 5 and the compound is C₅H₁₂ (pentane). In ethane the mass fraction of carbon is 24/30 = 80 %.
Class activity

Alkane card game: write formulas from methane to decane on 10 sheets, shuffle them, and let a partner sort them in order; say that neighbouring cards differ by –CH₂–.

Practice
1
Write the general formula of alkanes.
2
Find the total number of covalent bonds (C–C and C–H) in nonane C₉H₂₀.
3
What percent of ethane by mass is carbon (C = 12, H = 1)?
4
Why are methane and ethane homologues while ethane and ethylene are not?