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 The structure and naming-nomenclature of halogenoalkanes once known as 'haloalkanes' ('alkyl halides') Part 1

 GCE-AS-A2-IB ADVANCED LEVEL ORGANIC CHEMISTRY

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Examples of displayed formula, graphic formula, molecular formula, skeletal formula, structural formula

• The generic suffix name (..ane) is based on the longest carbon chain. 1 carbon, methane; 2 carbons, ethane; 3 carbons, propane; 4 carbons, butane. After these 4 preserved 'old trivial' names, the name is 'numerically' systematic eg 5 carbons, pentane; 6 hexane, 7 heptane etc.
• The halogenoalkane structures are based on replacing one or more hydrogen atoms in the alkane structure with a halogen atom X (X = F, Cl, Br or I).
• The positions of the substituent(s), denoted with a prefix eg halo… or alkyl… groups, are denoted by using the lowest possible numbers for the associated carbon atoms in the main chain.
• If there is more than one 'type' of substituent eg using the prefixes: bromo…, chloro…, methyl… etc., they are written out in alphabetical order irrespective of carbon atom number (note: di, tri are ignored in using this rule).
• The examples on this page are based on 1 to 3 carbon atoms
• Some 'old' and commercial names are quoted in () though their use should be avoided if possible [but many still used - just put one into GOGGLE!].
• A sub-CLASSIFICATION based on structural differences, which can have chemical consequences on e.g. rate of reaction or products formed in a reaction.
  • Halogenoalkanes are classified according to the atoms/groups attached to the carbon of the halogen atom X.
  • Primary halogenoalkanes have the structure R-CH₂-X, R = H, alkyl, aryl etc. i.e. apart from chloromethane they have one alkyl/aryl group attached to the C of the C-X group.
    • e.g. chloroethane CH₃CH₂Cl
  • Secondary halogenoalkanes have the structure R₂CH-X, R = alkyl or aryl etc. i.e. they have two alkyl/aryl groups attached to the C of the C-X group.
    • e.g. 2-bromobutane CH₃CHBrCH₂CH₃ 
  • Tertiary halogenoalkanes have the structure R₃C-X, R = alkyl or aryl etc. i.e. they have three alkyl/aryl groups attached to the C of the C-X group.
    • e.g. 2-iodo-2-methylpropane (CH₃)₃CI
• NOTE: Some 'old' and commercial names are quoted in () though their use should be avoided if possible.

Examples of non-cyclo C1-3 HALOGENOALKANES

1. The simplest halogenoalkane is exemplified by chloromethane (methyl chloride), whose formula and structured are shown in 4 styles. (a)molecular formula, (b) abbreviated structural formula,

(c), full structural formula, (d) '3D' representation of the structural formula.

4. difluoromethane (a hydrofluorocarbon or HFC, methylene difluoride)

7. chlorodifluoromethane, (HCFC-22 a hydrochlorofluorocarbon or HCFC)

15. (a), (b) , (c), 1-bromopropane (propyl bromide)

16. (a), (b), (c) , (d), 2-bromopropane (isopropyl bromide)

17.(a), (b), (c) , 2-chloropropane (isopropyl chloride)

18.(a), (b), (c), (d) , 1-iodopropane (propyl iodide)

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