HALOGENOALKANES Haloalkanes Structure and Naming homologous series nomenclature (1) isomers alkyl halides CFC CFCs HCFC HCFCs HFC HFCs chloroalkanes bromoalkanes chloroethanes bromoethanes chloropropanes bromopropanes molecules

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Doc Brown's Chemistry Revising Organic Chemistry

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

Examples of displayed formula of halogenoalkanes, graphic formula, molecular formula, skeletal formula, structural formula of this homologous series

(1)The homologous series of HALOGENOALKANES

of general formula C_nH_2n+1X (X = F, Cl, Br or I, n = 1, 2 or 3)

Examples of displayed formula of halogenoalkane molecules, graphic formula, molecular formula, skeletal formula, structural formula including isomers of halogenoalkane molecules and some of the further halogen substitution products including CFCs, HFCs and HCFCs

Revision notes for GCE Advanced Subsidiary Level AS Advanced Level A2 IB Revise AQA GCE Chemistry OCR GCE Chemistry Edexcel GCE Chemistry Salters Chemistry CIE Chemistry revising courses for pre-university students (equal to US grade 11 and grade 12 and Honours/honors level courses)

(2) more haloalkanes of C₄ * (3) more haloalkanes_>C₄_including cyclo..

Some 'old' and commercial names are quoted in () though their use should be avoided if possible.

organic chemical id tests * m/c test on naming halogenoalkanes * type in name test on halogenoalkanes

Intermolecular forces & boiling points of halogenoalkanes compared to other organic molecules

The shapes and bond angles of simple molecules - section on bond angles in organic molecules

_{A
brief guide to halogenoalkane nomenclature}

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.
AND some abbrevations:
- CFC = chloroflurocarbon (molecule consists of C, Cl, F atoms)
- HFC = hydrofluorocarbon (molecule consists of C, H, F atoms)
- HCFC = hydrochlorofluorocarbon (molecule consists of C, H, Cl, F atoms)

The shapes and bond angles of simple molecules - section on bond angles in organic molecules

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.

2. to 7. Are examples of multi-substituted halogenoalkanes based on methane …

2. (a) trichlorofluoromethane, (CFC-11, a chlorofluorocarbon or CFC),

(b), chlorotrifluoromethane (a CFC)

3. (a) dichlorodifluoromethane, (CFC-12),

(b), dichlorofluoromethane (a HCFC)

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

5. tribromomethane

6. tetrachloromethane, (carbon tetrachloride)

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

8. Bromoethane (ethyl bromide) exemplifies the simplest mono-substituted alkane with 2 carbon atoms.

(a) molecular formula, (b) abbreviated structural formula,

(c) more expanded structural formula, (d) full graphic structural formula,

(e) '3D' structural formula, (f) skeletal formula

9. to 14., show a series of multi-substituted halogenoethane molecules (with the possibility of positional isomerism with only 2 carbon atoms) ...

9. (a) , 1-chloro-1,1,2-trifluoroethane, (b) 2-chloro-1,1,1-trifluoromethane (a HCFC), (c) , 1-chloro-1,2-difluoroethane, (d) , 2-chloro-1,1-difluoroethane, (e) , 1-chloro-1,2,2-trifluoroethane

10. (a) , 1-chloro-1-fluoroethane, (b) , 1-chloro-2-fluoroethane, (c) , 1-chloro-1,1-difluoroethane, (d) , 1,1,2-trichloro-1,2,2-trifluoroethane (CFC-113)

11. 2,2-dichloro-1,1,1-trifluoroethane (HCFC-123)

12. (a) , 1,1-difluoroethane (HFC-152a), (b) , 1,2-difluoroethane

13. (a) , 1,1-dichloro-1-fluoroethane (HCFC-141b), (b) , 1,1-dichloro-2,2-difluoroethane

14.(a) 1,1,1-trifluoroethane, (b) , 1,1,2-trifluoroethane, (c) 1,1,1,2-tetrafluoroethane (HFC-134a), (d) , 1,1,2,2-tetrafluoroethane

with 3 carbon atoms you get positional isomerism with only 1 halogen atom (1- or 2- …)

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)

19. With 2 like halogen atoms there are four positional isomers

(a) , , , 1,1-dichloropropane

(b) , , , 1,2-dichloropropane

(c) , , , 1,3-dichloropropane

(d) , , , 2,2-dichloropropane

20. with 3 like halogen atoms there are 5 positional isomers

(a) , , , 1,1,1-trifluoropropane

(b) , , , 1,1,2-trifluoropropane

(c) , , , 1,1,3-trifluoropropane

(d) , , , 1,2,2-trifluoropropane

(e) , , , 1,2,3-trifluoropropane