(c) doc b(c) doc b

3.1 The molecular structure and nomenclature - naming of halogenoalkanes

Doc Brown's Chemistry  Revising Advanced A Level Organic Chemistry - Revision Notes PART 3 HALOGENOALKANES (haloalkanes, alkyl halides)

3.1 The molecular structure and naming-nomenclature of halogenoalkanes once known as 'haloalkanes' ('alkyl halides') - 3.1.1 The homologous series of HALOGENOALKANES

of general formula CnH2n+1X (X = F, Cl, Br or I, initially n = 1, 2 or 3)

How do we name haloalkanes? What is the molecular structure of halogenoalkanes? This page describes the molecular structure and how to name halogenoalkanes of the simplest monosubstituted halogenoalkanes and some polysubstituted haloalkanes of the C1, C2 and C3 carbon chains. Examples of displayed formula of halogenoalkane molecules (fluoro, chloro, bromo and iodo alkane derivatives), graphic formula, molecular formula, skeletal formula, structural formula of these homologous series, including isomers of halogenoalkane molecules and some of the further halogen substitution products including CFCs, HFCs and HCFCs. Some 'old' trivial and commercial names of the fluoroalkanes, chloroalkanes, bromoalkanes, and iodoalkanes are quoted in () though their use should be avoided if possible.



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).
    • Therefore, where X = halogen, the halogenoalkane functional group is C-X i.e. C-F,  C-Cl,  C-Br,  C-I
  • As usual, in naming halogenoalkanes, the IUPAC nomenclature rules apply: The positions of the substituent(s), on the longest possible carbon chain, are denoted with a prefix eg halo… or alkyl… groups, 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 initial 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 GOOGLE!].
  • Formulae and styles of molecular representation
    • Molecular formula examples
      • The molecular formula tells you the number of atoms of each element in the molecule, a sort of summary formula, but it tells you nothing about how the atoms are arranged and bonded in the molecule e.g.
      • (c) doc b 1-chlorobutane has the molecular formula C4H9Cl
      • (c) doc b has the molecular formula C4H7Br2Cl
    • Empirical formula examples
      • The simplest whole number ratio formula found from experimental analysis.
      • e.g. for chloroethane (derived from the parent alkane ethane and reacted with chlorine) CH3CH2Cl the empirical formula is C2H5Cl, the same as the molecular formula.
      • Because there is only one halogen atom in monosubstituted alkanes, the empirical formula is always the same as the molecular formula.
      • However, for some dihalo derivatives, the empirical formula is 'half' the molecular formula.
        • e.g. for 1,2-dibromoethane, BrCH2CH2Br, molecular formula C2H4Br2, CH2Br is the empirical formula.
    • Structural formula examples
      • (c) doc b is 1-chlorobutane, an unambiguous structure (see below)
    • Condensed/shortened/abbreviated structural formula examples
      • (c) doc b is also 1-chlorobutane, and also an unambiguous structure if you know how to read it! i.e. you know it is really (c) doc b !
    • Displayed formula examples
      • (c) doc b 2-bromopropane, (c) doc b 1,2-dibromo-1-chlorobutane
      • A displayed formula shows all the individual atoms and bonds in the molecule, but makes all the bond angles look like 90o, when, in this case, the C-C-C, H-C-C, H-C-H, H-C-Br bond angles etc. are all ~109o.
      • Note in the 2nd example the use of minimum numbers and the alphabetical order rule, where the 'bromo' takes precedence over the 'dibromo'.
    • Skeletal formula examples
      • Here you just use dashes to indicate C-C bonds and (usually) only show bonds to non-carbon atoms, in this case halogen atoms in halogenoalkanes. It should give an idea of the shape of the molecule e.g. the zig-zag pattern of the carbon chain.
      • (c) doc b is 1-chlorobutane, note that you must show the bond to the non-carbon atom chlorine.
      • On the left you have 3 dashes for the C-C-C-C chain and the 4th dash to the chlorine atom.
      • 3-chloro-1,2-difluoro-3-methylpentane ==> (c) doc b ==> (c) doc b is an extreme example! Does it check out in your head?
  • A sub-CLASSIFICATION based on structural differences, which can have chemical consequences e.g. on the 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, 1-bromopropane
      • C6H5CH2Cl is an example of an aryl (aromatic) substituent attached to the carbon of the C-X bond.
    • 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-iodobutane CH3CHICH2CH3 , (c) doc b 2-chloropropane
    • 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-chloro-2-methylpropane (CH3)3CI (c) doc b
  • NOTE: Some 'old' and commercial names are quoted in () though their use should be avoided if possible.
  • AND some abbreviations:
    • CFC = chlorofluorocarbon (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

    • Virtually all the bond angles for the molecules on this page are ~109o e.g. the H-C-H, H-C-Cl, H-C-Br, Cl-C-F etc. bond angles will be ~109o


3.1.1 Examples of non-cyclo C1-C3 HALOGENOALKANES

Names in bold are the preferred IUPAC name for the halogenoalkanes

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

(c)(c) doc b, full displayed structural formula, (d)(c) doc b '3D' representation of the structural formula. The H-C-H and H-C-Cl bond angles will be ~109o

 

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

Watch out for the alphabetical order rule for the prefixes - fluoro, chloro, bromo, iodo, but NOT necessarily in that order!

(c) doc b 2. (a) trichlorofluoromethane, (CFC-11, a chlorofluorocarbon or CFC). The Cl-C-Cl and F-C-Cl bond angles will be ~109o

(b)(c) doc b, chlorotrifluoromethane (a CFC)

 

3. (c) doc b (a) dichlorodifluoromethane, (CFC-12),

(b)(c) doc b, dichlorofluoromethane (a HCFC)

 

4. (c) doc bdifluoromethane (a hydrofluorocarbon or HFC, methylene difluoride)

5. (c) doc btribromomethane

6. (c) doc btetrachloromethane, (carbon tetrachloride)

7. (c) doc bchlorodifluoromethane, (HCFC-22 a hydrochlorofluorocarbon or HCFC)

 

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

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

(c)(c) doc b more expanded structural formula, (d)(c) doc b full displayed structural formula. The H-C-H and H-C-Br bond angles will be ~109o

Extra images of bromoethane: , the latter being the skeletal formula

(e)(c) doc b '3D' structural formula, (f)(c) doc b 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) (c) doc b, 1-chloro-1,1,2-trifluoroethane

(b) (c) doc b2-chloro-1,1,1-trifluoromethane (a HCFC)

(c) (c) doc b, 1-chloro-1,2-difluoroethane

(d) (c) doc b, 2-chloro-1,1-difluoroethane

(e) (c) doc b, 1-chloro-1,2,2-trifluoroethane

 

10. (a) (c) doc b, 1-chloro-1-fluoroethane

(b) (c) doc b, 1-chloro-2-fluoroethane

(c) (c) doc b, 1-chloro-1,1-difluoroethane

(d) (c) doc b, 1,1,2-trichloro-1,2,2-trifluoroethane (CFC-113)

 

11. (c) doc b2,2-dichloro-1,1,1-trifluoroethane (HCFC-123)

 

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

(b) (c) doc b, 1,2-difluoroethane

 

13. (a) (c) doc b, 1,1-dichloro-1-fluoroethane (HCFC-141b)

(b) (c) doc b, 1,1-dichloro-2,2-difluoroethane

 

14.(a)(c) doc b 1,1,1-trifluoroethane

(b) (c) doc b, 1,1,2-trifluoroethane

(c) (c) doc b1,1,1,2-tetrafluoroethane (HFC-134a)

(d) (c) doc b, 1,1,2,2-tetrafluoroethane

 

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

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

 

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

 

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

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

 

19. (c) doc bWith 2 like halogen atoms there are four positional isomers e.g. for dichloropropanes

(a)(c) doc b , (c) doc b, (c) doc b, 1,1-dichloropropane

(b)(c) doc b , (c) doc b, (c) doc b, 1,2-dichloropropane

(c)(c) doc b  , (c) doc b, (c) doc b, 1,3-dichloropropane

(d)(c) doc b  , (c) doc b, (c) doc b, 2,2-dichloropropane

 

20.(c) doc b  with 3 like halogen atoms there are 5 positional isomers

(a)(c) doc b , (c) doc b, (c) doc b, 1,1,1-trifluoropropane

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

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

(d)(c) doc b , (c) doc b, (c) doc b, 1,2,2-trifluoropropane

(e)(c) doc b , (c) doc b, (c) doc b, 1,2,3-trifluoropropane


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, WJEC GCE AS A2 Chemistry, CCEA/CEA GCE AS A2 Chemistry revising courses for pre-university students (equal to US grade 11 and grade 12 and AP Honours/honors level courses) formulae keywords: how to name naming nomenclature empirical molecular formula graphic formula displayed formula skeletal formula structural isomers isomerism  haloalkanes halogenoalkanes alkyl halides chloroalkanes bromoalkanes iodoalkanes fluoro alkanes CFC HFC HCFC CFCs HFCs HCFCs CH3Cl CCl3F CCl2F2 CH2F2 CHBr3 CCl4 CHClF2 C2H5Br CH3CH2Br CH3-CH2 -Br CH2FCClF2 CF3CH2Cl CHCl FCH2F CH2F2CH2Cl CHF2CHClF CH3CHClF CH2ClCH2F CH3CClF2 CCl2FCClF2 CF3CHCl2 CH3CHF2 CH3CCl2F CH3CF3 CH2FCHF2 CH2FCF3 CHF2CHF2 C3H7Br CH3CH2CH2Br CH3-CH2-CH2-Br CH3CHClCH3 C3H7I CH3CH2CH2Br CH3-CH2-CH2-Br CH3CHBRCH3 CH3CHClCH3 C3H7I CH3-CH2-CH2-I CH3CH2CH2I C3H6Cl2 C3H6F3

(c) doc b(c) doc bDoc Brown's Chemistry  Revising Advanced Level Organic Chemistry

Revision Notes PART 3 HALOGENOALKANES (haloalkanes, alkyl halides)

3.1 The molecular structure and naming-nomenclature of halogenoalkanes

3.1.2 More examples of HALOGENOALKANES (of four carbons i.e. C4 molecules)

This page describes the molecular structure and naming of C4 halogenoalkanes e.g. 1-bromobutane, 2-chloro-2-methylpropqane of four carbon atoms etc. Examples of displayed formula of halogenoalkane molecules (fluoro, chloro, bromo and iodo alkane derivatives), graphic formula, molecular formula, skeletal formula, structural formula. Some 'old' trivial and commercial names are quoted in () though their use should be avoided if possible.


1. The molecular formula (c) doc b, where X = halogen, allows 4 isomers, 2 based on butane and 2 based on 2-methylpropane.

(a) (c) doc b, (c) doc b, (c) doc b, (c) doc b, 1-chlorobutane (butyl chloride)

(b) (c) doc b, (c) doc b, (c) doc b, (c) doc b, 2-chlorobutane

(c) (c) doc b, (c) doc b, (c) doc b, (c) doc b, 1-chloro-2-methylpropane

(d) (c) doc b, (c) doc b, (c) doc b, (c) doc b, 2-chloro-2-methylpropane (tert- or t-butyl chloride)

Watch out for the use of brackets () in abbreviated structural formulae e.g. (CH3)3CCl

 

2. (c) doc bproduces 9 isomers when the two halogen atoms are the same, 6 based on butane and 3 based on 2-methylpropane.

(a) (c) doc b, (c) doc b, (c) doc b, 1,1-dichlorobutane

(b) (c) doc b, (c) doc b, (c) doc b, 1,2-dichlorobutane

(c) (c) doc b, (c) doc b, (c) doc b, 1,3-dichlorobutane

(d) (c) doc b, (c) doc b, (c) doc b, 1,4-dichlorobutane

(e) (c) doc b, (c) doc b, (c) doc b, 2,2-dichlorobutane

(f) (c) doc b, (c) doc b, (c) doc b, 2,3-dichlorobutane

(g) (c) doc b, (c) doc b, (c) doc b, 1,1-dichloro-2-methylpropane

(h) (c) doc b, (c) doc b, (c) doc b, 1,2-dichloro-2-methylpropane

(i) (c) doc b, (c) doc b, (c) doc b, 1,3-dichloro-2-methylpropane

3. There are 8 isomers of the formula (c) doc bbased on butane

(a) 1-bromo-1-chlorobutane, (c) doc b, (c) doc b

(b) 1-bromo-2-chlorobutane, (c) doc b, (c) doc b

(c) 1-bromo-3-chlorobutane, (c) doc b, (c) doc b

(d) 1-bromo-4-chlorobutane, (c) doc b, (c) doc b

(e) 2-bromo-1-chlorobutane, (c) doc b, (c) doc b

(f) 2-bromo-2-chlorobutane, (c) doc b, (c) doc b

(g) 2-bromo-3-chlorobutane, (c) doc b, (c) doc b

(h) 3-bromo-1-chlorobutane, (c) doc b, (c) doc b

 

4. Other bromo-chloro alkanes based on propane or butane involving bromo, chloro and methyl substituent include …

(a) 1,2-dibromo-1-chlorobutane, C4H7Br2Cl, (c) doc b, (c) doc b

(b) 1,2-dibromo-2-chlorobutane, (c) doc b, (c) doc b

(c) 1,2-dibromo-3-chlorobutane, (c) doc b, (c) doc b

(d) 1,2-dibromo-4-chlorobutane, (c) doc b, (c) doc b

(e) 1,3-dibromo-1-chlorobutane, (c) doc b, (c) doc b

(f) 1,3-dibromo-2-chlorobutane, (c) doc b, (c) doc b

(g) 1,3-dibromo-3-chlorobutane, (c) doc b, (c) doc b

(h) 1,3-dibromo-4-chlorobutane, (c) doc b, (c) doc b

(i) 1,4-dibromo-1-chlorobutane,, (c) doc b . (c) doc b 1-bromo-1,4-dichlorobutane

(j) 1-bromo-1,2-dichlorobutane, C4H7BrCl2, (c) doc b, (c) doc b

(k) 1-bromo-1-chloro-2-methylpropane, C4H8BrCl, (c) doc b, (c) doc b

(l) 1-bromo-2-chloro-2-methylpropane, (c) doc b, (c) doc b

(m) 1-bromo-3-chloro-2-methylpropane, (c) doc b, (c) doc b

(n) 2-bromo-1-chloro-2-methylpropane, (c) doc b, (c) doc b

(o) 2-bromo-1,2-dichlorobutane, C4H7BrCl2, (c) doc b, (c) doc b

(p) 2-bromo-1,3-dichlorobutane, (c) doc b, (c) doc b

(q) 2-bromo-1,4-dichlorobutane, (c) doc b, (c) doc b

(r) 2-bromo-2,3-dichlorobutane, (c) doc b, (c) doc b

(s) 3-bromo-2,2-dichlorobutane, (c) doc b, (c) doc b


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, WJEC GCE AS A2 Chemistry, CCEA/CEA GCE AS A2 Chemistry revising courses for pre-university students (equal to US grade 11 and grade 12 and AP Honours/honors level courses) Formulae keywords: how to name naming nomenclature empirical molecular formula graphic formula displayed formula skeletal formula structural isomers isomerism C4H9Cl CH3CH2CH2CH2Cl C4H8Cl2 C4H8BrCl C4H7Br2Cl C4H7BrCl2 C4H8BrCl

(c) doc b(c) doc bDoc Brown's Chemistry  Revising Advanced Level Organic Chemistry

Revision Notes PART 3 HALOGENOALKANES (haloalkanes, alkyl halides)

3.1 Molecular structure and naming-nomenclature of halogenoalkanes

3.1.3a Examples of cyclohalogenoalkanes (sec. cyclohaloalkanes)

and 3.1.3b Open chain halogenoalkanes with 5 or more carbon atoms

This page describes the molecular structure and how to name secondary cyclohalogenoalkanes (cyclohaloalkanes) and then more halogenoalkanes of five carbon atoms (C5 haloalkane molecules - fluoro, chloro, bromo and iodo alkane derivatives). Examples of displayed formula of halogenoalkane molecules, graphic formula, molecular formula, skeletal formula, structural formula. Some 'old' trivial and commercial names are quoted in () though their use should be avoided if possible.


3.1.3a Examples of cyclohalogenoalkanes (sec. cyclohaloalkanes)

  1. C3H5Cl, (c) doc b , chlorocyclopropane
  2. C3H5F, (c) doc b , (c) doc b , fluorocyclopropane
  3. C3H4Cl2, (c) doc b 1,1-dichlorocyclopropane
  4. C3H4Cl2,(c) doc b 1,2-dichlorocyclopropane
  5. C4H7Br,(c) doc b, (c) doc b,  bromocyclobutane
  6. C4H6Br2,(c) doc b 1,1-dibromocyclobutane
  7. C4H6Br2,(c) doc b  1,2-dibromocyclobutane
  8. C4H6Br2,(c) doc b 1,3-dibromocyclobutane
  9. C5H9I,(c) doc b  iodocyclopentane
  10. C5H8Br2,(c) doc b 1,1-dibromocyclopentane
  11. C5H8Br2,(c) doc b, (c) doc b,  1,2-dibromocyclopentane
  12. C5H8Br2,(c) doc b  1,3-dibromocyclopentane
  13. C6H11Cl,(c) doc b  chlorocyclohexane
  14. C6H11Br,(c) doc b  bromocyclohexane
  15. C6H11F,(c) doc b fluorocyclohexane
  16. C6H11I,(c) doc b  iodocyclohexane
  17. C6H10Br2,(c) doc b , (c) doc b, 1,1-dibromocyclohexane
  18. C6H10Br2,(c) doc b 1,2-dibromocyclohexane
  19. C6H10Br2,(c) doc b  1,3-dibromocyclohexane
  20. C6H10Br2,(c) doc b  1,4-dibromocyclohexane
  21. C6H9Cl3,(c) doc b 1,1,2-trichlorocyclohexane
  22. C6H9Cl3,(c) doc b 1,1,3-trichlorocyclohexane
  23. C6H9Cl3,(c) doc b, (c) doc b, 1,1,4-trichlorocyclohexane
  24. C6H9Cl3,(c) doc b  1,2,3-trichlorocyclohexane
  25. C6H9Cl3,(c) doc b 1,2,4-trichlorocyclohexane

3.1.3b Open chain halogenoalkanes with 5 or more carbon atoms

  1. 1-chloro-2,2-dimethylpropane, C5H11Cl, (c) doc b, (c) doc b, (c) doc b

    Watch out for the use of brackets () in abbreviated structural formulae e.g. (CH3)3CCH2Cl

  2. 1-chloro-2-methylbutane, C5H11Cl, (c) doc b, (c) doc b, (c) doc b
  3. Again watch out for the use of brackets () in abbreviated structural formulae e.g. the (CH3) on the 3rd carbon.

  4. 1-chloro-4-fluoro-2-methylbutane, C5H1OClF, (c) doc b, (c) doc b
  5. 1-chloro-3-methylbutane, C5H11Cl, (c) doc b, (c) doc b, (c) doc b
  6. 1-chloro-2-fluoro-3-methylbutane, C5H1OClF, (c) doc b, (c) doc b
  7. 2-chloro-2-methylbutane, C5H11Cl, (c) doc b, (c) doc b, (c) doc b
  8. 3-bromo-2-chloro-2-methylbutane, C5H10BrCl, (c) doc b, (c) doc b
  9. 2-chloro-3-methylbutane, C5H11Cl, (c) doc b, (c) doc b, (c) doc b
  10. 1,2-dichloro-3-methylbutane, C5H10Cl2, (c) doc b, (c) doc b
  11. 1-chloro-2,2-dimethylbutane, C5H10Cl2, (c) doc b, (c) doc b, (c) doc b
  12. 1-chloro-3-iodo-2,2-dimethylbutane, C6H12ICl, (c) doc b, (c) doc b
  13. 1-chloro-2,3-dimethylbutane, C6H13Cl, (c) doc b, (c) doc b, (c) doc b
  14. 1-chloro-2-fluoro-2,3-dimethylbutane, C6H12ClF, (c) doc b, (c) doc b
  15. 1-chloro-3,3-dimethybutane, C6H13Cl, (c) doc b, (c) doc b, (c) doc b
  16. 1-bromo-4-chloro-2,2-dimethylbutane, C6H12ClBr, (c) doc b, (c) doc b
  17. 3-chloro-2,2-dimethylbutane, C6H13Cl, (c) doc b, (c) doc b, (c) doc b
  18. 2-chloro-1-iodo-3,3-dimethylbutane, C6H12ClI, (c) doc b, (c) doc b
  19. 1-chloropentane (n-pentyl chloride), C5H11Cl, (c) doc b, (c) doc b, (c) doc b
  20. 1,3-dichloropentane, C5H10Cl2, (c) doc b, (c) doc b
  21. 2-chloropentane, C5H11Cl, (c) doc b, (c) doc b, (c) doc b
  22. 4-chloro-1-fluoropentane, C5H10ClF, (c) doc b, (c) doc b
  23. 3-chloropentane, C5H11Cl, (c) doc b, (c) doc b, (c) doc b
  24. 3-chloro-2-fluoropentane, C5H10ClF, (c) doc b, (c) doc b
  25. 1-chloro-2-methylpentane, C6H13Cl, (c) doc b, (c) doc b, (c) doc b
  26. 1-chloro-4-iodo-2-methylpentane, C6H12ClI, (c) doc b, (c) doc b
  27. 1-chloro-3-methylpentane, C6H13Cl, (c) doc b, (c) doc b, (c) doc b
  28. 1-chloro-3-ethylpentane, C7H15Cl, (c) doc b, (c) doc b
  29. 4-bromo-1-chloro-3-methylpentane, C6H12ClBr, (c) doc b, (c) doc b
  30. 1-chloro-4-methylpentane, C6H13Cl(c) doc b, (c) doc b, (c) doc b
  31. 1-chloro-2-iodo-4-methylpentane, C6H12lCl, (c) doc b, (c) doc b
  32. 2-chloro-2-methylpentane, C6H13Cl, (c) doc b, (c) doc b, (c) doc b
  33. 2-chloro-4-fluoro-2-methylpentane, C6H12ClF, (c) doc b, (c) doc b
  34. 2-chloro-3-methylpentane, C6H13Cl, (c) doc b, (c) doc b, (c) doc b
  35. 2-chloro-3-ethylpentane, C7H15Cl, (c) doc b, (c) doc b
  36. 1-bromo-4-chloro-3-methylpentane, C6H12BrCl, (c) doc b, (c) doc b
  37. 2-chloro-4-methylpentane, C6H13Cl, (c) doc b, (c) doc b, (c) doc b
  38. 2-chloro-3-fluoro-4-methylpentaneC6H12ClF, (c) doc b, (c) doc b
  39. 3-chloro-2-methylpentane, C6H13Cl, (c) doc b, (c) doc b, (c) doc b
  40. 2,3-dichloro-4-methylpentane, C6H12Cl2, (c) doc b, (c) doc b
  41. 3-chloro-3-methylpentane, C6H13Cl, (c) doc b, (c) doc b, (c) doc b
  42. 3-chloro-3-ethylpentane, C7H15Cl, (c) doc b, (c) doc b
  43. 3-chloro-1,2-difluoro-3-methylpentane, C6H11ClF2, (c) doc b, (c) doc b
  44. 1-chlorohexane (n-hexyl chloride), C6H13Cl, (c) doc b, (c) doc b, (c) doc b
  45. 1-chloro-3-ethylhexane, C8H17Cl, (c) doc b, (c) doc b
  46. 1-chloro-4-ethylhexane, C8H17Cl, (c) doc b, (c) doc b
  47. 1,1-dichlorohexane, C6H12Cl2, (c) doc b
  48. 1,2-dichlorohexane, C6H12Cl2, (c) doc b
  49. 1,3-dichlorohexane, C6H12Cl2, (c) doc b
  50. 1,4-dichlorohexane, C6H12Cl2, (c) doc b, (c) doc b
  51. 1,5-dichlorohexane, C6H12Cl2, (c) doc b
  52. 1,6-dichlorohexane, C6H12Cl2, (c) doc b
  53. 2-chlorohexane, C6H13Cl, (c) doc b, (c) doc b, (c) doc b
  54. 2-chloro-3-ethylhexane, C8H17Cl, (c) doc b, (c) doc b
  55. 2-chloro-4-ethylhexane, C8H17Cl, (c) doc b, (c) doc b
  56. 2,2-dichlorohexane, C6H12Cl2, (c) doc b
  57. 2,3-dichlorohexane, C6H12Cl2, (c) doc b, (c) doc b
  58. 2,4-dichlorohexane, C6H12Cl2, (c) doc b, (c) doc b
  59. 2,5-dichlorohexane, C6H12Cl2, (c) doc b
  60. 3-chlorohexane, C6H13Cl, (c) doc b, (c) doc b, (c) doc b
  61. 3-chloro-3-ethylhexane, C8H17Cl, (c) doc b, (c) doc b
  62. 3-chloro-4-ethylhexane, C8H17Cl, (c) doc b, (c) doc b
  63. 3,3-dichlorohexane, C8H16Cl2, (c) doc b
  64. 3,4-dichlorohexane, C8H16Cl2, (c) doc b


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, WJEC GCE AS A2 Chemistry, CCEA/CEA GCE AS A2 Chemistry revising courses for pre-university students (equal to US grade 11 and grade 12 and AP Honours/honors level courses) Formulae keywords: how to name naming nomenclature empirical molecular formula graphic formula displayed formula skeletal formula structural isomers isomerism halogen compounds C3H5F C3H5Cl C3H4Cl2 C4H7Br C4H6Br2 C5H9I C5H8Br2 C6H11Cl C6H11F C6H11I C6H10Br2 C6H9Cl3 C5H11Cl C5H1OClF C5H10BrCl C5H10ClBr C5H10Cl2 C6H12ICl C6H13Cl C6H12ClF C6H13Cl C6H12ClBr C6H12ClI C5H11Cl C5H10Cl2 C5H11Cl C5H10ClF C6H13Cl C6H12ClI C7H15Cl C6H12ClBr C7H15Cl C8H17Cl C6H12Cl2 C8H16Cl2 C6H12lCl C6H12ClF C6H12BrCl C6H12ClF C6H12Cl2 C6H11ClF2 These detailed notes on the structure and naming of halogenoalkanes include the general formula of halogenoalkane molecules, empirical formula of halogenoalkane molecules, structural formula of halogenoalkane molecules, skeletal formula of halogenoalkane molecules, displayed formula of halogenoalkane molecules, shapes of halogenoalkane molecules, isomers of halogenoalkane molecules IUPAC rules for halogenoalkane nomenclature. Students should be able to draw structural formula of halogenoalkane, displayed and skeletal formulas for halogenoalkane organic compounds apply IUPAC rules for nomenclature to name halogenoalkane acid organic compounds including chains and rings and be able to apply IUPAC rules for nomenclature to draw the structural, displayed or skeletal structure of halogenoalkane organic compounds from the halogenoalkane IUPAC name from the homologous series of halogenoalkanes

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