Part 1
Naming halogenoalkanes.
Remember the rules we learnt when naming alkanes, these rules are on top of those.
As usual, in naming halogenoalkanes, the IUPAC nomenclature rules apply:
The prefix for each halogenoalkane name becomes: fluoro..., chloro..., bromo..., iodo...
bromoethane, 1-iodopropane
You use the lowest possible numbers for the associated carbon atoms in the main chain.
2-chlorobutane, NOT 3-chlorobutane (doesn't matter which end you start counting from)
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).
1,2-dibromo-1-chlorobutane, but you still use the lowest numbers possible on the carbon chain i.e.
you would not name the above 3,4-dibromo-4-chlorobutane.
You will meet many more as we go through the work.
Classifying halogenoalkanes
A halogenoalkane can be classed as primary 1 o, secondary 2o, or tertiary 3o. These can have
significant chemical consequences e.g. on the rate of the reaction, mechanism of the reaction or the
products formed in the reaction.
Halogenoalkanes are classified according to the atoms/groups attached to the carbon of the halogen
atom X.
Look at the carbon atom bonded to the halogen atom, then count the number of carbon atoms
bonded to it.
1-bromopropane
There is one carbon atom bonded to the carbon circled in red, so this is a 1 o (primary)
halogenoalkane.
2-chloropropane
There are two carbon atoms bonded to the carbon circled in red, so this is a 2 o (secondary)
halogenoalkane.
2-chloro-2-methylpropane (CH3)3CI
There are three carbon atoms bonded to the carbon circled in red, so this is a 3 o (tertiary)
halogenoalkane.
Part2
Structures of halogenoalkanes
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 which the full displayed formula of these halogenoalkanes does e.g.
1-chlorobutane has the molecular formula C4H9Cl
1,3-dibromo-3-chlorobutane has the molecular formula C4H7Br2Cl
Empirical formula examples of halogenoalkanes
The simplest whole number ratio formula found from experimental analysis.
e.g. for chloroethane (derived from the parent alkane ethane and reacted with chlorine) CH 3CH2Cl
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 of halogenoalkanes
is 1-chlorobutane
is also 1-chlorobutane
!
Displayed formula examples
2-bromopropane,
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
109.5o
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 of halogenoalkanes
Carbon and hydrogen atoms are not usually shown in skeletal formula.
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 e.g. -F, -Cl, -Br or -I.
It should give an idea of the shape of the molecule e.g. the zig-zag pattern of the carbon chain.
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
