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REACTIONS OF
HALOGENOALKANES
© www.chemsheets.co.uk AS 1140 2-Feb-2016
R X + NaOH R OH + NaX
: OH-
C X
Nucleophilic
substitution
© www.chemsheets.co.uk AS 1140 2-Feb-2016
.g. bromoethane + aqueous NaOH
R X + NaOH R OH + NaX
C H3 C H2 Br + NaOH C H3 C H2 OH + NaBr
: OH-
: OH-
C X C H3 C H2 Br
Nucleophilic
substitution
© www.chemsheets.co.uk AS 1140 2-Feb-2016
.g. 2-chloropropane + aqueous NaOH
R X + NaOH R OH + NaX
C H3 C H C H 3 + NaOH C H3 C H C H3 + NaCl
Cl OH
: OH-
: OH-
C X C H3 CH C H3
Cl Nucleophilic
substitution
© www.chemsheets.co.uk AS 1140 2-Feb-2016
.g. 1-bromopropane + aqueous NaOH
R X + NaOH R OH + NaX
C H3 C H2 C H2 Br + NaOH C H3 C H2 C H2 OH + NaBr
: OH- : OH-
C X C H3 C H2 C H2 Br
Nucleophilic
substitution
© www.chemsheets.co.uk AS 1140 2-Feb-2016
g. 2-iodo-3-methylbutane + aqueous NaOH
R X + NaOH R OH + NaX
C H3 C H3
C H3 CH CH C H 3 + NaOH C H3 CH CH C H3 + NaI
I OH
: OH- : OH-
C H3
C X
C H3 C H CH C H3
I Nucleophilic
substitution
© www.chemsheets.co.uk AS 1140 2-Feb-2016
R X + KCN R CN + KX
: CN-
C X
Nucleophilic
substitution
© www.chemsheets.co.uk AS 1140 2-Feb-2016
.g. 2-chloropropane + ethanolic KCN
R X + KCN R CN + KX
C H3 C H C H 3 + KCN C H3 C H C H3 + KCl
Cl CN
: CN-
: CN-
C X
C H3 CH C H3
Cl Nucleophilic
substitution
© www.chemsheets.co.uk AS 1140 2-Feb-2016
.g. 1-bromobutane + ethanolic KCN
R X + KCN R CN + KX
C H3 C H2 C H2 C H2 Br + KCN
C H 3 C H 2 C H 2 C H 2 CN + KBr
: CN-
: CN-
C X C H3 C H2 C H2 C H2 Br
Nucleophilic
substitution
© www.chemsheets.co.uk AS 1140 2-Feb-2016
R X + 2 NH3 R N H 2 + NH 4X
: NH3 H
C X C N+ H
Nucleophilic
substitution
© www.chemsheets.co.uk AS 1140 2-Feb-2016
g. 2-chloropropane + excess hot conc NH3
R X + 2 NH 3 R N H 2 + NH 4X
C H3 C H C H3 + 2 NH 3 C H3 C H C H3 + NH4Cl
Cl NH2
: NH3 H
C X C N+ H
: NH3
C H3 C H C H3
C H3 C H C H3
H N
+ H Nucleophilic
substitution
Cl
H
© www.chemsheets.co.uk AS 1140 2-Feb-2016
g. 2-bromo-3-methylbutane + excess hot conc NH3
R X + 2 NH 3 R N H 2 + NH 4X
C H3 C H3
C H3 C H CH C H 3 + 2 NH 3 C H3 C H CH C H3 + NH4Br
Br NH2
: NH3 H
C X C N+ H
: NH3 C H3
C H3
C H3 CH CH C H3
C H3 C H CH C H3
H
+
N H Nucleophilic
Br
substitution
H
© www.chemsheets.co.uk AS 1140 2-Feb-2016
C C + KOH C C + KBr + H2O
H X
• Hot, ethaanolic KOH (not warm,
aq NaOH)
• Lose X and H from adjacent C
(if there is one)
C C
• Forms alkene(s)
• Can get different alkenes H X
depending which adjacent C the
H comes from : OH-
• OH- acts as base (not Elimination
nucleophile)
© www.chemsheets.co.uk AS 1140 2-Feb-2016
g. 2-chloropropane + hot ethanolic KOH
C C + KOH C C + KBr + H2O
H X
C H3 C H C H3 + KOH C H3 C H C H2 + KCl + H2O
Cl
H H
C C H C C C H3
H X H Cl
: OH-
: OH-
Elimination
© www.chemsheets.co.uk AS 1140 2-Feb-2016
.g. 2-bromobutane + hot ethanolic KOH
C C + KOH C C + KBr + H2O
H X
C H3 C H2 C H C H3 + KOH C H3 C H CH C H3 + KBr + H2O
Br
H H
C C C H3 C C C H3
H X
H Br
: OH-
: OH- Elimination
© www.chemsheets.co.uk AS 1140 2-Feb-2016
