Please enable JavaScript.
Coggle requires JavaScript to display documents.
Halogenoalkanes - Coggle Diagram
Halogenoalkanes
-
Properties
-
-
-
C-X bond in HA is polar
- halogen atoms MORE electronegative
than C atom
- electronegativity decreases
down Group VII
- so C-X bond less polar
-
-
Uses
-
-
-
-
2-bromo-2-chloro-1,1,1-trifluoroethane
(halothane) - used as anaesthetic
Preparation
made from alkanes,
alkenes + alcohols
-
Reactivity
Nucleophilic
Substitution
reaction with
water
-
rate of hydrolysis depends on
halogen in HA
- depends on strength of C-X bond
- lower bond enthalpy, weaker it is
and more easily broken
(slowest = C-F, fastest = C-I)
as halide ions produced,
react with aq silver ions in
silver nitrate
= form insoluble silver
halide precipitates
-
-
-
reaction with
cyanide ion
-
- HA refluxed with ethanolic solution
of K/Na cyanide
- product = nitrile = contains 1
more C atom than HA used in reactant
- useful in organic synthesis
reaction with
ammonia
-
-
yield of primary amine (1 C attached to N)
raised by use of concentrated solution of ammonia
- why? greater chance of HA reacting with
it as nucleophile
- FORMING - secondary/tertiary amine
- primary amine acts a nucleophile
itself as N has lone pairs of e-
- more reactive than in ammonia
due to inductive effect of alkyl group
- nucleophile attracted to δ+ charge
on C atom attached to halogen atom
& forms bond with it
- X removed from organic molecule
as C-X bond breaks
- pair of e- in bond ends up on X
so leaves halide ion - X-
Elimination
-
HA converted to alkene
hydroxide ion acts as base, accepting
hydrogen ion from HA to form water
-
- C-X bond polar - w slight
positive (δ+) on C
- species w lone pair of e-
attracted to area of low
electron density - nucleophiles
-