halogenoalkanes Flashcards
general formula halogenoalkanes
CnH2n+1Hal
functional group
C-Hal
what does the presence of the polar bond in halogenoalkanes mean
they’re more reactive than alkanes
3 uses of halogenoalkanes
- refrigerants
- solvents
- pharmaceuticals
how are halogenoalkanes named
after the parent alkane with the prefix chloro, bromo, iodo etc.
what must be indicated if there are more than 3 carbon atoms in the molecule
the position of the halogen
what must be indicated if 2 or more halogens are present
their positions in the chain
how are the halogens named if there are 2 of them in the chain and they are different
in alphabetical order
what 2 reactions do halogenoalkanes take part in
nucleophilic substitution and elimination
what is the halogen atom replaced with in a nucleophilic substitution reaction
by a new group of atoms
nucleophile
electron pair donor
why do halogenoalkanes take part in nucleophilic substitution
the carbon is bonded to a halogen and so it is rendered electron deficient
where does the nucleophile donate its pair of electrons to in nucleophilic substitution
the delta plus c atom to form a new bond
how does the C-Hal bond break in nucleophilic substitution and what does it form
Heterolytic fission
halide ion formed
examples of common nucleophiles
hydroxide
cyanide
ammonia
what do halogenoalkanes react with aqueous hydroxides to form
alcohols
what is the reaction between halogenoalkanes and aqueous hydroxides often referred to as
hydrolysis
hydrolysis
the breaking of a bond using water
what is the reagent in nucleophilic substitution with aqueous hydroxides
the hydroxide
what conditions are needed for nucleophilic substitution using hydroxide
warm and aqueous
general equation for the nucleophilic substitution between halogenoalkane and hydroxide
R-Hal + NaOH > R-OH + NaHal
reagent for nucleophilic substitution between halogenoalkane and cyanide
cyanide ion
conditions for nucleophilic substitution between halogenoalkane and cyanide
warm and ethanolic
general equation for for nucleophilic substitution between halogenoalkane (bromo) and (potassium) cyanide
RBr + KCN > RCN + KBr
what does reacting a halogenoalkane with cyanide increase
the length of the carbon chain
what do halogenoalkanes react with excess ammonia to form
amines
reagent for nucleophilic substitution between halogenoalkane and ammonia
NH3
conditions for nucleophilic substitution between halogenoalkane and ammonia
ethanolic and warm
general equation for nucleophilic substitution between halogenoalkane and ammonia
R-Hal + 2NH3 > RNH2 + NH4 + Hal-
what does the rate of substitution reactions of halogenoalkanes depend on
the c-hal bond enthalpy
what does a halogenoalkane react to form in an elimination reaction
an alkene
elimination
a reaction in which an atom/group of atoms is removed from a reactant
reagent for elimination reaction with halogenoalkanes
hydroxide
conditions for elimination reaction with halogenoalkanes
HOT and ethanolic
sequence of events in elimination reactions with halogenoalkanes
- halogen atom always removed
- H atom from an adjacent C atom also removed
- double bond forms between the two C atoms
what is the role of the hydroxide in elimination with halogenoalkanes
base
substitution vs elimination using hydroxide: conditions
s: warm and aqueous
e: hot in ethanol
substitution vs elimination using hydroxide: major product
s: alcohol
e: alkene
substitution vs elimination using hydroxide: role of OH-
s: nucleophile
e: base
what properties of chloroflourocarbons make them suitable for use as solvents and refrigerants
non-toxic and low reactivity
what did the properties of chloroflourocarbons lead to
the depletion of the ozone layer
where does ozone form
in the upper atmosphere
how does ozone form
from the reaction of oxygen atoms with oxygen molecules
equation for formation of ozone:
O + O2 > O3
why is the ozone layer beneficial
it absorbs UV radiation that can cause skin cancer
what did scientists discover that waste CFCs didnt do
break down easily and so would rise up to the upper atmosphere and break down to form chlorine radicals
what do chlorine radicals do and what has this led to
catalyse the breakdown of ozone
led to a hole in the ozone layer
equation for chlorine radicals reacting with ozone
O3 + Cl. > O2 + ClO.
ClO+ O3> 2O2 + Cl.
what alternatives to CFCs are now used
organohalogens that don’t contain chlorine