3.3 Halogenoalkanes Flashcards
What is the termination step in free radical substitution, use methane & chlorine as an example
Where two radicals react together
Define a free radical
Species with an unpaired electron
Write an equation for each of the following steps in the mechanism for the reaction of chloromethane with chlorine to form dichloromethane
Haloalkanes produced from free radical substitution can react again with another halogen and undergo further substitution. How to prevent further substitution
Use excess alkane
What are CFCs, state what they cause
Haloalkanes that contain both chlorine and fluorine
They cause depletion of ozone layer
Write three equations to show how trichlorofluoromethane is involved in damaging the ozone layer
Why does fluoroethane not lead to the depletion of ozone
Doesn’t contain a chlorine
C-F bonds are strong and do not break
Define a nucleophile
An electron-pair donor
The different nucleophiles that react with haloalkanes in nucleophilic substitution
Draw mechanism for nucleophilic substitution with NH3, CN and OH. Use bromoethane
Reagent and conditions for nucleophilic substitution with OH^-
Reagent : NaOH or KOH
Conditions : aqueous solvent
Reagents and conditions for nucleophilic substitution by CN^-
Reagent : KCN
Conditions : water and ethanolic solvent
Reagent and conditions for nucleophilic substitution by NH3
Reagents : Excess NH3
Conditions : Ethanol solvent, heat and pressure
What is rate of a reaction equal to
1 / time
Describe method for hydrolysis
Reasons for different rates of hydrolysis
As bond enthalpy decreases, it is easier to break C - halogen bond
Weaker the bond, the faster the rate
Name of mechanism from haloalkane to alkene
Reagents :
Conditions :
Electrophilic addition
Reagents : NaOH or KOH
conditions : hot & ethanolic solvent
Outline eliminations for 2-chlorobutane and draw all possible products
State use of CFC’S
They are used as refrigerators
D
Initiation step for CH3F in free radical substitution
F2 -> .2F
State conditions necessary for free radical substitution
UV light
High temperature
Linked to free radical substitution
C2H6 + 6Br2 -> C2Br6 + 6HBr
State why ultraviolet light is needed in free radical substitution, use chlorine as an example
Provides enough energy to break covalent bonds in chlorine to form free radicals
In ozone depletio, for formation of reactive species, what are you trying to form
A chlorine free radical
B as it doesn’t contain chlorine
C-Br bond is weaker than C-Cl bond as C-Cl bond has higher bond enthalpy
Explain how an atom can act as a catalyst
Not being used up in reaction
Being unchanged at the end
Is regenerated
Chlorofluorocarbons are banned in many countries because of their effect on the environment. Why can a single radical cause the decomposition of many molecules in the ozone layer
Cl. (Radical) is regenerated and causes a chain reaction in the decomposition of ozone
What does the dot represent in a radical atom
An unpaired electron
Write an overall equation to represent the decomposition of ozone into oxygen
2O3 -> 3O2
State benefit to life on Earth of ozone in the upper atmosphere
Absorbs harmful UV radiation
State how a CFC can contribute to global warming
Absorbs infrared radiation as molecule has polar bonds
State how CFCs from chlorine atoms in the upper atmosphere
C- Cl bonds break
Define nucleophile
Electron pair donor
Electron pair donor
CH3CH2Br reacts with NH3 to produce CH3CH2NH2, state why an excess of ammonia is needed in this reaction
To minimise further substitution as ethylamine can react further to form secondary amines
Name compound CH3CH2CN
Propanenitrile
What compounds needed for nucleophilic substitution and which one usually involved in a bigger mark question as it has more steps
NH3
KCN
KOH / NaOH
NH3 has more steps than the others
Sign is plus
Skip part a)
Only do second part
Lower concentration
Lower temperature
Use water as an aqueous solvent
What type of stereoisomers are E- Z isomers
Geometrical isomers
State reagent in elimination and it’s role in the mechanism
Reagent : NaOH / KOH
Role : base
C because it is an alcohol
For nucleophilic substitution, state the role of hydroxide ions is in the mechanism
Nucleophile / electron pair donor / lone pair donor
Bromethane can undergo nucleophilic substitution, state the characteristic that enables it to undergo this reaction
There is a polar C-Br bind
Conditions of elimination
- ethanolic solvent
- concentrated hydroxide
- high temperature
If a warm dilute concentrated aqueous sodium hydroxide reacts with a haloalkane, what mechanism is this and what does it form
Nucleoliphilic substitution
Alcohol