T7: Haloalkanes Flashcards
how are haloalkanes formed
by reacting an alkane with a halogen
name of the mechanism of how haloalkanes are formed
free-radical substitution
one essential condition for free-radical substitution
UV light
why is UV light essential for free-radical substitution
provides energy required to break the halogen-halogen bond and start the reaction
free radical definition
a species with an unpaired electron
3 stages of free-radical substitution
Initiation
Propagation 1
Propagation 2
Termination
initiation (reaction between methane and chlorine)
Cl2 -> 2Cl·
propagation 1 (reaction between methane and chlorine)
Cl· + CH4 -> ·CH3 + HCl
propagation 2 (reaction between methane and chlorine)
·CH3 + Cl2 -> CH3Cl + Cl·
how many possibilities are there in the termination stage
3
termination (reaction between methane and chlorine)
·CH3 + ·CH3 -> C2H6
·Cl + ·Cl -> Cl2
·CH3 + ·Cl -> CH3Cl
description of termination
2 free radicals combine
name of the mechanism when another halogen molecule reacts again by free-radical substitution
further substitution
initiation (reaction between chloromethane and chlorine)
Cl2 -> 2Cl·
propagation 1 (reaction between chloromethane and chlorine)
Cl· + CH3Cl -> ·CH2Cl + HCl
propagation 2 (reaction between chloromethane and chlorine)
·CH2Cl + Cl2 -> CH2Cl2 + Cl·
termination (reaction between chloromethane and chlorine)
·CH2Cl + ·CH2Cl -> C2H4Cl2
·Cl + ·Cl -> Cl2
·CH2Cl + ·Cl -> CH2Cl2
to reduce the amount of further substitution you would
use excess haloalkane
what are curly arrows used to show
show the movement of a pair of electrons
rules for curly arrows -> must start from:
- a lone pair of electrons
- covalent bond
rules for curly arrows -> must go to:
- partially positive / positive atom
- somewhere a bond is being formed
nucleophile definition
electron pair donor
3 different nucleophiles that react with haloalkanes
:OH-
:C-N
:NH3
what do substitution reactions always involve
one group / atom replacing another group / atom in a molecule
nucleophilic substitution by OH- ions -> reagent?
NaOH or KOH
nucleophilic substitution by OH- ions -> conditions?
Aqueous solvent
nucleophilic substitution by OH- ions -> type of product?
alcohol
nucleophilic substitution by OH- ions -> what is the nucleophile in this reaction?
OH-
nucleophilic substitution by OH- ions -> this reaction is a substitution reaction because…?
OH substitutes for Br
nucleophilic substitution by OH- ions -> overall reaction?
CH3CH2Br + NaOH -> CH3CH2OH + NaBr
nucleophilic substitution by C-N ions -> reagent?
KCN
nucleophilic substitution by C-N ions -> conditions?
Aqueous + ethanol solvent
nucleophilic substitution by C-N ions -> type of product?
Nitrile
nucleophilic substitution by C-N ions -> what is the nucleophile in this reaction?
C-N
nucleophilic substitution by C-N ions -> this reaction is a substitution reaction because…?
CN swapping for Br
nucleophilic substitution by C-N ions -> overall reaction?
CH3CH2Br + KCN -> CH3CH2CN + KBr
nucleophilic substitution by NH3 ions -> reagent?
excess ammonia
nucleophilic substitution by NH3 ions -> conditions?
ethanol solvent, heat and pressure
nucleophilic substitution by NH3 ions -> type of product?
amine
nucleophilic substitution by NH3 ions -> what is the nucleophile in this reaction?
:NH3
nucleophilic substitution by NH3 ions -> this reaction is a substitution reaction because…?
a Br atom has been swapped for an NH2 group
nucleophilic substitution by NH3 ions -> overall reaction(s)?
C2H5Br + NH3 -> C2H5NH2 + HBr
C2H5Br + 2NH3 -> C2H5NH2 + NH4Br
elimination -> reagent?
NaOH or KOH
elimination -> conditions?
Ethanolic solvent (alcoholic)
elimination -> type of product?
alkene
elimination -> in this reaction the OH- ion acts as a…?
base (proton acceptor)
elimination -> this reaction is a elimination reaction because…?
A H atom and a Br atom have been removed from the reactant molecule
elimination -> overall reaction?
CH3CHBrCH3 + NaOH -> CH2=CHCH3 + NaBr + H2O