FC18: Haloalkanes Flashcards
State 3 ways haloalkanes can be prepared
from alkanes (UV light with halogen)
from alkenes (with halogen or hydrogen halide)
from alcohols (sodium halide and concentrated sulfuric acid)
what are the conditions for making bromoethane from ethanol and hydrogen bromide
sodium bromide, concentrated H2SO4, and heat under reflux
what does heat under reflux do
makes sure no gas is lost
what does in situ mean
situated in the original place (undisturbed)
what does hydrolysis mean
a reaction where a covalent bond is broken through the reaction with water
what is formed when you hydrolyse bromoethane
ethanol and hydrogen bromide
what is a nucleophile
electron pair donor
why is the reaction between bromoethane and water slow? what is used instead
because water is a poor nucleophile, so aqueous NaOH is used instead
what is the mechanism in the hydrolysis of haloalkanes
nucleophilic substitution
what is bond enthalpy
the energy needed to break a bond
what has the highest rate of hydrolysis out of the haloalkanes, with chlorine, bromine, iodine
the C-I bond has the lowest bond enthalpy, so the activation energy for the hydrolysis of the iodoalkane will be the lowest and the rate of hydrolysis for the iodoalkane will be highest
write out the experiment to compare the rate of hydrolysis of different haloalkanes
Add aqueous silver nitrate to the haloalkanes dissolved in ethanol
Place into a water bath to maintain the same temperature
why is ethanol used in the experiment to compare the rate of hydrolysis of different haloalkanes
it is a solvent for both partly non-polar haloalkanes and ionic AgNO3
it dissolves the ionic AgNO3 via ion-dipole bonds and the partly non-polar haloalkane via London forces. Ethanol can also form H-bonding with water
what is formed and write the equations when you carry out the experiment to measure the rate of hydrolysis of bromopropane
bromopropane + water -> propanol + H+ + Br- (HBr)
Ag+ + Br- -> AgBr (cream precipitate)
why are bromide ions produced faster from the hydrolysis of the bromoalkane than chloride ions from the chloroalkane
because of the smaller bond enthalpy for the C-Br bond than the C-Cl bond