HaloAlkanes Flashcards
What is a halogenoalkane?
A saturated hydrocarbon with a halogen bonded to at least one carbon
Name a given halogenoalkane
Chloromethane
What explains halogenoalkanes increased reactivity relative to alkanes?
The polar carbon-halogen bond
Why do halogenoalkanes contain polar bonds?
Due to the difference in electronegativity between carbon and halogens
What kind of reactions do halogenoalkanes undergo?
Nucleophilic substitution
What is a nucleophile
A substance with a lone pair of electrons
Which three nucleophiles do halogenoalkanes react with?
OH⁻, CN⁻ and NH₃
What reagents and conditions are necessary for hydroxyl substitutions of halogenoalkanes?
Reflux in aqueous solution of NaOH
What reagents and conditions are necessary for nitrile (cyanide) substitution of halogenoalkanes?
Aqueous, alcoholic KCN
What is the importance of nucleophilic substitution with cyanide ions?
Increases the length of the carbon chain
What reagents and conditions are necessary for ammonia substitution of halogenoalkanes?
Reflux in aqueous, alcoholic excess ammonia
Why is excess ammonia required in its nucleophilic substitution with a halogenoalkane?
To prevent further substitutions
Draw a nucleophilic substitution mechanism for a given halogenoalkane reacting with a given nucelophile
CH3Cl + HCN- -> CH3CN + HCl
How is the rate of reaction dependent on the enthalpy of the C-X bond?
The greater the enthalpy of the C-X bond, the greater its strength, the slower the reaction
What is the trend in C-X reaction rates
Increases down the group from C-F to C-I