3.2.5: Nucleophilic subsitution Flashcards
Nucleophilic substitution
A reaction where one functional group is substituted for another.
Nucleophile’s role in nucleophilic substitution
A nucleophile attacks a polar molecule and takes the place of a FG.
The lone pair on the nucleophile attacks the slightly positive charge on the carbon
Halogenoalkanes reactions with hydroxide ions (OH-)
Produce alcohols
Halogenoalkanes reactions with Cyanide ions (CN-)
produce a nitrile
triple bond between C and N in CN- (cyanide ion)
Halogenoalkanes reactions with ammonia
produce amines
lone pair on NH3 molecule
Three types of nucleophilic substitution reactions
OH-
CN-
NH3
Reactivity of halogenoalkanes decided by
carbon-halogen bond strength
as the bond needs to break for a reaction to occur
C-F bond = strongest so least reactive.
How many bonds formed and broken during a nucleophilic substitution reaction
1 bond broken
1 bond formed
Conditions for nucleophilic substitution with OH-
warm (aq) NaOH or KOH
Conditions for nucleophilic substitution with CN-
warm w/ ethanolic KCN
Conditions for nucleophilic substitution with NH3
warm w/ excess ethanolic ammonia