17.5
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what are amines
nitrogen containing compounds
explain the structure of an amine
3 bonding pairs with at least one alkyl group 1 lone pair trigonal pyramidal shape
what is a primary amine
nitrogen is attached to 1 alkyl group
what is a secondary amine
nitrogen is attached to 2 alkyl groups
what is a tertiary amine
nitrogen is attached to 3 alkyl groups
whats the name of the compound C6H5NH2
phenylamine
what is the equation for the preparation of a primary amine from a halogenoalkane
CH3Cl + NH3 -> CH3NH2 + HCl
what is the equation for the preparation of a secondary amine from a halogenoalkane
CH3Cl + CH3NH2 -> (CH3)2NH + HCl
what are the 2 ways of forming amines from halogenoalkanes
heating with ammonia under pressure in a sealed container or mix with aqueous ammonia
how does the formation of amines from halogenoalkanes involve and nucleophilic attack
lone pair on ammonia act as nucleophile and attack the electron deficient carbon, the amine formed then acts as a nucleophile and attacks another electron deficient carbon to form a secondary amine
how can the number of secondary amines being formed from the products of halogenoalkanes and ammonia be reduced
ammonia is used to excess so that it outnumbers the molecules of primary amines formed and some of the excess ammonia reacts with the HCl to form NH4Cl
what is the equation for the reduction of ethanenitrile
CH3CN + 4[H] -> CH3CH2NH2
what are the conditions and the reagent for the reduction of nitriles to primary amines
reducing agent - lithiumtetrahydridoaluminate mixed in dry ether
why must the reduction of nitriles to primary amines be in dry ether
so that no water can affect the reaction
whats the equation for the reduction of nitrobenzene
C6H5NO2 + 6[H] -> C6H5NH2 + 2H2O
what are the reagents and conditions for reduction of nitrobenzene to phenylamine
reducing agent (tin) and concentrated hydrochloric acid heated under reflux
how does phenylamine react with acids
forms phenyl ammonium ion (C6H5NH3+)
how can phenyl ammonium ion be converted back to phenylamine
added alkali (sodium hydroxide) C6H5NH3+ + OH- -> C6H5NH2 + H2O
what are phenylamines commonly used for
dying blue jeans manufacturing polymers pharmaceuticals
what is the trend in solubility of primary aliphatic amines as hydrocarbon chain decreases
as hydrocarbon chain increases solubility decreases
why are amines soluble in water
their lone pair on the nitrogen allows them to form hydrogen bonds with the water molecules
how can amines act as a base when mixed with water
the nitrogen uses its lone pair to form a dative bond with the hydrogen on the water molecule CH3NH2 + H2O <=> CH3NH3+ + OH-
how does ammonia act as a base when mixed with water
the nitrogen uses its lone pair to form a dative bond with the hydrogen on the water molecule NH3 + H2O <=> NH4+ + OH-
what is basicity
the extent to which a base can donate a lone pair of electrons to the hydrogen atom of a water molecule