Organic Nitrogen Flashcards
What is a primary amine?
1 carbon bonded to an NH2
What is a secondary amine?
NH bonded to 2 carbon atoms
What is a tertiary amine?
N bonded to 3 carbons
What are the conditions and reagents for forming a primary amine?
haloalkane with excess ethanolic ammonia
heated under pressure
What type of reaction is forming a primary amine from a haloalkane and excess ethanolic ammonia?
nucleo sub
How are amines able to act like a nucleophile?
there is a lone pair on the N
How do you form a secondary amine?
reacting a primary amine with a haloalkane
How can you add a NH2 group to a benzene ring? with conditions and reagents?
nitrate it first
then reduce it using conc HCl and Sn (tin) under reflux
then add NaOH
How many [H] are required to reduced nitrobenzene to phenylamine?
6
How can a amine be produced from a nitrile, give conditions and reagents?
heating with H2 with a Ni catalyst
reduction reaction
Why is the boiling point of amines higher than other substances?
they can form london forces but can also form H bonds which are stronger and takes more energy to break them
Are amines soluble in water and why?
Yes = can form H bonds to water molecules
Why is phenylamine slightly less soluble in water than other amines?
has a large, non-polar hydrocarbon part which doesnt form H bonds and makes the compound less soluble
Why are primary and secondary amines weak bases?
the lone pair on the N can accept a proton = forms a dative bond to H+
What happens when amines react with an acid?
form ammonium salts = NH3+ is present
What are amino acids?
compounds that contain both an amine group and a carboxylic acid group
What is an alpha amino acid?
the amine group and the COOH group are attached to the same carbon atom
What type of isomers do all amino acids have?
optical isomers - they have a chiral carbon
What happens when you react an amino acid with an acid?
the amine group reacts to form a salt eg. NH3+ Cl-
What happens when you react an amino acid with a base?
the COOH group reacts to form a carboxylate salt
What happens when you react an amino acid with an alcohol?
forms an ester by reacting with the COOH group
What is the general structure of primary amides?
RCONH2
(C is central)
How can primary amides be made?
condensation reaction of an acyl chloride with ammonia
What byproduct is formed when reacting ammonia with an acyl chloride?
NH4Cl
What is the general structure of a secondary amide?
R1-C=O, NH-R2
(C is bonded to O and R1 and NH)
How can secondary amides be made?
reacting an acyl chloride with a primary amine
How can you form a nitrile from a haloalkane?
nucleo sub by adding CN- dissolved in ethanol
How can you form a hydroxynitrile from a carbonyl?
adding NaCN/H+ which generates HCN which is added to the molecule
nucleophillic addition
What is the importance of adding CN to molecules?
forms C-C bonds to make larger and more complex molecules
How can a primary amine be fromed from a nitrile?
reduce the nitrile by adding H2/Ni
How can you form a carboxylic acid from a nitrile?
heat with HCl (aq) and add H2O
hydrolysis reaction
