Amines, amides, amino acids and proteins Flashcards
Why can the ammonia molecule accept protons?
It has a lone pair of electrons
What are amines?
Compounds based on ammonia where one or more of the hydrogen atoms have been substituted for an alkyl or aryl group
How are amines formed?
Ammonia heated under pressure with halogenoalkane
What is a primary, secondary and tertiary amine?
Primary - 1 hydrogen replaced
Secondary - 2 hydrogen replaced
Tertiary - 3 hydrogen atoms replaced
How can a hydrogen atom on a primary or secondary amine be replaced?
Ethanoyl chloride or ethanoic anhydride
Substitues a CH3CO- group in
What does a n indicate in the naming of a substance?
Bonded to nitrogen atom
How are aryl amines formed?
Reduction of nitrobenzene using tin and concentrated HCl
How would aryl amines be formed in the lab?
Carried out under reflux
Flask is cooled and NaOH added to redissolve initial precipitate of Sn(OH)4
Water added and steam distillation used to separate phenylamine and water
Salting carried out (powdered NaCl added) and transferred into separating funnel
Ethoxyethane added and aequous layer run off and repeated
KOH pellets added to remove HCl and dry extract
Ethoxyethane is distilled off
What catalyst is used in industry to form phenylamine?
Iron rather than tin because it is cheaper
Why do teriary amines have lower metling and boiling temperatures than primary and secondary amines?
Hydrogen bonding possible in primary and secondary
Why are aryl amines only slightly soluble in water?
Aromatic nature of benzene ring outweighs tendancy of NH2 group to form hydrogen bonds
Are primary alkyl amines stronger or weaker bases than ammonia?
Stronger because electrons shift from the akyl group, increasing the electron density on the nitrogen atom so that it can hold a proton more strongly
Is phenylamine a stronger or weaker base than ammonia?
Weaker because the lone pair of electron on the nitrogen atom interacts with the pi electrons in the ring, reducing the electron density of the nitrogen atom
Must be a high exess of H+ form salt
Readily undergoes electrophilic substitution
How does an amine react with ethanoyl chloride?
Ethanoylation where one hydrogen atom in the nitrogen atom is exchanged for CH3CO-
HCl also formed
What is the mechanism for the ethanoylation of an mine?
1. Nitogen attracted to positive carbon Breaks bond with oxygen 2. Oxygen forms bond with carbon Carbon breaks bond with chlorine Nitrogen breaks bond with hydrogen
What simplifies the production of paracetamol?
Doesn’t produce chiral molecules
Normally considered at every stage
How is nitrous acid made?
Very unstable compound so must be made as needed and reactions must be kept below 5^C
NaNO2 + HCl –> NaCl + HNO2
What’s produced when nitrous acid reacts with a primary amine?
Alcohol
Nitrogen gas
Water
What happens when an aromatic amine reacts with nitrous acid above 5 degrees?
Alcohol eg phenol
Nitrogen gas
Water