AMINES AND CARBOXYLIC ACID DERIVATIVES Flashcards
What is an amine?
The functional group of an amine is a nitrogen
How are amines classified?
Primary: A nitrogen with 2 hydrogens and one substituent
Secondary: A nitrogen with one hydrogen and 2 substituents
Tertiary: a nitrogen with 3 substituents attached
Define aliphatic and aromatic amines
Aliphatic: all carbons bonded to nitrogen are derived from alkyl groups
Aromatic: one or more of the groups bonded to nitrogen are aryl groups
Define heterocyclic aliphatic amines:
Define heterocyclic aromatic amines:
a heterocyclic aliphatic amine in which the ring is saturated (has no C=C bonds)
A heterocyclic aromatic amine is when the amine nitrogen is part of an aromatic ring.
How to name amines:
Drop the -e of the parent alkane and replace it with -amine
Use a number to locate the amino group on the parent chain
How do you name unsymmetrical secondary and tertiary amines?
Name them as N-substituted primary amines
Take the largest group bonded to nitrogen as the parent amine
Name the smaller group(s) bonded to nitrogen and show their location on nitrogen by using the prefix N- (indicating that they are bonded to nitrogen
List some physical properties of amines
- amines are polar compounds
- Both primary and secondary amines have N-H bonds and can form H bonds with one another
- tertiary amines have no N-H bond and cannot for H bonds
- Low molecular weight amines are completely soluble in water
- Higher-molecular-weight amines are only moderately soluble in water or are insoluble
- Solubility decreases as molecular weight increases
What is the functional group of an ester?
A carbonyl group bonded to an -OR group
How to name an ester?
Both IUPAC and common names of esters are derived from the names of the parent carbonyl carbon
Name the alkyl or aryl group bonded to oxygen first, followed by the name of the acid; replace the suffix -ic acid by -ate
A cyclic ester is called a lactone
List some physical properties of esters
Polar molecules, dipole-dipole interactions, BP is similar to those of aldehydes and ketones with same molecular weight
Do not form H bonds, their BP are much lower than those of carboxylic acids with similar weight
smaller esters are somewhat soluble in water, due to the ability to form H bonding, but decreases with increasing molecular weight
Explain the hydrolysis and saponification of esters
Hydrolysis is a chemical decomposition involving breaking a bond and the addition of the elements of water
Hydrolysis of esters in aqueous acid is the reverse of Fischer esterification, a large excess of water drives the equilibrium to the right to form the carboxylic acid and alcohol
Saponification is the hydrolysis of an ester using a hot aqueous base such as NaOH
Explain the polymerisation of esters (polyesters)
The first polyester involved polymerisation of this dieter and diol
step-growth polymers: formed by reaction between two molecules, each of which contains 2 functional groups. Each new bond is created in a separate step
Explain the reaction of esters and amines
esters react with ammonia and with primary and secondary amines to form amides (carbonyl group attached to a nitrogen atom)
What is the functional group of an amide?
A carbonyl group bonded to a nitrogen atom
How do you name an amide?
To name an amide, drop the suffix -oic acid from the IUPAC name of the parent acid, and add -amide
If the amide nitrogen is also bonded to an alkyl or aryl group, name the group and show its location on nitrogen by N-; two alkyl or aryl groups by N,N-di-
