Esters, Amines, Amides, Polymers & Analytical Techniques

What is the general rule for naming esters

Alcohol part comes first (name it like a branch - methyl, ethyl, phenyl)

Ending is the anion of the carboxylic acid (e.g ethanoate, butanoate)

Examples:

What are the physical properties of esters

• ______ melting and boiling point than carboxylic acids because _________

• Usually insoluble because _____________

• Sweet fruity smell

What are the physical properties of esters

• Lower melting and boiling point than carboxylic acids because esters can’t form hydrogen bonds

• Usually insoluble because esters can’t form hydrogen bonds with water

• Sweet fruity smell

How can esters be formed from carboxylic acids and alcohols. Include the conditions and type of reaction

Condensation Reation

Heat under reflux

Concentrated H2SO4 catalyst

What is a primary, secondary and tertiary amine

Physical properties of amines

• Higher melting and boiling points than expected because _________

• They are soluble in water because _________

• They have a distinctive _____ smell

Physical properties of amines

• Higher melting and boiling points than expected because they form hydrogen bonds

• They are soluble in water because they form hydrogen bonds with water

• They have a distinctive fishy smell

Chemical properties of amines:

Due to their lone pair they can act as

• __________

• __________

• __________

• Bases (proton acceptors)

• Nucleophiles (electron pair donor)

• Ligand (DM topic)

Amines are bases and so will react with acids to form salts. Show the equation of the reaction between methyl amine and HCI

Soluble amines form alkaline solutions in water. Show the ionic equation for methylamine in water

Amines can act as nucleophiles (like ammonia).

Show how amines can react with haloalkanes to form secondary amines

Amines can act as nucleophiles (like ammonia)

Show how amines can react with aceyl chlorides to form an amide

Use CH3COCl as your aceyl chloride

What are primary, secondary and tertiary amides

Show how amides can be hydrolysed in both acid and alkali conditions - give the conditions required

Heat under reflux

Define the term polymer

Polymers are long chain molecules made by joining many thousands of smaller molecules (monomers) together

Define the term addition polymer

Monomers added together forming a long chain in an addition reaction. Only 1 product with 100% atom economy. Monomers contain C=C

What is a condensation polymer and what are its properties

Small molecule (H2O or HCl) lost when monomer molecules join in condensation reaction to form long chain.

Monomers must contain 2 reactive functional groups (e.g. COOH and OH to form polyesters or COOH and NH2 to form polyamides)

Polyamides and polyesters are condensation polymers

Show how diamines and dicarboxylic acids react in a condensation reaction to form polyamides. Give the reagents and conditions

If a Nylon (Polyamide) is called Nylon 6,10 what do the numbers mean

First number - 6 carbons in diamine

Second number - 10 carbons in dicarboxylic acid

Show how a polyamide can be made from a single monomer containing both an amine and carboxylic acid

Show how diols and dicarboxylic acids react in a condensation reaction to form polyesters. Give the reagents and conditions

Show how diols and diacyl chlorides react in a condensation reaction to form polyesters. Give the reagents and conditions

Breaking down condensation polymers

• Break all ____ and ___ bonds

• Add water - put an OH on the C=O forming the ______ group and but a H on the -O/-N to make an _____/_____ group

• Alkaline conditions - _____ groups form salts e.g. ____Na+

• Acidic conditions - _____ groups form salts e.g. ____Cl-

Breaking down condensation polymers

• Break all ester and amide bonds

• Add water - put an OH on the C=O forming the carboxylic acid group and but a H on the -O/-N to make an alcohol/amine group group

• Alkaline conditions - COOH groups form salts e.g. COO-Na+

• Acidic conditions - NH2 groups form salts e.g. NH3+Cl-

Mr is given to how many decimal places on a high resolution mass spectrum

4d.p.

NMR Spectrum is used to find

• The number of different hydrogen ______ in a molecule

• The number of hydrogen atoms in each _________

• The type of chemical environment

• The number of hydrogen atoms attached to the _______ carbon atoms

• The number of different hydrogen environments in a molecule

• The number of hydrogen atoms in each environment

• The type of chemical environment

• The number of hydrogen atoms attached to the adjacent carbon atoms

What is CDCl3 used for in NMR

Acts as a solvent for sample

Causes no peak due to having no hydrogen environments

What is TMS used for in NMR

Used as a reference peak as it gives a strong peak, furthest to the RHS

How is an H NMR spectrum interpreted

• Relative peak area =

• Chemical shift =

• Splitting pattern =

• Relative peak area = number of hydrogen in environment

• Chemical shift = position of peak, chemical environment/group

• Splitting pattern = n-1 = number of adjacent carbons on adjacent carbon

How is C NMR interpreted

• Number of peaks =

• Chemical shift =

• Number of peaks = number of carbon environments

• Chemical shift = indicates type of carbon environment

How many different carbon enviroment are there in a benzene ring

1 environment

How many different carbon environments are in a phenol

4 environments