1.AMINES N AMIDES

if a hydrogen from ammonia is replaced with an akyl group/aromatic group

you get an amine

i hydrogen replaced

primary amine

2 hydrogen replaced

secondary amine

3 hydrogen replaced

tertiary amine

4th organic group added

quaternary ammonium ion

quaternary ammonium ions are positively charged

attracted to negative ions to form quaternary ammonium salt complexes

ammonium salt example

tetramethylammonium chloride

small amines smell slightly fishy

large amines smell very fishy

amine suffix

-amine/-amine ion

surfactants

compounds partially soluble/ insoluble in water

some quaternary ammonium compounds can be used as cationic sufactants

positively charged surfactants

cationic ammonium compound surfactants have at least 1 long hydrocarbon chain

long hydrocarbon chain is insoluble in water

and binds to non polar substances like grease

positively charged head group is soluble

in water

cationic surfactants are good detergents

the non polar part binds to grease and the polar part dissolves in water allowing spots of grease to mix with water and be washed away

cationic surfactants are used in things like

fabric conditioners and hair products

when hair/ fabrics get wet they pick up negative charges on their surface

positively charged parts of the cationic surfactant is attracted to these negatively charged surfaces to form a coating over the surface

the coating prevents the build up of static electricity

this is important to keep the fabric smooth in fabric conditioners and hair flat in hair products

amines act as weak bases

because they accept protons due to the lone pair of electrons on the nitrogen atom that forms a coordinate bond

the avaliability of the lone pair electrons on nutrogen

affects its strength as a base

the more avaliable the lone pair

the stronger the base

a lone pair of electrons will be more available

if its electron density is higher

primary aromatic amine are WEAK bases

because benzene ring draws electrons towards itself and the nitrogen lone pair gets partially delocalised onto the ring

electron density on nitrogen decreases

making the lone pair less avaliable

alaphatic amines

amines w akyl groups

primary alaphatic amines are strong bases

because the akyl group poushes electrons onto attached groups

electron density on nitrogen atom increases

making lone pair more available

amides are a derivative of carboxylic acids

-CONH₂

naming

-amide suffix

n substituted amides

amides where 1 hydrogen has been substituted for an akyl group

n substituted naming

N-Methyl/ethly/propyl

heating halogenoalkanes w excess ethanolic ammonia forms

aliphatic amines

this process can produce a mixture of primary secondary and tertiary amines and quaternary ammonium salts as more than 1 hydrogen can be substituted

halogenoalkane nuceophilic substitution to produce amines

1. NH3 attacks ð+ carbon attacked to halogen

2. carbon donates electons to halogen from its broken bond as it forms a new one with ammonia

3. forms an akylammonium salt + negatively charged halide ion

4. second ammonia molecule donates its lone pair of electrons to a hydrogen attached to first ammonia

5. this hydrogen breaks from the akyl ammonium salt and joins ammonia to form NH₄⁺ ion

6. products are a primary amine, NH4+Halide complex

the amine product still has a lone pair of electrons on the nitrogen

so it can still act as a nuceophile meaning further substitutions will take place till a quaternary ammonium salt is formed

nitrile reduction ujsing LiAlH4 in dry ether and dilute acid forms

amines

LiAlH4 is tooe xpensive for industrial use

the industry uses a metal catalyst: platinum/nickel at high temperature n pressure in a process called catalytic hydrogenation

acyl chlorides react w ammonia to form primary amides: nuceophilic addition elimination

and acy chlorides react with AMINES o form n substituted amides: nuceophilic addition-elimination

nuceophilic addition elimination mechanism step 1

• lone pair of electrons on nitrogen attacks ð+ carbon on acyl chloride

• pair of electrons transfer to Oxygen from C=O

• pair of electrons on oxygen return to reform double bond and chlorine is kicked off w electrons from C-Cl transfered to it making it negative

• leaving positively charged amide ion and negatively charged chloride ion

nucleophilic addition elemination reaction part 2

• Cl- bonds w hydrogen from nutrogen aotm

• pair of electrons transfered onto nitrogen atom from the bond

• this names amide and HCl

acid anhydrides also react w primary amines/ ammonia to form

amides and carboxylic acid

acid anhydrides + primary amines forms

n substituted amides

acid anhydride + ammonia forms

primary amide

reducing nitro compounds like nitrobenzene forms

aromatic amines

methodology

nitrobenze + tin + conc HCl is reated under reflux to form salt

salt is turned into an aromatic amine, using sodium hydroxide solution