Chapter 27 - Amines, Amino Acids & Polymers

Amines are derived from ammonia (NH3) in which one or more hydrogen atoms have been replaced by a carbon chain or ring

The number of R groups bonded to the N 1 = primary 2 = secondary 3 = tertiary

We use amine ending Ethyl amine

We use the amine prefix (amino) 2-aminobutane

Use di/tri prefix for the alkyl group Dimethyl amine

We use the N substituted derivative (N is used just like we use numbers to indicate position it just shows that the group is connected to the nitrogen) - first fine the longest carbon chain, this is the alkyl ending with amine - find the positions of the other groups, if attached to the nitrogen then used N- to indicate this N-ethyl-N-methylpropylamine ch

As the lone pair of electrons on the N atom can accept a proton - when amine accepts this proton, a dative covalent bond forms (like the formation of ammonium from ammonia)

Notes!

Amine + acid -> ethylammonium ion

LOWEST Ethane: - London forces only - little energy needed to break weak London forces Ethylamine: - hydrogen bonds - stronger intermolecular forces require more energy to break Ethanol: - stronger hydrogen bonding than athletes amine because O is more electronegative than N (O-H is more polar than N-H) - stronger intermolecular forces require more energy to break Ethanol HIGHEST

Yes as they can hydrogen bind with water molecules

Nucleophile Ammonia has a lone pair of electrons that allows it to act as a nucleophile in nucleophilic substitution reactions with haloalkanes to produce amines

Excess ammonia in ethanol solvent

Haloalkane + ammonia -> primary amine + ammonium salt Haloalkane + primary amine -> secondary amine + ammonium salt Haloalkane + secondary amine -> tertiary amine + ammonium salt Haloalkane + tertiary amine -> quaternary ammonium salt CONDITIONS: all in ethanol solvent and excess of the ammonia/amine

• we don’t use a water solvent as the haloalkane would react with it to form an alcohol so ethanol is used to prevent this • excess ammonia is used to reduce further substitution of the amine group to form secondary and tertiary amines (haloalkane is more likely to react with lots of amine than the product)

Nitrogen directly bonded to a C double bond to an O

Acyl chloride + ammonia -> primary amide + HCl Acyl chloride + amine -> secondary or tertiary amine + HCl

R //O H2N- C - C H. \ OH

An amine group attached to the carbon next to the carboxyl group

20, built into proteins

Since they have both acidic and basic functional groups, they react similar to carboxylic acids and amines

Notes

Notes