Nitrogenous compounds + polyesters module 6

amine structures ( Image)

N attached to 1 R group = primary

N attached to 2 R group = secondary

N attached to 3 R group = tertiary

what are type of molecule are amines

Bases

lone pair on N accepts protons

How to name amines

Suffix - amine

prefix - Alkyl group (alphabetical order )

amine + acid →

Amine + Acid → Salt

(Amine + Acid ) explanation

NH₂ acts as base and accepts proton

Acid ion ionically bonds to N⁺H₃

Phenylamine + Nitric acid ( Image)

Amine + Acid how to name salt

Alkyl ammonium ion

How to make an aliphatic amine reaction

Haloalkane + Excess NH₃ dissolved in ethanol → Primary amine + ammonium halide

What do amines act as in nucleophilic substitution reactions

Nucleophile → electron pair donor

Why do we use excess NH₃

Prevents further substitutions

no undesired secondary / tertiary amines

How to make a aromatic amine equation

Reduce nitrobenzene → Phenylamine

Reactants to make primary amine

Haloalkane

excess NH₃ dissolved in ethanol

By product of making a primary amine

Ammonium halide

Why is NH₃ dissolved in ethanol

Prevents H₂O from reacting with haloalkane → produces alcohol

Conditions to form a phenylamine

Sn/ HCl

reflux

How many [ H ] to reduce 1 nitro group on nitrobenzene to form phenylamine

6 [ H ]

forming a aromatic amine word equation

C₆H₅NO₂ + 6 [ H ] → C₆H₅NH₂ + 2H₂O

forming aromatic amine by product

2 H₂O

Forming aromatic amine ( Image)

Amide structure ( Image)

CON bond

Amide structures ( Image)

How to name primary amides

look at alkyl group then add amide

Name this structure

Benzamide

How to name secondary amines

Add N then Group attached to carbonyl = Stem + amide

R Group directly attached to N → Prefix

How to name tertiary amides

N,N then R group attached to N → prefix ( alphabetical order)

R attached to carbonyl = stem + amide

Primary to secondary amine mechanism

what are the ways to make a Amine

Haloalkane → Nitrile → Amine

Haloalkane + Excess NH₃ dissolved in ethanol

Acyl chloride + NH₃

Advantages of Nitrile to amine

makes only 1 product ( amine)

don’t have to purify mixture of products

How to form amine from Haloalkane ( Nitrile method)

React with KCN ( dissolved in ethanol) to form a nitrile ( 1 more carbon)

react nitrile with 2H₂ → Amine

Conditions for nitrile to amine

React with 2H₂

Nickel catalyst

ways to make a amide

Acyl chloride / acid anhydride + amine → secondary amide

what are optical isomers

Form non- imposable mirror images

Reagants and conditions for Nitrile to carboxylic acid

H₂O / HCl

Number of structural isomers ( Image)

what are the types of polymers

Addition

Condensation

Difference between addition and condensation polymers

Condensation → Biodegradable

Addition → Non -biodegradable

Carboxylic acid + Amine →

Carboxylic acid + Amine → Amide + H₂O

what are the 2 monomers of polyester

Dicarboxylic acid + Diol → polyester + H₂O

hydroxycarboxylic acid + hydroxycarboxylic acid + H₂O

Product of all acyl chloride reactions

HCl

what are the 2 monomers of polyamide

Amino acid + Amino acid

Dicarboxylic acid + Diamine

what are the polymers of amino acids

Polypeptide

Dicarboxylic acid + Diol reaction explained

Diol → loses H

Dicarboxylic acid → Loses OH

Dicarboxylic acid + Diamine reaction explained

Diamine → loses a H

Dicarboxylic acid → loses OH

Hydroxycarboxylic acid (image)

General formula for making polymer

n Reactant + n Reactant → polymer n + 2n-1 H₂O

Making polyester ( Image)

How to work out monomers of Polyester

Break through ester bond

monomers → Diol + Dicarboxylic acid

Monomers of PEN

Dicarboxylic acid + Diamine reaction explained

Diamine → Loses H

Dicarboxylic acid → loses OH

Forming polyamide ( Image)

Hydrolysis of polymers general equation ( Image)

disadvantages of water in hydrolysis

Too slow

use Hot aqueous acid / alkali

Products of acid hydrolysis on polyester

Dicarboxylic acid + Diol

Polyester acid hydrolysis ( Image)

Reactants in hydrolysis reaction

(Polymer) n + n H₂O

Monomer of acid hydrolysis of polymer with one ester bond

amino acid

hydroxycarboxylic acid

Products of alkali hydrolysis on polyester

Dicarboxylate salt + Diol

Base hydrolysis polyester ( Image)

what are the types of Hydrolysis

Acid

Base

products of the acid hydrolysis of Polyamides

Dicarboxylic acid

Diammonium ion

Acid hydrolysis of polyamides ( Image)

what is meant by a chiral centre

Carbon has 4 different groups attached

when are carbons never chiral

Two or more hydrogens attached

C=C

How many optical isomers do molecules with 1 chiral centre have

2 optical isomers

How many optical isomers do molecules with 2 chiral centres have

4 optical isomers

Which molecules are always chiral

Amino acids

What are Enantiomers

Optical isomers

How to work out number of optical isomers a chiral centres form

Is benzene chiral?

No

addition polymers (image)

everything revolves around broken C=C bond

TLC question on Aspirin image

melting of pure aspirin was 138 - 140

impure 130 - 140

What does the Amine group ( NH₂) contain

Hydrogen bonding