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CHAPTER 5 AMINES
This is a mind map of amines in Chapter 5 of a certain chemistry book. The map contains 7 branches, namely: 'INTRODUCTION','CLASSIFICATION OF AMINS','IUPAC NAMING','NAMING CYLIC AMINE','NAMING AROMATIC AMINE','PREPARATION OF AMINES' and 'REACTION OF AMINES'. Suitable for people interested in chemistry or students studying amines.
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- Outline
CHAPTER 5AMINES
1)INTRODUCTION
amines are organic nitrogen compounds formed by replacing one or more hydrogen atoms of ammonia (NH3) with alkyl group.
2) CLASSIFICATION OF AMINES
3) IUPAC NAMING
find the longest continuous chain of carbon atoms determine the root name
the -e in alkane name is changed to -amine, and a number shows the position of the amino group along the chain.
other substituents on the carbon chain are given numbers, and the prefix N- is used for each substituent on nitrogen.
the prefix amino is used to indicate the presence of an -NH2 group in a molecule containing more than one functional group or in compound with complicated structure.
carboxylic acid is attached to carbon 1 and at carbon 2 there have ammonia
alcohol is attached to carbon 1 and ammonia is at carbon 2
4) NAMING CYLIC AMINE
-e in cycloalkane name is changed to -amine
cyclohexane= cyclohexanamine
amino group is assumed to be on C1
5) NAMING AROMATIC AMINE
aromatic amine have an amine group (-NH2) attached directly to the aromatic ring.
aromatic amines known as arylamines
compounds with 2 -NH2 groups are named by adding the suffix 'diamine' to the name of the corresponding alkane or aromatic compounds
6) PREPARATION OF AMINES
A) Reduction of Halides
i) Reduction of Halides using Ammonia
R is any alkyl group attached to X (any halogen Cl, Br)
Alkyl Halides + Ammonia (+SN2) =Ammonium Salt (+NH3) = primary amine+ ammonium ion
ii) Reduction of Halides using Primary Amines
Alkyl Halides + Primary Amine (+SN2)=Ammonium Salt (+RNH2)= secondary amine + R+NH3
iii) Reduction of Halides using Secondary Amines
Alkyl Halides + Secondary Amine (+R2NH)= Ammonium Salt (+R2NH)= tertiary amine+ R2+NH2
iv) Reduction of Halides using Tertiary Amines
Alkyl Halides + R3N (+SN2)= Quartenary Ammonium Salt
B) Reduction of other ( Nitrogen-Containing Functional Groups
i) Nitro Compound
Nitro groups are reduced to primary amines using a variety of reducing agents
Example: H2/ Pd, h2/Pt, H2/Ni, Fe/HCl, Sn/HCl, LiAlH4, NaBH4
RNO2 (nitro group) + reducing agent = RNH2(primary amine)
ii) Nitriles
nitriles + (LiAlH4/H20)= 1 amine
Two-step method to convert an alkyl halide to a primary amine with one more carbon atom.
new bond is bonding with nitriles . After reaction with LiAlH4/ H20 and primary amine
iii) Primary, Secondary OR Tertiary amides
LiAlH3 is a good leaving group, so it must kick out.The ptoducts are imminium ion and it react with H-AlH3 and amine was produced.
C) Reductive amination of aldehydes and ketones
Reductive amination is a two-step method that converts aldehydes or ketones into primary,secondary or tertiary amines.
7) REACTION OF AMINES
A) Hoffman Elimination
amine = alkene
N & NH2 will be removed and double bond will be formed.The products are Agl + N(CH3)3 + H20
B) Formation of Amides
Primary & secondary amines + arcyl chlorides and acid anhydrides= amides
NH3= ammonium , products = 1 amide +HCl
Cl will be removed and replaced by NH2. One H from NH3 will bond with Cl and HCl will be formed.
RNH2= 1 amine, products = 2 amide + HCl
Cl will be removed and RNH will be replaced. One H from RNH2 bonded with cl and HCl will be formed.
R2NH= 2 amine , products= 3 amide + Hcl
Cl will be removed and replaced by R2NH. One H from R2NH bonded with Cl and HCl will be formed.
C)Formation of Quaternary Ammonium Salts
Quaternary= N is bonded with 4 different alkyl group, Salt is because there have anion and kation cas.
D) Uses of Amines
Azo dyes
Medicines-analgesic function as pain killer
Tertamethyl ammonium iodide is used in the disindection of drinking water
Pest control
Fertilizer
Vitamins