I completed chemistry A-Level in one year, teaching most of the course to myself, I found it easiest like this as all the information from the textbook is streamlined and in one place. Comparing all past mark schemes I wrote the summaries using words and highlighting phrases you must use in the exa...
Amines
28.1 Introduction to amines: Reduction of nitriles makes a primary amine-
1. Nucleophilic substitution with a cyanide ion in
Amines are derivatives of ammonia where H atoms are aqueous ethanol conditions forming a nitrile.
replaced by hydrocarbon chains, the amount of chains 2. Nitrile can be reduced using hydrogen or nickel
depends if the amine is primary, secondary or tertiary. catalyst.
Making phenylamine-
1. Benzene reacts with nitric acid and concentrated
sulphuric acid to from nitrobenzene
Primary Secondary Tertiary 2. Nitrobenzene is reduced reduced by tin and HCL
NH3
(forms H)
• very reactive, due to the Electronegativity difference 3. C6H5NO2 + 6[H] —> C6H5NH2 + 2H2O
between N and H, allows it to H bond. N atom has 4. Also forms a salt with HCL and so NaOH can be
the lone pair of electrons added to remove the amine.
• High melting point but less than alcohol, N is less 5. C6H5NH3Cl + NaOH —> C6H5NH2 + H2O +NaCl
electronegative than O and so the bonds are weaker
• Solubility depends on the length of the hydrocarbon Amides are formed through nucleophilic addition-
chain elimination reactions with an amine and acyl chlorides/
• base, the lone pair can accept a H+ ion acid anhydrides.
• Can act as a nucleophile
Naming take the alkyl group and add the suffix
-amine if there’s multiple of the same alkyl chains it
becomes di,tri,tetra
28.2 The properties of amines as bases:
Amines will accept an H+ion as a Brønsted-Lowry
Common Exam questions:
base. Will react with acids in neutralisation reactions
and produce salts.
“Would this amine be primary, secondary or tertiary”
Inductive effect, changes the strength of the base. Alkyl
“Explain the positive inductive effect”
groups release electrons and so the N atom becomes more
negatively charged, so it’s a better electron pair donator.
“Why are some mines better bases than others?”
The more alkyl groups there are the stronger the ability
of the amine to act as a base, tertiary amines are not
“Draw the mechanism for a nucleophile substitution
good bases as they are less soluble in solution.
reaction with ammonia/cyanide”
“What conditions would you need to reduce a nitrile/to
28.3 Amines as nucleophiles and their synthesis: form a amine from a nitrile?”
Reactions with halogenoalkanes “What’s the process for producing phenylamine, what
conditions are needed?”
1. The amine’s lone pair of electrons will be attracted to
the slightly positive carbon atom, forming a dative
bond
2. Carbon has too many bonds and so the weakest
bond breaks C-X
3. Positive charge on the ammonia and so the N-H
bond breaks, producing an amine.
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