3.11 - Amines Flashcards
Define: Basicity
Ability of a Substance to act as a Base
Name of Mechanism: Reaction of 1° Amine & Acid Anhydride
Nucleophilic Addition-Elimination
Name of Mechanism: Reaction of Ammonia & Acyl Chloride
Nucleophilic Addition-Elimination
How can the Amine be Reformed from its Alkylammonium Salt?
Adding an Alkali
Amines dissolve in Acid to form ____ ?
Corresponding Alkylammonium Salt
In excess ____, 4° ammonium salt is produced
RX |> RNH₂ |> R₂NH |> R₃N |> R₄N⁺X⁻
Halogenoalkane, RX
Organic Product: Reaction of 1° Amine & Acid Anhydride
2° Amide & Carboxylic Acid
Why is an Excess of Amine used in reactions of Amines w/ Halogenoalkane?
Prevent Further Substitution
Unless an Excess of Amine is used ____ reactions can occur with 1° & 2° Amines until a ____ is produced?
Further Substitution
Quaternary Ammonium Salt
Name of Mechanism: Reaction of Ammonia & Acid Anhydride
Nucleophilic Addition-Elimination
Name of Mechanism: Reaction of Ammonia & Halogenoalkane
Nucleophilic Substitution
Name of Mechanism: Reaction of Amine & Acyl Chloride
Nucleophilic Addition-Elimination
Organic Product: Reaction of 1° Amine & Acyl Chloride
2° Amide
Why are Ammonia & Amines Weak Bases?
Lone pair of Electrons on Nitrogen atom can Accept a Proton
Ammonia & Amines are ____ Bases?
Weak
Name of Mechanism: Reaction of 3° Amine & Halogenoalkane
Nucleophilic Substitution
Organic Product: Reaction of 3° Amine & Halogenoalkane
Quaternary Ammonium Salt
Organic Product: Reaction of Ammonia & Acid Anhydride
Amide & Carboxylic Acid
Name of Mechanism: Reaction of 2° Amine & Halogenoalkane
Nucleophilic Substitution
Functional Group: Amide
-C(=O)-N-
Organic Product: Reaction of Ammonia & Acyl Chloride
Amide
Define: Base
A substance that accepts H⁺ ions
Define: Nucleophile
Electron Pair Donor
Name of Mechanism: Reaction of 1° Amine & Halogenoalkane
Nucleophilic Substitution
Quaternary Ammonium ions have long ____ hydrocarbon chains which are ____ in water
Non-Polar
Not Soluble
Type of Reaction: Nitriles to Primary Aliphatic Amines
Reduction
Why are Aromatic Amines Weaker Bases than Ammonia?
Lone Pair on N is less able to accept H⁺ as it is Delocalised into the Benzene ring (e⁻ density on N decreases)
Quaternary Ammonium Ions are ____ charged (____)
The Ionic region is ____ in water
Positively
Cationic
Soluble
Why are 1° Aliphatic Amines Stronger Bases than Ammonia
Lone Pair on N is more able to accept H⁺ as it is due to Positive Inductive Effect (e⁻ density on N increases)
Name of Mechanism: Halogenoalkanes to Primary Aliphatic Amines
Nucleophilic Substitution
General Equation: Halogenoalkanes to Primary Aliphatic Amines
R-X + 2NH₃ |> R-NH₂ + NH₄X
Type of Reaction: Nitrobenzenes to Aromatic Amines
Reduction
Conditions: Nitrobenzenes to Aromatic Amines
Reflux
Reagents: Nitrobenzenes to Aromatic Amines
Tin & conc. HCl
Uses of Aromatic Amines?
Pharmaceuticals & Dyes
General Equation: Reaction of Ammonia & Acid Anhydride
R-C(=O)-O-C(=O)-R + NH₃ |> R-C(=O)-NH₂ + R-C(=O)-OH
General Equation: Reaction of 1° Amine & Acid Anhydride
R-C(=O)-O-C(=O)-R + R’NH₂ |> R-C(=O)-NH-R + R-C(=O)-OH
General Equation: Nitriles to Primary Aliphatic Amines
R-C≡N + 2H₂ |> R-CH₂NH₂
General Equation: Reaction of 2° Amine & Halogenoalkane
2RR’NH + R’‘X |> R’‘RR’N + RR’NH₂X
General Equation: Reaction of 1° Amine & Acyl Chloride
R-C(=O)-Cl + 2R’NH₂ |> R-C(=O)-NH-R’ + R’NH₃Cl
General Equation: Reaction of Ammonia & Halogenoalkane
RX + 2NH₃ |> RNH₂ + NH₄X
General Equation: Reaction of 3° Amine & Halogenoalkane
R’'’X + RR’R’‘N |> R’'’R’‘R’RN⁺ + X⁻
General Equation: Reaction of 1° Amine & Halogenoalkane
RX + 2R’NH₂ |> RR’NH + R’NH₃X
General Equation: Reaction of Ammonia & Acyl Chloride
R-C(=O)-Cl + 2NH₃ |> R-C(=O)NH₂ + NH₄Cl
Uses of Quaternary Ammonium Salts?
Cationic Surfactants in Detergents & Softeners
What can be used to Prevent Further Substitution of Amines w/ Halogenoalkanes?
Excess of Amine
Order of Basicity of Amines is?
3° > 2° > 1° > ammonia > aromatic amines
Reagents & Conditions: Nitriles to Primary Aliphatic Amines
H₂ & Ni Catalyst
Define: Surfactants
Compounds w/ regions which are Partly Soluble in Water & Partly Insoluble