Amines Flashcards

1
Q

Describe the structure of an amine.

A

Derived from ammonia molecules and all contain a nitrogen atom where hydrogens are replaced with an organic group e.g. an alkyl group.

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2
Q

Describe the structure of a primary amine.

A

One alkyl group replaces hydrogen.
2 hydrogens and 1 alkyl group

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3
Q

Describe the structure of secondary amines.

A

2 alkyl groups replace hydrogens;
2 alkyl groups and 1 hydrogen.

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4
Q

Describe the structure of tertiary amines.

A

Three alkyl groups replace the three hydrogens.

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5
Q

Describe the structure of a quaternary ion.

A

4 alkyl groups surround the nitrogen therefore it has a positive charge.

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6
Q

How can primary aliphatic amines be prepared?

A

By the reaction of ammonia (NH3) with halogenoalkanes
AND
The reduction of nitriles.

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7
Q

What is an aromatic amine?

A

A primary amine.

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8
Q

What is a cationic surfactant?

A

Quaternary ammonia salts that have a long hydrocarbon ‘tail’;
Quaternary salts are made from a positive head group and is attracted to negative ions.

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9
Q

State some of the uses of cationic surfactants.

A

Used to make cleaning products such as shampoo, laundry detergents and washing up liquids.

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10
Q

How do cationic surfactants work?

A

The non-polar tail is attracted to the oil/grease;
The polar head will be attracted to the water;
This allows the water and oil to mix and removes grease from clothing, skin and dishes.

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11
Q

How can amines act as bases?

A

Amines have a lone pair of electrons that allows them to accept a proton.

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12
Q

How does the proton bind to the amine?

A

Via a dative covalent bond;
Both electrons in the bond originate from the lone pair on the nitrogen.

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13
Q

What is the strength of the base dependent on?

A

The availability of the lone pair of electrons on the nitrogen;
The higher the electron density the more readily available the electrons are.

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14
Q

What is electron density on the nitrogen dependent on?

A

The type of group attached to the nitrogen.

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15
Q

State the order of base strength from weakest to strongest.

A

Aromatic amines> ammonia > primary aliphatic amines

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16
Q

Explain why benzene is the weakest base.

A

Benzene is an electron withdrawing group so it pulls electrons away from the nitrogen into the ring structure;
Electron density at nitrogen reduces so the lone pair availability is reduced and aromatic amines are less basic.

17
Q

Explain why primary aliphatic amines are the strongest base.

A

Alkyl groups are electron pushing groups so they push electrons towards nitrogen;
Electron density at nitrogen increases so lone pair availability increases and primary aliphatic amines are more basic.

18
Q

State another property on amines other than as bases.

A

They are nucleophiles.

19
Q

State the mechanism when reacting halogenoalkane and ammonia.
State the reagents and conditions.

A

Mechanism: Nucleophilic substitution
Reagent: Ammonia in EXCESS
Conditions: Heat

20
Q

Draw the mechanism when chloroethane reacts with excess ammonia.

A
  1. First curly arrow from lone pair on ammonia to delta positive carbon.
  2. Second curly around from C-CL bond to delta negative chlorine.
    EXCESS AMMONIA SO:
  3. Third curly arrow from lone pair on ammonia to H on positive N
  4. Fourth curly arrow from N-H bond to positive N.
21
Q

What is the downside of reacting halogenoalkanes and ammonia?

A

The reaction also produces secondary, tertiary and quaternary salts so we have an impure product;
This occurs as primary amine still have a lone pair of electrons on the nitrogen so also act as a nucleophile;
The amine can react with any remaining halogenoalkane to produce secondary amines, then react further to make tertiary and quaternary salts.

22
Q

State the reagents and conditions when reducing nitriles to produce amines.

A

Reagent - H2 (hydrogen gas)
Conditions - Ni (nickel catalyst), hight temp and pressure.

Reagent - LiAlH4 (strong reducing reagent) and dilute acid

23
Q

What is the reaction of reducing nitriles called when using H2 gas and a nickel catalyst?

A

Catalytic Hydrogenation

24
Q

What are advantages of producing amines from reducing nitriles using hydrogen gas and nickel catalyst?

A
  1. Cheapest way to make primary amines in industry.
  2. Only produces primary amines so a pure product is made.
25
Q

What is the reaction called when we use LiAlH4 and dilute acid to reduce nitriles?

A

Reduction reaction

26
Q

What are disadvantages of the reduction reaction?

A

More expensive than catalytic hydrogenation and LiAlH4 is more expensive than H2 gas and a nickel catalyst so it is not used in industry.

27
Q

What is the reducing agent in the reduction reaction to make amines from nitriles dissolved in?

A

A non-aqueous solvent such as dry ether.

28
Q

How are aromatic amines produced?

A

Made by reducing nitrocompounds such as nitrobenzene.

29
Q

What are aromatic amines used for?

A

To make dyes and pharmaceuticals.

30
Q

Describe the steps to make aromatic amines from nitrobenzene.

A

Step 1 - heat nitrobenzene under reflux with concentrated HCL and tin to form a salt.
Step 2 - The salt produced is reacted with an alkali such as NaOH to produce an aromatic amine.