3.11 - Amines Flashcards

1
Q

Define: Basicity

A

Ability of a Substance to act as a Base

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2
Q

Name of Mechanism: Reaction of 1° Amine & Acid Anhydride

A

Nucleophilic Addition-Elimination

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3
Q

Name of Mechanism: Reaction of Ammonia & Acyl Chloride

A

Nucleophilic Addition-Elimination

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4
Q

How can the Amine be Reformed from its Alkylammonium Salt?

A

Adding an Alkali

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5
Q

Amines dissolve in Acid to form ____ ?

A

Corresponding Alkylammonium Salt

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6
Q

In excess ____, 4° ammonium salt is produced

RX |> RNH₂ |> R₂NH |> R₃N |> R₄N⁺X⁻

A

Halogenoalkane, RX

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7
Q

Organic Product: Reaction of 1° Amine & Acid Anhydride

A

2° Amide & Carboxylic Acid

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8
Q

Why is an Excess of Amine used in reactions of Amines w/ Halogenoalkane?

A

Prevent Further Substitution

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9
Q

Unless an Excess of Amine is used ____ reactions can occur with 1° & 2° Amines until a ____ is produced?

A

Further Substitution

Quaternary Ammonium Salt

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10
Q

Name of Mechanism: Reaction of Ammonia & Acid Anhydride

A

Nucleophilic Addition-Elimination

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11
Q

Name of Mechanism: Reaction of Ammonia & Halogenoalkane

A

Nucleophilic Substitution

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12
Q

Name of Mechanism: Reaction of Amine & Acyl Chloride

A

Nucleophilic Addition-Elimination

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13
Q

Organic Product: Reaction of 1° Amine & Acyl Chloride

A

2° Amide

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14
Q

Why are Ammonia & Amines Weak Bases?

A

Lone pair of Electrons on Nitrogen atom can Accept a Proton

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15
Q

Ammonia & Amines are ____ Bases?

A

Weak

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16
Q

Name of Mechanism: Reaction of 3° Amine & Halogenoalkane

A

Nucleophilic Substitution

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17
Q

Organic Product: Reaction of 3° Amine & Halogenoalkane

A

Quaternary Ammonium Salt

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18
Q

Organic Product: Reaction of Ammonia & Acid Anhydride

A

Amide & Carboxylic Acid

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19
Q

Name of Mechanism: Reaction of 2° Amine & Halogenoalkane

A

Nucleophilic Substitution

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20
Q

Functional Group: Amide

A

-C(=O)-N-

21
Q

Organic Product: Reaction of Ammonia & Acyl Chloride

A

Amide

22
Q

Define: Base

A

A substance that accepts H⁺ ions

23
Q

Define: Nucleophile

A

Electron Pair Donor

24
Q

Name of Mechanism: Reaction of 1° Amine & Halogenoalkane

A

Nucleophilic Substitution

25
Q

Quaternary Ammonium ions have long ____ hydrocarbon chains which are ____ in water

A

Non-Polar

Not Soluble

26
Q

Type of Reaction: Nitriles to Primary Aliphatic Amines

A

Reduction

27
Q

Why are Aromatic Amines Weaker Bases than Ammonia?

A

Lone Pair on N is less able to accept H⁺ as it is Delocalised into the Benzene ring (e⁻ density on N decreases)

28
Q

Quaternary Ammonium Ions are ____ charged (____)

The Ionic region is ____ in water

A

Positively
Cationic
Soluble

29
Q

Why are 1° Aliphatic Amines Stronger Bases than Ammonia

A

Lone Pair on N is more able to accept H⁺ as it is due to Positive Inductive Effect (e⁻ density on N increases)

30
Q

Name of Mechanism: Halogenoalkanes to Primary Aliphatic Amines

A

Nucleophilic Substitution

31
Q

General Equation: Halogenoalkanes to Primary Aliphatic Amines

A

R-X + 2NH₃ |> R-NH₂ + NH₄X

32
Q

Type of Reaction: Nitrobenzenes to Aromatic Amines

A

Reduction

33
Q

Conditions: Nitrobenzenes to Aromatic Amines

A

Reflux

34
Q

Reagents: Nitrobenzenes to Aromatic Amines

A

Tin & conc. HCl

35
Q

Uses of Aromatic Amines?

A

Pharmaceuticals & Dyes

36
Q

General Equation: Reaction of Ammonia & Acid Anhydride

A

R-C(=O)-O-C(=O)-R + NH₃ |> R-C(=O)-NH₂ + R-C(=O)-OH

37
Q

General Equation: Reaction of 1° Amine & Acid Anhydride

A

R-C(=O)-O-C(=O)-R + R’NH₂ |> R-C(=O)-NH-R + R-C(=O)-OH

38
Q

General Equation: Nitriles to Primary Aliphatic Amines

A

R-C≡N + 2H₂ |> R-CH₂NH₂

39
Q

General Equation: Reaction of 2° Amine & Halogenoalkane

A

2RR’NH + R’‘X |> R’‘RR’N + RR’NH₂X

40
Q

General Equation: Reaction of 1° Amine & Acyl Chloride

A

R-C(=O)-Cl + 2R’NH₂ |> R-C(=O)-NH-R’ + R’NH₃Cl

41
Q

General Equation: Reaction of Ammonia & Halogenoalkane

A

RX + 2NH₃ |> RNH₂ + NH₄X

42
Q

General Equation: Reaction of 3° Amine & Halogenoalkane

A

R’'’X + RR’R’‘N |> R’'’R’‘R’RN⁺ + X⁻

43
Q

General Equation: Reaction of 1° Amine & Halogenoalkane

A

RX + 2R’NH₂ |> RR’NH + R’NH₃X

44
Q

General Equation: Reaction of Ammonia & Acyl Chloride

A

R-C(=O)-Cl + 2NH₃ |> R-C(=O)NH₂ + NH₄Cl

45
Q

Uses of Quaternary Ammonium Salts?

A

Cationic Surfactants in Detergents & Softeners

46
Q

What can be used to Prevent Further Substitution of Amines w/ Halogenoalkanes?

A

Excess of Amine

47
Q

Order of Basicity of Amines is?

A

3° > 2° > 1° > ammonia > aromatic amines

48
Q

Reagents & Conditions: Nitriles to Primary Aliphatic Amines

A

H₂ & Ni Catalyst

49
Q

Define: Surfactants

A

Compounds w/ regions which are Partly Soluble in Water & Partly Insoluble