Amines - Nitrogen Compounds Flashcards

(38 cards)

1
Q

What is an acid?

A

Releases H+

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2
Q

What is base?

A

A compound that neutralises an acid, by accepting H+, to form a salt

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3
Q

What is a salt?

A

Product of a reaction in which H+ from the acid is replaced by a metal or ammonium ion

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4
Q

What does a compound have to have to be a base?

A

Has to have a lone pair or negative charge

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5
Q

What are examples of bases?

A

Metal oxide
Metal carbonate
Metal hydroxide
Ammonia - accepts H+ to form NH4+

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6
Q

Can amines behave as bases?

A

YES

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7
Q

Why can ammonia behave as a base?

A

Lone pair on the N

So can accept H+ to form NH4+

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8
Q

What do you form when you add H+ to ethylamine?

A

Ethylammonium ion

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9
Q

What product is formed from CH3CH2NH2 + HCl?

A

CH3CH2NH3+Cl-

Ethylammonium chloride

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10
Q

What product is formed from CH3CH2CH2NH2 + H2SO4?

A

(CH3CH2CH2NH3)2SO4

Dipropylammonium sulphate

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11
Q

What product is formed from CH3CH2CH2NH2 + H3PO4?

A

(CH3CH2CH2NH3)3PO4

Tripropylammonium phosphate

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12
Q

What does the strength of a base depend on?

A

How available the nitrogen’s lone pairs are

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13
Q

What does it mean if a lone pair is more available?

A

Electron density = higher = stronger the base

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14
Q

Order ammonia, amine and phenylamine from weakest to strongest base

A

Phenylamine
Ammonia
Amine

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15
Q

Why is phenylamine the weakest base?

A

Benzene ring pulls electrons towards delocalised ring
Electron density increases at ring
So L.P less available

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16
Q

Why is ammonia the middle base?

A

Doesn’t have an aromatic ring to pull L.P away

Doesn’t have an alkyl group to pull L.P towards

17
Q

Why is amine the strongest base?

A

Alky group pushes electrons towards N
Electron density increases at N
So L.P more available

18
Q

What is the first step of forming a primary aliphatic amine?

A

Haloalkane + NH3 —-> ammonium salt

19
Q

What is formed when 1-chloroethane + NH3?

A

CH3CH2NH3Cl

Ethylammonium chloride

20
Q

What is the second step of forming a primary aliphatic amine?

A

Ammonium salt + aqueous alkali —-> primary amine + NaCl + H2O

21
Q

What is formed when Ethylammonium chloride + NaOH?

A

CH3CH2NH2 + NaCl + H2O

Ethylamine

22
Q

What are the conditions needed for forming a primary aliphatic amine?

A

Excess NH3

Ethanol as a solvent

23
Q

Why do you need excess NH3 when forming a primary aliphatic amine?

A

Don’t want further substitution

24
Q

Why do you need ethanol when forming a primary aliphatic amine?

A

To prevent substitution of haloalkane by water to make an alcohol

25
How is ethanol used when forming a primary aliphatic amine?
NH3 dissolved in ethanol | Ethanolic ammonia
26
What is the first step of forming a secondary aliphatic amine?
Primary amine + haloalkane ----> ammonium salt
27
What is formed when ethylamine + 1-chloroethane?
(CH3CH2)2NH2+Cl- | Diethylammonium chloride
28
What is the second step of forming a secondary aliphatic amine?
Ammonium salt + NaOH ----> secondary amine + NaCl + H2O
29
What is formed when diethylammonium chloride + NaOH?
(CH3CH2)2NH + NaCl + H2O | N,N diethylamine
30
What is the first step of forming a tertiary aliphatic amine?
Secondary amine + haloalkane ----> ammonium salt
31
What is formed when N,N diethylamine + | 1-chloroethane?
(CH3CH2)3NH+Cl- | Triethylammonium chloride
32
What is the second step of forming a tertiary aliphatic amine?
Ammonium salt + NaOH ----> tertiary amine + NaCl + H2O
33
What is formed when triethylammonium chloride + NaOH?
(CH3CH2)3N + NaCl + H2O | Triethylamine
34
What is the first step of forming aromatic amines?
Nitrobenzene + 7[H] ----> Phenylammonium chloride | + 2H2O
35
What is the second step when forming aromatic amines?
Phenylammonium chloride + NaOH ----> Phenylamine + H2O
36
What conditions are needed for the first step of forming an aromatic amine?
Conc HCl Sn REFLUX
37
What conditions are needed for the second step of forming an aromatic amine?
NaOH in excess
38
What is the overall equation for forming an aromatic amine?
Nitrobenzene + 6[H] ----> Phenylamine + 2H2O