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Organic Chemistry > Amines > Flashcards

Amines Flashcards

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1
Q

Why can primary amines act as a base?

What else can it act as?

A

The N has a lone pair which can accept a proton

A nucleophile as this lone pair can donate to a delta positive C

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2
Q

Why can secondary amines act as a base?

What else can it act as?

A

The lone pair on N can accept a proton

A nucleophile as the lone pair can donate to a delta positive C

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3
Q

Why can tertiary amines act as a base?

What else can it act as?

A

The N has a lone pair which can accept a proton

A nucleophile as this lone pair can donate to a delta positive C

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4
Q

Can quaternary ammonium salts act as a base?

A

Nope

There is no lone pair on the N so it does not react

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5
Q

2 ways to prepare an amine?

A

Nucleophilic substitution

Catalytic hydrogenation

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6
Q

What is the equation for the reaction of bromoethane and an excess of NH3?

Why is an excess used?

What is the mechanism?

A

CH3CH2Br + 2 NH3 —-> CH3CH2NH2 + NH4Br

To avoid further substitution

Nucleophilic substitution

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7
Q

What is the disadvantage of forming amines via nucleophilic substitution?

A

A low yield of primary amine is produced

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8
Q

Why is a low yield of primary amine formed for nucleophilic substitution?

A

A mixture of amine products formed due to product also acting as a nucleophile

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9
Q

What is another name for preparing an amine using catalytic hydrogenation?

A

Reduction of a nitrile

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10
Q

What are the two steps for the reduction of a nitrile?

A

RBr + CN- —-> RCN + Br-

RCN + 2H2 ——> RCH2NH2

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11
Q

Overall equation for reduction of a nitrile

A

RCN + 2H2 ——> RCH2NH2

Nickel catalyst!

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12
Q

What is the advantage of reducing a nitrile

Why

A

High yield of product formed

Product does not react with nitrile

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13
Q

How to form an aromatic amine

A

Reduction of nitrobenzene using Sn/ HCl

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14
Q

What is the equation for the reduction of nitrobenzene

A

Nitrobenzene + 6[H] —-> amino benzene + 2H2O

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15
Q

What salt is produced from the reduction of nitrobenzene

Why is this formed?

A

C6H5NH3+Cl-

Reaction is carried out using HCl so amino benzene reacts with HCl

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16
Q

What is used to liberate the free amine after the reduction of nitrobenzene

What is the equation?

A

NaOH

RNH3+Cl- + NaOH —-> amino benzene + H2O + NaCl

17
Q

Are amines strong bases?

Why?

A

No they’re weak bases

They partially dissociate in water

18
Q

What happens when ammonia acts as a base?

A

The lone pair on N is donated to accept a proton

19
Q

What is the equation for ammonia and H+

A

NH3 + H+ —-> NH4+

20
Q

What does the strength of amines as. bases depend on?

A

The availability of the lone pair

21
Q

Aromatic amines are stronger bases than aliphatic amines. true or false?

A

False

22
Q

Why Are aromatic amines weaker bases?

A

The lone pair on N overlaps with the delocalised ring (negative inductive effect)

Making lone pair less available

23
Q

Why are aliphatic amines strong bases?

A

R group pushes e- towards lone pair on N (positive inductive effect)

Making lone pair on N more available

24
Q

How does chain length affect the positive inductive effect?

A

Effect increases/ is stronger with increasing chain length

25
Q

C chains release e-

True or false

What is this effect

A

Positive inductive effect

26
Q

When negative inductive effect occur?

A

For electronegativity and for benzene ring

27
Q

Describe 2 kinds of negative inductive effect

A

Benzene ring overlaps with e-

Electronegative atoms withdraw e-

28
Q

What are amines used for?

A

Making nylon/ drugs

29
Q

What are quaternary ammonium salts used for?

A

Hair products

30
Q

When are polymers formed?

A

When monomers join to form a long chain molecule

31
Q

What mechanism is usually used in addition polymerisation?

A

Free radical

32
Q

Explain why polyalkenes are non-biodegradable

A

Strong C-C bonds are non-polar / there are no polar bonds

33
Q

How to form a poly(Ester)

A

Di-carboxylic acid + diol

34
Q

What are condensation polymers?

A

Molecules formed from monomers with functional groups at both ends of the molecule

Organic Chemistry (12 decks)

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