Amines Flashcards

1
Q

Primary amine

A

The nitrogen atom is attached to one carbon chain

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2
Q

how are amines named if the -NH2 is on carbon 1

A

alkylamine

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3
Q

how are amines names if the -NH2 is on any carbon besides carbon 1

A

-aminoalkane

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4
Q

How do you name compounds where two or more different groups are attached to a nitrogen atom

A

N-substituted derivative of the larger group

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5
Q

Why do amines have a high boiling temperature

A

There are hydrogen bonds between molecules of an amine as they have a polar N-H bond

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6
Q

Why does ethylamine dissolve in water

A

It can form hydrogen bonds with water molecules because is has a polar N-H bond

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7
Q

Why are amines less soluble in water as the relative molecular mass increases

A

As the molar mass increases, the non-polar hydrocarbon chain which is insoluble becomes larger. Therefore solubility decreases

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8
Q

What are the two ways primary aliphatic amines are prepared

A

By the reaction of ammonia with halogenoalkanes and by the reduction of nitriles

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9
Q

What are the reagents, conditions and the mechanism for the reaction of ammonia with halogenoalkanes

A

Reagent - excess ammonia dissolved in ethanol
Conditions - Heat under pressure in a sealed tube
Mechanism - Nucleophilic substitution

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10
Q

Why is ammonia dissolved in ethanol when reacting with a halogenoalkane

A

To prevent halogenoalkane reacting with water as water is a nucleophile.
Alcohol is also formed

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11
Q

Why is excess ammonia used when reacting with a halogenoalkane

A

To prevent further substitution of the amine group to form secondary and tertiary amines

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12
Q

Reagents and conditions needed for the reduction of nitriles to amines

A

Reagents : H2/Ni
Conditions : High temperature, high pressure

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13
Q

What is the equation for the reduction of propanenitrile to propylamine

A

CH3CH2CN + 2H2 = CH3CH2CH2NH2

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14
Q

How are aromatic amines prepared

A

By the reduction of nitro compounds such as nitrobenzene

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15
Q

Reagents, conditions and reaction for nitrobenzene into phenylamine

A

Reagents: Sn/HCL
Conditions : Heat under reflux
Reaction : Reduction

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16
Q

What are aromatic amines used in

A

The preparation of dyes

17
Q

What does ammonia act as in the first step of nucleophilic substitution

A

A nucleophile as it donates a lone pair of electrons

18
Q

What does ammonia act as in the second step of nucleophilic substitution

A

A base as it reacts with a H+ ion to form an NH4+ ion

19
Q

Equation for the reduction of nitrobenzene into phenylamine

A

C6H5NO2 + 6[H] = C6H5NH2 + 2H2O

20
Q

Are amines basic or acidic

A

Amines are weak bases as the lone pair of electrons on the N atom allows an amine to act as a base

21
Q

What is the order of base strength of amines

A

Aromatic amines < ammonia < primary amines < tertiary amines < Secondary amines

22
Q

Why are primary aliphatic amines stronger bases than ammonia

A

The alkyl groups are electron releasing and push electrons towards the nitrogen atom, making the lone pair of electrons on the nitrogen more readily available. (CAN SAY POSITIVE INDUCTIVE EFFECT)

23
Q

Why are secondary amines stronger bases than primary amines

A

Secondary amines have more alkyl groups therefore more electron density pushed onto the N atom and the positive inductive effect is greater. The lone pair of electrons on the N atom is more readily available.

24
Q

Why are primary aromatic amines such as phenylamine such weak bases

A

The lone pair of electrons on the nitrogen delocalise into the benzene ring so the lone pair on the N atom is less readily available.

25
Q

How do amines react with acids

A

They form ammonium salts

26
Q

What happens if NaOH is added to an ammonium salt

A

Converts back to the amine

27
Q

Why are ammonium salts soluble

A

They are ionic compounds

28
Q

How are secondary amines formed

A

The primary amine reacts with the halogenoalkane as it has a lone pair of electrons on the nitrogen.

THIS TREND REPEATS TO FORM TERTIARY AMINES AND QUATERNARY SALTS (only first step of nuc subs happens when forming quaternary ammonium salts)

29
Q

Uses of quaternary ammonium salts

A

cationic surfactants
fabric softeners
conditioners

30
Q

Aliphatic amine/ phenylamine + acyl chloride

A

N-alkyl…amide + HCL

31
Q

Explain why 3-aminopentane is a stronger base than ammonia

A

in 3-aminopentane the lone pair on N more available because of alkyl electron pushing / inductive effect

32
Q

Explain the difference in base strength between amines E (C6H5NH2), F (C6H5CH2CH2NH2) and amine G (C6H5NHCH2CH3)

A

Strength depends on availability of the lone pair on the N

In E : N is next to the ring so the lone pair id delocalised into the ring and is less available.

in F/G : The N is next to alkyl groups so positive inductive effect/electrons pushed to N and lone pair more available.

E<G<F