3.3.11 Amines Flashcards

1
Q

What does aliphatic mean?

A

A straight chain compound with no rings

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2
Q

What is the process with mechanisms for the synthesis of amines?

A

See card

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3
Q

What compounds are used to make amides?

A

Acyl chlorides, carboxylic acids and alcohols

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4
Q

How are polyamides produced from acyl chlorides?

A

The compound will have two acyl chloride groups on either side
The chlorine atom is replaced by NH2 - R - NH2
One of the hydrogens connected to the nitrogen is then removed and reacts with chlorine to form HCl
This happens on both sides to form a long polymer chain

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5
Q

Why are carboxylic acids used to make polyamides?

A

They produce water as a biproduct instead of HCl

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6
Q

What is the shape of ammonia?

A
H
|
N - H
|
H
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7
Q

What is the shape of a primary amine?

A
H
|
N - H
|
R
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8
Q

What is the shape of a secondary amine?

A
H
|
N - R'
|
R
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9
Q

What is the shape of a tertiary amine?

A
R"
|
N - R'
|
R
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10
Q

What is the general formula of primary amines?

A

RNH2 where the R is an aryl or alkyl group

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11
Q

What intermolecular forces are present between amines?

A

Hydrogen bonds using their NH2 groups
The hydrogen bonds are not as strong as in alcohols
This makes them soluble in water

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12
Q

What can the lone pair in an amine be used to form a bond with?

A

A H+ ion when the amine is acting as a base

An electron-deficient carbon atom when the amine is acting as a nucleophile

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13
Q

Why are amines considered as bases?

A

Amines can accept a proton so they are Bronsted-Lowry bases

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14
Q

What does an arrow on a bond signify?

A

The inductive effect
This is caused by groups releasing electrons towards the electron deficient group
This increases the electron density which makes it a better electron pair donor

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15
Q

How are primary aliphatic amines produced?

A

When halogenoalkanes are reacted with ammonia

This is nucleophilic substitution by the halide ion NH2

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16
Q

How can phenylamine be produced?

A

Benzene is reacted with a mixture of concentrated nitric and sulfuric acids which produces nitrobenzene
Nitrobenzene is reduced to phenylamine using tin and hydrochloric acid as the reducing agent
C6 H5 NO2 + 6 [H] = C6 H5 NH2 + 2H2O

17
Q

What is a phenyl group?

A

Cyclohexane with three double bonds connected to an R group

18
Q

What is the reaction mechanism for the formation of an amide?

A

See card

19
Q

How are primary amines produced via the reduction of nitriles?

A

Nitriles contain the functional group - CN
They can be reduced to primary amines with a nickel / hydrogen catalyst
R - CN + 2H2 = R - CH2NH2

20
Q

How is a nitrile formed from a halogenoalkane?

A

Halogenoalkanes react with cyanide ions is aqueous ethanol
The cyanide ion replaces the halide ion by nucleophilic substitution to form a nitrile
RBr + CN- = R - CN + Br-