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Chemistry - Module 6 > 27- Amines, Amino Acids And Polymers > Flashcards

27- Amines, Amino Acids And Polymers Flashcards

1
Q

Primary amine

A

1 R group

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2
Q

Secondary amine

A

2 R groups

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3
Q

Tertiary amine

A

3 R groups

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4
Q

Ammonia

A

0 R groups

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5
Q

Characteristics of amines

A

• Pungent smell

• Physiological effects
o Amphetamine (Treats fatigue)
o Phenylephrine (Decongestant)
o Adrenaline (Stress hormone)

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6
Q

How to name a primary amine

A

• If –NH₂ group is at the end of a chain, add the suffix –amine to the end of the alkyl chain

• If it contains an amine group on any other C other than C-1 the amine is named using the prefix amino- and a number is added to indicate the position

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7
Q

Name this

A

Ethylamine

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8
Q

Name this

A

2-aminobutane

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9
Q

How to name a secondary / tertiary amine

A

• If they contain the same alkyl group, the prefixes di- or –tri are used to indicate the number of alkyl groups attached to the nitrogen

• two or more different groups are attached to a N, the compound is named as a N-substituted derivative of the larger group.

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10
Q

Name these

A
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11
Q

Name these

A
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12
Q

What do amines behave as

A

Weak bases

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13
Q

Why do they behave as weak bases

A

o Lone pair on N atom can accept a proton

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14
Q

What are amines

A

Bases

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15
Q

How to form a salt from an amine

A

• Acid + Amine -> Ammonium Salt

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16
Q

Write reaction between HCl and propylamine

A
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17
Q

Write reaction between Sulfuric acid and butylamine

A
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18
Q

What type of reaction are these

A

Neutralisation

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19
Q

Name or mechanism that prepares primary aliphatic amines

A

Nucleophilic substitution

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20
Q

Type of reaction that prepares primary aliphatic amines

A

2 step

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21
Q

How to prepare primary aliphatic amines - overall

A
  1. Salt formation
  2. Amine formation
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22
Q

Step 1 of primary amine preparation - salt formation

A

• Ammonia acts as a nucleophile as it has a lone pair of electrons on the N.

• Ammonia reacts with haloalkane to form salt

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23
Q

Step 2 of primary amine preparation - amine formation

A

• Ammonium salt reacts with sodium hydroxide

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24
Q

Conditions of primary amine formation

A
  • ethanol solvent
  • excess ammonia
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25
Q

Why ethanol solvent condition - primary amine formation

A

 Prevents substitution of haloalkane with water (to form alcohols)

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26
Q

Why excess ammonia condition - primary amine formation

A

 Reduces further substitution of the amine to form secondary and tertiary amines

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27
Q

Preparation of secondary aliphatic amines - 2 step

A
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28
Q

Preparation of tertiary aliphatic amines - 2 step

A
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29
Q

Why can we prepare secondary / tertiary amines this way

A

primary / secondary amine still contains a lone pair of electrons on the N atom, so can react further with a haloalkane and form a secondary / tertiary amine

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30
Q

Nucleophile in preparation of amines

A

Ammonia / amine

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31
Q

Preparation of aromatic amines - 2 steps overall

A

Salt formation

Amine formation

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32
Q

Preparation of aromatic amines - salt formation - conditions

A
  • Tin and conc. HCl act as a reducing agent
  • Heated under reflux
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33
Q

Preparation of aromatic amines - amine formation - conditions

A
  • Excess NaOH (aq) is added to produce the aromatic amine
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34
Q

Type of reaction for Preparation of aromatic amines

A

• Nitroarenes are reduced to form aromatic amines.

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35
Q

Wrote equation for formation of phenylamine

A
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36
Q

How many natural amino acids in body

A

20

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37
Q

Type of natural body amino acids

A

Alpha

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38
Q

What is an alpha amino acid

A

o amine is attached to the alpha C - one carbon separating two functional groups

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39
Q

Naming alpha amino acids

A

• carboxylic acid group takes priority = amine group will always be at position 2 in an α-amino acids (2-amino).

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40
Q

Name

A
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41
Q

Reactions of Amino acids - list

A

• with acids
• with alkalis
• with alcohols

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42
Q

Reaction of amino acid with acids

A

• basic -NH₂ can react with acids to form ammonium salt

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43
Q

Reaction between amino acids and acids

A

• basic -NH₂ can react with acids to form ammonium salt

44
Q

Draw reaction between alanine and HCl

45
Q

Reactions of amino acids with alkalis

A

• -COOH can react with alkalis (such as NaOH or KOH) to form salt + water.

46
Q

Draw general reaction between amino acid + NaOH

47
Q

Reaction between amino acids and alcohol + CONDITIONS

A

• -COOH can easily be esterified by heating with an alcohol in the presence of conc. H₂SO4 catalyst.

48
Q

Reaction between amino acids + alcohols are in acidic conditions - remember reaction conditions - why is this significant

A

basic amine group is protonated.

49
Q

Write draw reaction between alanine and ethanol

50
Q

How do Zwitterions form

A

the basic -NH₂ can accept a proton from the –COOH to form an ion containing both a +ve and –ve charge.

51
Q

What’s the isoelectric point

A

• pH at which the zwitterion is formed

52
Q

What’s special about the isoelectric point

A

• Each amino acid has its own unique isoelectric point.

53
Q

If pH is higher then isoelectric

A

amino acid acts as an acid, and loses a proton from -COOH

54
Q

If pH is lower than isoelectric

A

amino acid acts as a base, and accepts a proton in -NH2

55
Q

Spectrum of pH

56
Q

Properties of amino acids

A

• Bifunctional – act as acid and base

57
Q

Investigate properties of amino acids- method

A
  1. Find the melting point of glycine.
  2. Dissolve one spatula measure of glycine in 3 cm3 of distilled/deionised water. Test the pH of the solution with universal indicator paper.
  3. Divide the solution between three test tubes. To the first add seven drops of ethanoic anhydride.
  4. To the second add 1 cm3 of glacial ethanoic acid and 1 cm3 of sodium nitrite solution.
  5. To the third add a small spatula measure of sodium carbonate.
58
Q

What is an amide

A

compounds with an amine group directly bonded with a carbonyl group.

59
Q

How to form amides

A

products of reactions with acyl chlorides with either ammonia or amines.

60
Q

Primary / secondary / tertiary amides

61
Q

How to form primary amides using ammonia

62
Q

How to form secondary amides from primary amines

63
Q

What is optical isomerism

A

• non-superimposable mirror image structures

64
Q

What do optical isomers have

A

chiral center – normally a carbon atom that is attached to 4 different atoms or groups of atoms

65
Q

Draw general structure of a pair of optical isomers

66
Q

How to spot optical isomers

A

4 different molecules bonded off of C – no double bonds

67
Q

Draw optical isomer of this

68
Q

Properties of Optical Isomers

A

• rotate plane-polarised light in different directions i.e. one enantiomer rotates it clockwise

69
Q

What’s a racemic mixture

A

contains equal proportions of each enantiomer will have no effect on plane-polarised light.
o As the rotations cancel out.

70
Q

What is condensation polymerisation

A

• the joining of monomers with the loss of a small molecule = usually water or HCl

71
Q

What does condensation polymerisation need

A

• Two different functional groups

72
Q

Define monomer

A

small molecule combines with many other monomers to form a polymer

73
Q

Define polymer

A

a large molecule formed from many thousands of repeat units of smaller molecules (monomers)

74
Q

Define repeat unit

A

the simplest unit of the polymer that is repeated many times to form the full polymer.

75
Q

How can polyesters be made

A
  • from one monomer containing both a carboxylic acid and an alcohol group
  • from two monomers – one containing two carboxylic acid groups (dicarboxylic acid), and one containing two alcohol groups (diol)
  • from diacyl chlorides with diols
76
Q

Polyesters from one monomer - both a carboxylic acid and an alcohol group

77
Q

Polyesters from one monomer - both a carboxylic acid and an alcohol group - how many waters

78
Q

Polyesters from

A

two monomers – one containing two carboxylic acid groups (dicarboxylic acid), and one containing two alcohol groups (diol)

79
Q

Polyesters from two monomers – one containing two carboxylic acid groups (dicarboxylic acid), and one containing two alcohol groups (diol)

80
Q

Polyesters from two monomers – one containing two carboxylic acid groups (dicarboxylic acid), and one containing two alcohol groups (diol) - how many waters

81
Q

Polyesters from diacyl chlorides

82
Q

How to make Polyamides

A
  • from one monomer containing both an amine and a carboxylic acid group/acyl chloride
  • from two monomers – one containing two carboxylic acid groups (dicarboxylic acid) or two acyl chlorides, and one containing two amine groups (diamine)
83
Q

Polyamides - • made from one monomer containing both an amine and a carboxylic acid group/acyl chloride

84
Q

Polyamides - • made from one monomer containing both an amine and a carboxylic acid group/acyl chloride - water

85
Q

Polyamide - from two monomers – one containing two carboxylic acid groups (dicarboxylic acid) or two acyl chlorides, and one containing two amine groups (diamine)

86
Q

Polyamide - from two monomers – one containing two carboxylic acid groups (dicarboxylic acid) or two acyl chlorides, and one containing two amine groups (diamine) - how many waters

87
Q

Hydrolysis of Polyamides + polyesters

A

using hot aq. acid (eg. HCl) OR hot aq. alkali (eg. NaOH)

88
Q

Hydrolysis of polyesters in acid and base

89
Q

Hydrolysis of polyamides in acid and base

90
Q

examples of carbon-carbon bond formation

A

acylation / alkylation of benzene

91
Q

how to form nitrile

A

2 ways

from aldehyde / ketone

from haloalkane

92
Q

how to form a nitrile from aldehyde / ketone

A

reacted with NaCN and H2SO4

(which generates HCN in situ).​

93
Q

ketone/ aldehyde to nitrile name

A

nucleophilic addition

94
Q

mechanism for ketone to nitrile

A

nucleophilic addition

95
Q

how to form a nitrile from a haloalkane

A

reacted with NaCN/KCN in ethanol​

96
Q

haloalkane to nitrile name

A

nucleophilic substitution

97
Q

mechanism from haloalkane to nitrile

A

nucleophilic substitution

98
Q

reactions of nitriles

A

reduced to amines

hydrolysed to COOH

99
Q

how to turn nitriles into amines

A

reduction

H2 + Ni catalyst

100
Q

how to turn nitriles into COOH

A

heat and aq acid dilute (HCl)

101
Q

what are Grignard reagents.​

A

Organometallic compounds that provide a source of nucleophiles called carbanions

(C has a negative charge)​

102
Q

reactions of Grignard reagents

A

with aldehydes / ketones to form alcohols WITH LONGER CARBON CHAIN

103
Q

conditions for aldehyde / ketone to alcohol via Grignard reagents

A

Aldehydes and ketones can be reacted with Grignard reagents

followed by dilute aq. acid

104
Q

type of reaction aldehyde / ketone to alcohol

A

nucleophilic addition

105
Q

mechanism for aldehyde / ketone to alcohol via Grignard reagents

Chemistry - Module 6 (5 decks)

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