Chapter 28, 29 and 30 - Amines, Polymerisation, DNA Flashcards

1
Q

What are amines

A

They are compounds derived from ammonia
They have unpleasant ‘fishy’ odours

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2
Q

How are amines named

A

Suffix -amine
Prefix amino-

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3
Q

What are the 4 types of amines

A

Ammonia
Primary amine
secondary amine
tertiary amine
Quaternary salts - not amines

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4
Q

What is the structure of an aliphatic amine

A

It has an alkyl group attached to the N

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5
Q

What is the structure of an aromatic amine

A

It has the nitrogen attached directly to a benzene ring

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6
Q

What is a quaternary salt

A

It is a nitrogen with a positive charge attached to 4 molecules

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7
Q

What do amines act as

A

weak Bronsted-Lowry bases

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8
Q

What are Bronsted-Lowry bases

A

Proton acceptors

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9
Q

Why can amines act how they do

A

They have a lone pair on the nitrogen that can readily accept protons

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10
Q

What does the ability of an amine to act as a base depend on

A

How well the lone pair on the nitrogen can accept H+

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11
Q

What is the order of base strength from strongest to weakest

A

Tertiary
Secondary
Primary
NH3
aromatic amine

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12
Q

In aliphatic amines, what causes the ability of a nitrogen to accept H+ to increase

A

alkyl groups push electrons towards the nitrogen increasing the availability of the N lone pair
Increasing the ability to accept H+
inductive effect

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13
Q

In aromatic amines, what causes the ability of a nitrogen to accept H+ to decrease

A

The N lone pair is partially delocalised into the benzene ring, reducing the availability of the N lone pair so reducing its ability to accept H+
Reducing the base strength

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14
Q

What are aromatic amines used as

A

Used in the manufacture of dyes

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15
Q

How are aromatic amines made

A

Reduction of aromatic nitro compounds
Sn + HCl

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16
Q

How are primary aliphatic amines made

A

2 stages
From Haloalkane

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17
Q

What is the first stage of making primary aliphatic amines

A

Nucleophilic substitution
Add CN- in Aqueous Alcohol
Form nitrile
CH3Br + CN- -> CH3CN + KBr

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18
Q

What is the second stage of making primary aliphatic amines

A

Reduction
Ni catalyst
From nitrile to primary amine
CH3CN + 2H2 -> CH3CH2NH2

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19
Q

What is the other method to making primary aliphatic amines

A

Haloalkanes react with excess of concentrated ammonia
nucleophilic substitution
CH3Br + 2NH3 -> CH3NH2 + NH4Br

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20
Q

What is the mechanism for making a primary aliphatic amine the other method

A

Nucleophilic substitution
Lone pair on NH3 attacks carbon
Breaks bond between carbon and bromine towards bromine
Lone pair on NH3 attacks hydrogen
Bond between hydrogen and nitrogen breaks towards nitrogen

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21
Q

What are the advantages and disadvantages of making a primary aliphatic amine the second method

A

1 step
Doesn’t add another carbon to product
Reaction can repeat and form multiple products

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22
Q

What can happen in the second method after the intial reaction

A

The product can act as a nucleophile to another haloalkane
This causes further reactions forming a mixture of primary, secondary, tertiary amines and quaternary salts
This method can’t be used to make amines

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23
Q

In the second method what is the main product with excess NH3

A

primary amine

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24
Q

In the second method what is the main product with excess haloalkane

A

quaternary salt

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25
Q

What do amino acids contain

A

Amine group
Carboxylic acid

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26
Q

What are alpha amino acids

A

Amino acid with 1 carbon between the NH2 and COOH group

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27
Q

What do amino acids exist as in the solid state

A

zwitterions

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28
Q

Why do amino acids exist as zwitterions

A

Ionic
High melting point
Usually solids at room temperature
Soluble in water

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29
Q

What do zwitterions look like

A

Carboxylic acid is COO-
Amine is NH3+

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30
Q

When dissolved in water, what are amino acids sensitive to

A

pH

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31
Q

What do amino acids look like at a low pH

A

Amine is protonated - NH3+
Acid is undissociated - COOH

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32
Q

What do amino acids look like at a high pH

A

Amine unprotonated - NH2
Acid dissociated - COO-

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33
Q

What are the reactions of amino acids like

A

It involves either the amine or carboxylic acid group

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34
Q

What reactions does the amine group do

A

Protonated by acids (low pH)
Acylation with acyl chloride/acid anhydride
Nucleophilic substitution with haloalkanes

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35
Q

What reactions does the carboxylic acid in the amino acid do

A

Deprotonated by bases (high pH)
Acylation with esterification with alcohols (conc H2SO4 catalyst)

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36
Q

What product is made from reacting 2 amino acids

A

peptides + water

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37
Q

What is the peptide link

A

The bond between the 2 amino acids
CO -NH
COOH loses OH
NH2 loses H

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38
Q

What are addition polymers

A

They are long chain molecules formed from lots of small molecules (monomers) joined together to form 1 big molecule (polymer)

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39
Q

How are addition polymers formed

A

When alkenes undergo self addition

40
Q

What is the monomer structure

A

The structure of the monomer by itself

41
Q

What is the polymer structure

A

The monomer structure when in the polymer with brackets around outside bonds

42
Q

What is the repeating unit

A

The monomer structure with bonds to other monomers

43
Q

What are condensation polymers

A

Long chain molecules formed from lots of small molecules (monomers) join together to form 1 big molecule (polymer) with another small molecule formed as well

44
Q

What are condensation polymers normally made from

A

2 different monomers each with 2 functional groups that can react together

45
Q

What are polyesters formed from

A

Dicarboxylic acids with diols

46
Q

What is the bond between polyesters

A

OH from COOH
H from OH react together to form water
Forms COO bond

47
Q

What is an example of polyesters

A

Terylene
Made from benzene-1,4-dicarboxylic acid and ethane-1,2-diol

48
Q

What are polyamides

A

Polymers formed from dicarboxylic acid and diamines
Form peptide link

49
Q

What is an example of polyamides

A

nylon - 6,6
Kevlar

50
Q

What are addition polymers known as

A

Plastics

51
Q

What are polyalkenes

A

addition polymers
saturated

52
Q

What are the properties of addition polymers

A

unreactive
chemically inert

53
Q

What are the advantages of the properties of addition polymers

A

Safe
Durable

54
Q

What are the disadvantages of the properties of addition polymers

A

Don’t biodegrade
Pollution hazard
Difficult to dispose of

55
Q

How are Non-Biodegrable polymers disposed of

A

Landfill
Incineration
Recycling

56
Q

What is Landfill

A

Polymers are buried in sites dedicated to waste
Land available is limited though

57
Q

What is incineration

A

Polymers are burned
Releases lots of heat energy which can be used to generate electricity
Carbon Dioxide is released - global warming
Toxic gases can also be produced under certain conditions

58
Q

What is recycling

A

Reusing polymers
Not always practical - expensive to separate
Protects the useful hydrocarbon resources

59
Q

What does the amide and ester links in poly amides and polyesters do

A

They can react with acids and bases causing the polymer structure to break reforming the monomers
Called hydrolysis

60
Q

What are the properties of condensation polymers

A

Biodegradable

61
Q

What are molecules formed up to 50 amino acids joined together known as

A

Polypeptides

62
Q

What are molecules with more than 50 amino acids joined together known as

A

Proteins

63
Q

What are proteins

A

Polymers of amino acid monomers

64
Q

What are the 3 structures of proteins

A

Primary
Secondary
Tertiary

65
Q

What is the primary protein structure

A

Amino acids joined in a chain

66
Q

What is the secondary protein structure

A

Amino acids form a beta-pleated sheet or a alpha helix
Folding of its polypeptide chain

67
Q

What are the tertiary protein structures

A

A combination of the beta-pleaded sheets and alpha-helix’s

68
Q

What causes secondary protein structures

A

Hydrogen bonding interactions between C=O and N-H groups from different sections of the chain

69
Q

How do the hydrogen bonds form

A

Nitrogen and oxygen are electronegative so C=O and N-H bonds are polar
Lone pair on oxygen atom is attracted to delta positive hydrogen of N-H forming a hydrogen bond

70
Q

What bonds are there in a tertiary structure

A

Van Der Waals forces
Hydrogen bonds
Ionic Bonds
Disulphide bridges (covalent bonds)

71
Q

How can peptides be broken down

A

By hydrolysis
Produces individual amino acids that they were formed from

72
Q

What are conditions for hydrolysis

A

HCl and boil for 24 hours
or
Enzyme

73
Q

What are enzymes

A

They are protein molecules that act as biological catalysts
They have an active site where the reaction takes place

74
Q

What do enzymes react with

A

Molecules called substrates

75
Q

Why do enzymes only work with certain substrates

A

The active sites are very particular shapes
They are stereospecific

76
Q

What are inhibitors

A

Molecules with similar shape to the active site can compete with the substrate molecules
They can block the active site so no substrate fits in

77
Q

How do many drugs work

A

Using enzyme inhibition
e.g. aspirin, penicillin

78
Q

What is DNA stand for

A

deoxyribonucleic acid

79
Q

What is DNA

A

A polymer
Present in all living cells
Formed from nucleotides (monomers) join together

80
Q

What is the structure of DNA

A

There are 2 polynucleotide chains (strands) spiralled together in a double helix structure

81
Q

What is a nucleotide

A

Phosphate bonded to a deoxyribose sugar which is bonded to a base

82
Q

What are the bases

A

Adenine
Guanine
Cytosine
Thymine

83
Q

How is a nucleotide formed

A

Phosphate attaches to the 5th carbon in the sugar
N-H on Base attaches to the 1st carbon

84
Q

How does the phosphate bond to the sugar

A

H from OH on phosphate and OH from sugar react
Bond between Oxygen and CH2

85
Q

How does the phosphate from the other nucleotide bond onto the sugar

A

OH on phosphate reacts with H on the 3rd carbon on the sugar
Produces water

86
Q

How are the 2 strands of DNA held together

A

Base pairing

87
Q

How are the bases paired

A

Adenine - Thymine
Cytosine - Guanine

88
Q

How do the bases bond together

A

AT - Bond between NH and O
Bond between N and NH
GC - Bond between O and NH
Bond between NH and N
Bond between NH and O

89
Q

What are the 2 strands described as

A

complementary

90
Q

What is cisplatin

A

A complex of platinum(ll) with 2 chlorides and 2 ammonia ligands
Successful anti-cancer drug

91
Q

What causes cancer

A

When cells in the body divide and replicate uncontrollably forming tumours

92
Q

How do cells divide

A

A cell replicates its DNA
The strands unwind so they can be copied

93
Q

How does cisplantin work

A

It attaches to N atoms of nearby guanine bases in DNA
Ligand replacement reaction
This stops strands unwinding so the cell can’t replicate properly

94
Q

What are the side effects of cisplantin

A

Hair loss
Nausea
Immunosuppresion

95
Q

What are the solutions to the side effects of cisplantin

A

Use lowest therapeutic dose
Develop new drugs
Find ways of targeting the cancer cells directly

96
Q

Why don’t addition polymers undergo hydrolysis

A

The c-c bonds are too strong
Or No polar groups/Non-polar
Depends on alkene

97
Q

What are the uses of quaternary salts

A

Hair conditioner / disinfectant