27- Amines, Amino Acids And Polymers Flashcards
(105 cards)
1
Q
Primary amine
A
1 R group
2
Q
Secondary amine
A
2 R groups
3
Q
Tertiary amine
A
3 R groups
4
Q
Ammonia
A
0 R groups
5
Q
Characteristics of amines
A
• Pungent smell
• Physiological effects
o Amphetamine (Treats fatigue)
o Phenylephrine (Decongestant)
o Adrenaline (Stress hormone)
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
7
Q
Name this
A
Ethylamine
8
Q
Name this
A
2-aminobutane
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.
10
Q
Name these
A
11
Q
Name these
A
12
Q
What do amines behave as
A
Weak bases
13
Q
Why do they behave as weak bases
A
o Lone pair on N atom can accept a proton
14
Q
What are amines
A
Bases
15
Q
How to form a salt from an amine
A
• Acid + Amine -> Ammonium Salt
16
Q
Write reaction between HCl and propylamine
A
17
Q
Write reaction between Sulfuric acid and butylamine
A
18
Q
What type of reaction are these
A
Neutralisation
19
Q
Name or mechanism that prepares primary aliphatic amines
A
Nucleophilic substitution
20
Q
Type of reaction that prepares primary aliphatic amines
A
2 step
21
Q
How to prepare primary aliphatic amines - overall
A
- Salt formation
- Amine formation
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
23
Q
Step 2 of primary amine preparation - amine formation
A
• Ammonium salt reacts with sodium hydroxide
24
Q
Conditions of primary amine formation
A
- ethanol solvent
- excess ammonia
25
Why ethanol solvent condition - primary amine formation
Prevents substitution of haloalkane with water (to form alcohols)
26
Why excess ammonia condition - primary amine formation
Reduces further substitution of the amine to form secondary and tertiary amines
27
Preparation of secondary aliphatic amines - 2 step
28
Preparation of tertiary aliphatic amines - 2 step
29
Why can we prepare secondary / tertiary amines this way
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
30
Nucleophile in preparation of amines
Ammonia / amine
31
Preparation of aromatic amines - 2 steps overall
Salt formation
Amine formation
32
Preparation of aromatic amines - salt formation - conditions
- Tin and conc. HCl act as a reducing agent
- Heated under reflux
33
Preparation of aromatic amines - amine formation - conditions
- Excess NaOH (aq) is added to produce the aromatic amine
34
Type of reaction for Preparation of aromatic amines
• Nitroarenes are reduced to form aromatic amines.
35
Wrote equation for formation of phenylamine
36
How many natural amino acids in body
20
37
Type of natural body amino acids
Alpha
38
What is an alpha amino acid
o amine is attached to the alpha C - one carbon separating two functional groups
39
Naming alpha amino acids
• carboxylic acid group takes priority = amine group will always be at position 2 in an α-amino acids (2-amino).
40
Name
41
Reactions of Amino acids - list
• with acids
• with alkalis
• with alcohols
42
Reaction of amino acid with acids
• basic -NH₂ can react with acids to form ammonium salt
43
Reaction between amino acids and acids
• basic -NH₂ can react with acids to form ammonium salt
44
Draw reaction between alanine and HCl
45
Reactions of amino acids with alkalis
• -COOH can react with alkalis (such as NaOH or KOH) to form salt + water.
46
Draw general reaction between amino acid + NaOH
47
Reaction between amino acids and alcohol + CONDITIONS
• -COOH can easily be esterified by heating with an alcohol in the presence of conc. H₂SO4 catalyst.
48
Reaction between amino acids + alcohols are in acidic conditions - remember reaction conditions - why is this significant
basic amine group is protonated.
49
Write draw reaction between alanine and ethanol
50
How do Zwitterions form
the basic -NH₂ can accept a proton from the –COOH to form an ion containing both a +ve and –ve charge.
51
What’s the isoelectric point
• pH at which the zwitterion is formed
52
What’s special about the isoelectric point
• Each amino acid has its own unique isoelectric point.
53
If pH is higher then isoelectric
amino acid acts as an acid, and loses a proton from -COOH
54
If pH is lower than isoelectric
amino acid acts as a base, and accepts a proton in -NH2
55
Spectrum of pH
56
Properties of amino acids
• Bifunctional – act as acid and base
57
Investigate properties of amino acids- method
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
What is an amide
compounds with an amine group directly bonded with a carbonyl group.
59
How to form amides
products of reactions with acyl chlorides with either ammonia or amines.
60
Primary / secondary / tertiary amides
61
How to form primary amides using ammonia
62
How to form secondary amides from primary amines
63
What is optical isomerism
• non-superimposable mirror image structures
64
What do optical isomers have
chiral center – normally a carbon atom that is attached to 4 different atoms or groups of atoms
65
Draw general structure of a pair of optical isomers
66
How to spot optical isomers
4 different molecules bonded off of C – no double bonds
67
Draw optical isomer of this
68
Properties of Optical Isomers
• rotate plane-polarised light in different directions i.e. one enantiomer rotates it clockwise
69
What’s a racemic mixture
contains equal proportions of each enantiomer will have no effect on plane-polarised light.
o As the rotations cancel out.
70
What is condensation polymerisation
• the joining of monomers with the loss of a small molecule = usually water or HCl
71
What does condensation polymerisation need
• Two different functional groups
72
Define monomer
small molecule combines with many other monomers to form a polymer
73
Define polymer
a large molecule formed from many thousands of repeat units of smaller molecules (monomers)
74
Define repeat unit
the simplest unit of the polymer that is repeated many times to form the full polymer.
75
How can polyesters be made
- 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
Polyesters from one monomer - both a carboxylic acid and an alcohol group
77
Polyesters from one monomer - both a carboxylic acid and an alcohol group - how many waters
N-1
78
Polyesters from
two monomers – one containing two carboxylic acid groups (dicarboxylic acid), and one containing two alcohol groups (diol)
79
Polyesters from two monomers – one containing two carboxylic acid groups (dicarboxylic acid), and one containing two alcohol groups (diol)
80
Polyesters from two monomers – one containing two carboxylic acid groups (dicarboxylic acid), and one containing two alcohol groups (diol) - how many waters
2n-1
81
Polyesters from diacyl chlorides
82
How to make Polyamides
- 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
Polyamides - • made from one monomer containing both an amine and a carboxylic acid group/acyl chloride
84
Polyamides - • made from one monomer containing both an amine and a carboxylic acid group/acyl chloride - water
N-1
85
Polyamide - from two monomers – one containing two carboxylic acid groups (dicarboxylic acid) or two acyl chlorides, and one containing two amine groups (diamine)
86
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
2n-1
87
Hydrolysis of Polyamides + polyesters
using hot aq. acid (eg. HCl) OR hot aq. alkali (eg. NaOH)
88
Hydrolysis of polyesters in acid and base
89
Hydrolysis of polyamides in acid and base
90
examples of carbon-carbon bond formation
acylation / alkylation of benzene
91
how to form nitrile
2 ways
from aldehyde / ketone
from haloalkane
92
how to form a nitrile from aldehyde / ketone
reacted with NaCN and H2SO4
(which generates HCN in situ).
93
ketone/ aldehyde to nitrile name
nucleophilic addition
94
mechanism for ketone to nitrile
nucleophilic addition
95
how to form a nitrile from a haloalkane
reacted with NaCN/KCN in ethanol
96
haloalkane to nitrile name
nucleophilic substitution
97
mechanism from haloalkane to nitrile
nucleophilic substitution
98
reactions of nitriles
reduced to amines
hydrolysed to COOH
99
how to turn nitriles into amines
reduction
H2 + Ni catalyst
100
how to turn nitriles into COOH
heat and aq acid dilute (HCl)
101
what are Grignard reagents.
Organometallic compounds that provide a source of nucleophiles called carbanions
(C has a negative charge)
102
reactions of Grignard reagents
with aldehydes / ketones to form alcohols WITH LONGER CARBON CHAIN
103
conditions for aldehyde / ketone to alcohol via Grignard reagents
Aldehydes and ketones can be reacted with Grignard reagents
followed by dilute aq. acid
104
type of reaction aldehyde / ketone to alcohol
nucleophilic addition
105
mechanism for aldehyde / ketone to alcohol via Grignard reagents
