Amines Flashcards
(92 cards)
1
Q
It is an organic compound that contain nitrigen atims with a lone pair.
A
Amines
2
Q
It is derived from ammonia (NH3) in which one or more hydrogen atoms is replaced by an alkyl or aryl group.
A
Amines
3
Q
Amines is biologically significant to:
A
- Amino acid
- DNA
- RNA
- base
- Alkaloids
4
Q
General Formula:
R-NH2
A
Primary Amine
5
Q
General Formula:
R2-NH
A
Secondary Amine
6
Q
General Formula:
R3-N
A
Tertiary Amine
7
Q
General Formula:
R4-N(+) X(-)
A
Quarternary
8
Q
General Formula:
R3-N
A
Tertiary Amin
9
Q
As per VSEPR theory, nitrogen present in amines is sp3 hybridized and due to the presence of a lone pair, it is ____ instead of ______ shape which is a general structure for most sp3 hybridized molecules.
A
it is pyramidal instead of tetrahedral shape
10
Q
Literally means “triangle which have 3 face”
A
Pyramidal
11
Q
“having four faces”
A
Tetrahedral
12
Q
VSEPR theory
A
Valence Shell Electron Pair Repulsion theory
13
Q
When one of the hydrogen atoms of
the ammonia molecule is replaced by an
alkyl or aryl group.
A
Primary Amines
14
Q
Two organic substituents replace the
hydrogen atoms of the ammonia molecule
forming an amine.
A
Secondary Amines
15
Q
When all 3 of the hydrogen atoms are
replaced by an organic substituent, it could
be an aryl or aromatic group.
A
Tertiary Amines
16
Q
These are secondary or tertiary amines in an aromatic ring structure.
A
Cyclic Amines
17
Q
Ring structures that have one or more nitrogen contained within the ring.
A
Heterocyclic Amines
18
Q
Nomenclature of Amines
A
Step 1. Identify the longest carbon chain bonded to the amine nitrogen.
Step 2. Identify the substituents.
Step 3. Number the parent chain giving the amine the lowest locant.
Step 4. Put everything together having the substituents in alphabetical order.
19
Q
Different way if Naming Amines
A
- Naming Primary Amines: Systematic and Common Names
- Naming Compounds with Multiple Functional Group.
- Naming a Compound Where the Amino group is Not the Highest Priority
- Naming Secondary and Tertiary Amines
20
Q
Naming a Primary Amine: Sytematic Names
A
Drope the “e”, change the suffix to “amine”
21
Q
Naming a Primary Amine: Common Names
A
Treat the carbon chain as an alkyl and add to the suffix “amine”
22
Q
Nomenclature of Primary Amines
A
- Locate longest carbon chain that contains the - NH2 group.
- Treat -NH2 group as a branch with the name amino.
- Assign location so that the lowest possible number is used.
- If other branches are present, number and name as with other compounds.
- Alternate system uses ‘amine’ ending instead of amino branch name.
23
Q
Naming Primary Amine:
Always remember to _____ the parent chain giving the
amine the _________
A
- number
- lowest locant
24
Q
Naming Primary Amine:
When other groups are present on the ring, it is numbered _______________ depending on which direction gives the next substituent the lower number
A
clockwise or counterclockwise
25
Naming Primary Amine:
Example
CH3CH2CH2NH2
1-aminopropane
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Naming Primary Amine:
Example
CH3CH(NH2)CH3
2-aminopropane
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Naming compounds with Multiple Functional Group
The parent chain must contain the carbon bonded
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Naming compounds with Multiple Functional Group
The parent chain must contain the carbon bonded
29
Naming compounds with Multiple Functional Group
The parent chain must contain the carbon bonded
30
Naming compounds with Multiple Functional Group
- The parent chain must contain the carbon bonded to the NH2 group
- Number the carbon chain to give the NH2 group the lower number
31
Naming a Compound Where the Amino group is Not the Highest Priority
substituent (lowest priority) Prefix-Parent Chain-Suffix Principal group (highest priority)
32
Naming Secondary and Tertiary Amines
Step 1. Find the parent chain - longest carbon chain bonded to N
Step 2. Name the other groups as alkyls preceeded by an "N"
Step 3. Write the substituents followed by the parent chain with "amine"
33
If the secondary or a tertiary amine has more than one type of alkyl group, then it is named as a ______
primary amine
34
Naming Secondary and Tertiary Amines:
Remember: List the substituents in _______ regardless of whether they are connected to the ______ or the _________
- alphabetical order
- nitrogen
- parent chain
35
Naming Secondary and Tertiary Amines:
Example
CH3CH2CH2 - NH - CH3
N - methyl - 1 - aminopropane
36
Amine Nomencalture:
Some common names (special names that have been accpeted as IUPAC names)
- methyl amine CH3 - NH2
- dimethyl amine CH3 - NH - CH3
- ethyl amine CH3 - CH2 - NH2
- methyl ethyl amine CH3 - NH - CH2 - CH3
37
Uses of Amines
- uses in pharmaceutical industry
- pest control and tanning of leather
- use in making azo-dyes and nylon
- personal care
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Uses of Amines:
In pharmaceutical industry, _____ and _____ are used as ______ that are pain killers
- morphine and demerol
- analgesics
39
Uses of Amines:
It is used as anaesthetic
Novocaine
40
Uses of Amines:
A very common decongestant
Ephedra
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Uses of Amines:
It is used for disinfecting drinking water
Tetramethyl Ammonium Iodine
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Uses of Amines:
Are recreational drugs
Methamphetamines and amphetamines
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Uses of Amines:
A primary nuerotransmitter that controls the feeling of hunger and the speed with which the brain functions generally.
Serotonin
44
Uses of Amines:
Are the most common type of amine used in the global market.
Ethanol Amines
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Sources of Amines
Industrial sources
Production from ammonia and alcohol
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Basicity of Amines results in ____
salt formation
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Example of Heterocyclic drugs
Cocaine
lysergic acid diethylamide (LSD)
Viagra
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Properties of Amines:
have higher boiling points since they can form hydrogen bonds with each other as well as van der Waals dispersion forces and dipole-dipole interaction.
Primary Amines
49
Properties of Amines:
has a little lower boiling point than the corresponding primary amine with the same number of carbon atoms. Secondary amines still form hydrogen bonds, but having the nitrogen atom in the middle of the chain rather than at the end makes the permanent dipole on the molecule slightly less
Secondary Amine
50
Properties of Amines:
there aren't any hydrogen atoms attached directly to the nitrogen. That's why the boiling point is much lower.
Tertiary Amines
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Physical Properties of Amines:
______ and ______ have hydrogen atoms bonded to an nitrogen atom and are therefore capable of hydrogen bonding
Primary and Secondary Amines
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Solubility:
are more soluble due to their ability to donate and accept hydrogen bonds.
Primary and Secondary amines
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Solubility:
are less soluble as they can only accept hydrogen bonds from water molecules
Tertiary Amines
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Solubility:
When there is an _____ in the hydrophobic alkyl part of the amines, its molar mass _____. As a result, such amines have a __________ in water
- increase
- goes up
- lower solubility
55
Solubility:
Amines are soluble in organic solvents like _____, _____, and
______ because alcohols have _______ as compared to amines.
- alcohol
- ether
- benzene
- high polarity
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Density
ranging from 0.6 to 1.0 g/cm³
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Application of Amines:
In chemical industry
they serve as surfactants, corrosion inhibitors, and solvents
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Application of Amines:
_____, ____, and _____ are all made from amines
as well
Pharmaceuticals, dyes, and pigments
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Application of Amines:
In creation of polyuethane foams as well as curing agents in epoxy resins.
they serve as blowing agents
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Application of Amines:
Amines are also utilized to make _____ and ______
insecticides and herbicides
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Application of Amines:
Amine are significant _______ and ______ in the field of biology
neurotransmitters and hormones
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Types of chemical reaction
- Decomposition
- Synthesis
- Single-replacement
- Double-replacement
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One compound breaks down into two products
Decomposition
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Two or more substances join and form one single substance
Synthesis
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Atoms of an element swap with atoms of a second element in a compound
Single-replacement
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Positive ions exchange between two compounds
Double-replacement
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Decomposition
AB → A+ B
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Synthesis
A + B → AB
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Single-replacement
AB + C → AC + B
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Double-replacement
AB + CD → AD + CB
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The mass of atoms remains the same before and after a chemical reaction
Law of conservation of mass
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They make up a chemical reaction and are represented in a chemical equation.
Reactants and Products
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Reaction:
Amines can function as ____ and _____ because they have an unshared electron pair.
- bases and nucleophiles
74
Reaction:
Amines give up their electrons when they interact with acids to produce _____.
ammonium salt
75
Reaction:
When interacted with amines, acid halides created ____
substituted amides
76
Reaction of Amines as Nucleophiles:
What is present in all amines that attracts positive parts of other molecules or ions.
an active lone pair of electrons on the very electronegative nitrogen atom
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Reaction with nitrous acid:
Primary amines react with nitrous acid to yield
diazonium salt
78
Reaction with nitrous acid:
Secondary aliphatic and aromatic amines form _____ with nitrous acid
nitrosoamine
79
Reaction with nitrous acid:
Tertiary amines react with nitrous acid to form ______
N‐nitrosoammonium compounds
80
- It is formed by a reaction between nitrates or nitrites and certain amines, with a nitrosating agent
- are formed during some forms of cooking
Nitrosoamines
81
Nitrosoamine as Carcinogen can cause cancer of:
- lungs
- liver
- kidney
- brain
- bladder
- nasal sinus
82
Where are Nitrosamines found?
- meat products
- water
- processed fish
- cocoa
- beer
- tobacco
- alcoholic beverages
83
- also known as diazonium compounds
- are organic compounds that contain the diazonium functional group (-N₂⁺X⁻), where X⁻ represents an anion.
Diazonium Salts
84
Diazonium Salts: Replacement Reaction (or Decomposition)
Diazonium salts can undergo replacement reactions, where the diazonium group is substituted with a different functional group, such as ____, _____, or _____
halides, hydroxyl groups, or cyanide groups
85
Diazonium Salts:
It is a chemical reaction that involves the conversion of primary aromatic amines (diazonium salts) into various functionalized aromatic compounds using copper salts as catalysts.
Sandmeyer Reaction
86
Diazonium Salts:
The reaction was developed by Traugott Sandmeyer in 1884 and is widely used in organic synthesis
Sandmeyer Reaction
87
Diazonium Salts: Sandmeyer Reaction
The Sandmeyer reaction involves the substitution of the diazonium group (N₂⁺X⁻) with a ______ on the ____ ____.
- with a new substituent on the aromatic ring
88
Diazonium Salts: Sandmeyer Reaction
it rects as a catalyst and helps facilitate the reaction.
copper(I) salt
89
Sandmeyer reaction is another use for ____
Cyanation
90
Cyanation allows for the formation of _____, an important class of organic compounds.
benzonitriles
91
Diazonium Salts:
Diazonium salt undergo in this kind of reaction to form a new carbon-carbon or carbon-nitrogen bonds.
Coupling reaction (or diazonium coupling)
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Diazonium Salt: Coupling Reaction
Diazonium salts can undergo coupling reactions with various nucleophiles, such as _____ _____, ______, and ______
aromatic compounds, phenols, and amines
