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Module 6- Organic Chemistry > 27 Amines, amino acids, and polymers > Flashcards

27 Amines, amino acids, and polymers Flashcards

1
Q

What is optical isomerism? (1 mark)

A

When the mirror images of molecules are non-superimposable.

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2
Q

What is a chiral carbon atom? (1 mark)

A

A carbon atom that has four different groups attached to it.

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3
Q

What are two compounds that are optical isomers of each other called? (1 mark)

A

Enantiomers

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4
Q

What is a 50/50 mixture of two enantiomers called? (1 mark)

A

A racemic mixture/ racemate

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5
Q

What is the main difference between optical isomers? (1 mark)

A

They affect plane polarised light differently.

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6
Q

Why does a racemate have no effect on the plane of light? (1 mark)

A

Each enantiomer rotates the plane polarised light by the same amount, but in the opposite direction.
This means the effects of the enantiomers cancel out.

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7
Q

What is the functional group of an amine? (1 mark)

A

NH2

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8
Q

What are amines derived from? (1 mark)

A

Ammonia

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9
Q

What are the two types of amines? (2 marks)

A

Aliphatic amine
Aromatic amine

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10
Q

What is an aliphatic amine? (1 mark)

A

The nitrogen atom is attached to at least one carbon chain.

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11
Q

What is an aromatic amine? (1 mark)

A

The nitrogen atom is attached to an aromatic ring.

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12
Q

What is a primary amine? (1 mark)

A

The nitrogen is attached to one a carbon chain.

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13
Q

What is a secondary amine? (2 marks)

A

The nitrogen is attached to 2 carbon chains.

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14
Q

What is the tertiary amine? (3 marks)

A

The nitrogen is attached to 3 carbon chains.

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15
Q

How do you name secondary/tertiary amines? (2 marks)

A

Call it an N-substituted derivative of the larger group.

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16
Q

What is serotonin? (2 marks)

A

An amine that acts as a neurotransmitter, controlling sleep, appetite, memory and many other things.

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17
Q

What is pseudoephedrin? (2 marks)

A

An amine that is used in decongestion medications.

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18
Q

Why do amines act as bases in chemical reactions? (1 mark)

A

They have a lone pair of electrons on the N that can accept a proton.

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19
Q

What is the name of an amine ion? (1 mark)

A

ammonium ion

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20
Q

How do amines react with acids? (1 mark)

A

Amines neutralise amines to make salts.

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21
Q

How do you prepare a primary aliphatic amine, using a haloalkane? (3 marks)

A

Ammonia + haloalkane–> Ammonium salt
Ammonium salt + alkali (aq) –> amine

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22
Q

What are the conditions required to prepare an aliphatic amine from a haloalkane, and explain why they are used? (4 marks)

A

ethanol- prevents substitution of haloalkane by water to produce alcohols
excess ammonia- reduces further substitution

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23
Q

How do you prepare a secondary/tertiary amine, using a haloalkane? (2 marks)

A

Prepare a primary amine
Primary amine + haloalkane –> ammonium salt
ammonium salt + alkali (aq) –> amine

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24
Q

How do you prepare an aromatic amine? (3 marks)

A

Reduction of nitrobenzene- heated under reflux with tin and HCl
Add excess NaOH

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25
What functional groups do amino acids contain? (2 marks)
NH2 COOH
26
How do amino acids react with acids? (2 marks)
The amine group is basic, and react with acids to make salts.
27
How do amino acids react with aqueous alkalis? (2 marks)
The carboxylic acid group reacts with the alkali to form a salt.
28
How do amino acids react with alcohols? (2 marks)
The carboxylic acid group reacts with the alcohol to form an ester.
29
What are the conditions required to form an ester from an amino acid? (2 marks)
heating alcohol concentrated sulfuric acid
30
What are amides the products of? (2 marks)
acyl chloride + ammonia/amines
31
What is the functional group of an amide? (2 marks)
Carbonyl group bonded to a nitrogen. CON or CONH or CONH2
32
What is a primary amide? (1 mark)
The nitrogen is attached to one a carbon chain.
33
What is a secondary amide? (1 mark)
The nitrogen is attached to two carbon chains.
34
What is a tertiary amide? (1 mark)
The nitrogen is attached to three carbon chains.
35
Do amines have hydrogen bonds between molecules, why/why not? (2 marks)
Yes, they contain N-H bonds.
36
Explain why a tertiary amine has a much lower boiling point than primary and secondary amines of similar Mr. (2 marks)
They have no hydrogen atoms directly attached to the nitrogen, so hydrogen bonding cannot happen between molecules.
37
What is trend in solubility of amines as their caron chains get longer, why? (2 marks)
Less soluble as carbon chains increase in length, because they force their way between water molecules, breaking the hydrogen bonds between water molecules and nitrogens in amines.
38
Draw the mechanism of the production of an amine from a haloalkane. (6 marks)
Step 1: 1. Curly arrow from ammonia to carbon bonded to halogen in haloalkane 2. Curly arrow from bond C-halogen bond to halogen Step 2: 3. Ammonia is now bonded to carbon chain from haloalkane in intermediate 4. Curly arrow from N-H bond to N+ 5. Curly arrow from released another ammonia molecule to hydrogen 6. Correct product
39
Describe how an amine is produced by the reduction of a nitrile compound, in a lab, include the reagents and conditions. (4 marks)
1. haloalkane + KCN --> nitrile compound 2. nitrile compound + 4[H] --> amine LiAlH4 in ethoxyethane
40
Describe how an amine is produced by the reduction of a nitrile compound, in industry, include the reagents and conditions. (4 marks)
1. haloalkane + KCN --> nitrile compound 2. nitrile compound + 2H2 --> amine Ni catalyst + heat
41
Why is phenylamine a weaker base than ammonia? (2 marks)
The lone pair of electrons on the nitrogen of the phenylamine is delocalised into the benzene ring, making it less available to combine with hydrogen ions.
42
What zwitterton does an amino acid exist as at a low pH? (1 mark)
The NH2 group is protonated to NH3+
43
What zwitterton does an amino acid exist as at a neutral pH? (2 marks)
The NH2 group is protonated to NH3+ The COOH group is unprotonated to COO-
44
What zwitterton does an amino acid exist as at a high pH? (1 mark)
The COOH group is unprotonated to COO-
45
What is condensation polymerisation? (1 mark)
The joining of monomers with the loss of a small molecule (usually H20/HCl)
46
What links the monomers in polyesters? (1 mark)
Ester linkages
47
What functional groups must a monomer contain to turn a polyester by condensation polymerisation? (2 marks)
COOH and OH
48
A polyester is made of two monomers, what functional groups must each monomer contain? (2 marks)
One contains 2 COOH groups One contains 2 OH groups
49
What is lactic acid derived from? (1 mark)
Maize
50
Give an example of a polyester formed from one monomer. (1 mark)
Poly (lactic acid) Poly (glycolic acid)
51
Give an example of a polyester formed from two monomers. (1 mark)
Treylene (PET)
52
What links the monomers in polyamides? (1 mark)
Amide linkages
53
What functional groups must a monomer contain to turn a polyamide by condensation polymerisation? (2 marks)
COOH/COCl and NH2
54
A polyamide is made of two monomers, what functional groups must each monomer contain? (2 marks)
One contains 2 COOH/COCl groups One contains 2 NH2 groups
55
What type of polymer do amino acids form, why? (2 marks)
Polyamide Contain a COOH and a NH2
56
How are condensation polymers hydrolysed? (1 mark)
Using an **aqueous, hot** acid/alkali
57
What is formed when a polyester undergoes acid hydrolysis? (2 marks)
Alcohol Carboxylic acid
58
What is formed when a polyester undergoes alkali hydrolysis? (2 marks)
Alcohol A carboxylic salt
59
What is formed when a polyamide undergoes acid hydrolysis? (2 marks)
Carboxylic acid Ammonium ion
60
What is formed when a polyamide undergoes alkali hydrolysis? (2 marks)
Amine A carboxylic salt
61
Why are condensation polymers biodegradable? (2 marks)
Because contain C-O or C-N polar bonds in the main chain, which are susceptible to chemical attack.
62
What are the strongest forces between polymer chains in addition polymers? (1 mark)
Induced dipole-dipole interactions
63
What are the strongest forces between polymer chains in polyesters? (1 mark)
Permanent dipole-dipole interactions
64
What are the strongest forces between polymer chains in polyamides? (1 mark)
Hydrogen bonds

Module 6- Organic Chemistry (5 decks)

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