Chapter 27 - Amines, amino acids Flashcards

1
Q

Define amines

A

They are derived from NH3 (ammonia) in which one or more of the hydrogen atoms in ammonia are replaced by a carbon chain or ring.

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2
Q

Define an aliphatic amine

A

Nitrogen is attached to at least 1 straight chain or branched alkyl chain.

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3
Q

Define aromatic amine

A

Nitrogen is attached to an aromatic ring. (usually nitrobenzene)

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4
Q

What is a primary amine

A

NH2R.

Remember to draw the lone pair of electrons above the N

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5
Q

What is a secondary amine

A

NHR’R’’.
It depends on the number of R groups attached to the N.
Remember to draw the lone pair of electrons on the N.

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6
Q

Examples of amines

A

Serotonin (acts as a neurotransmitter, controlling appetite, sleep, memory, learning and temperature.)
Pseudoephedrine (an active ingredient in decongestion medicines)

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7
Q

How do you name amines

A

Add an ‘amine’ to the end.
Secondary and tertiary amines- add ‘di’ or ‘try’ as a prefix.
When there are 2 or more groups attached to the nitrogen atom, name it as an N- substituted derivative of the larger group.

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8
Q

Smell of amines

A

It smells like rotting fish

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9
Q

Reactions of amines as bases

A

Due to the lone pair on the nitrogen, they can accept a proton, creating a dative covalent bond.
They can react with acids to give salts.
If it is a NH2, it becomes :
NH3+ X-.

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10
Q

Preparation of aliphatic amines

A

The lone pair of electrons on Nitrogen allows ammonia to act as a nucleophile.

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11
Q

How can you create a primary amine

A
  1. Haloalkane + ammonia -> salt.
    Add excess ammonia. (is a nucleophilic substitution)
  2. Salt + NaOH -> primary amine + water + Na-X.
    Ethanol can be used as a solvent to prevent substitution of the haloalkane and production of alcohol.
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12
Q

How can you create a secondary amine

A
  1. Primary amine + haloalkane -> salt.

2. Salt + NaOH -> Na-X + Secondary amine + water.

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13
Q

Preparation of aromatic amines

A

Made by the reduction of nitrobenzene.
Nitrobenzene + 6[H+] -> Phenylamine + 2H20.
above the arrow: 1. Sn/ Concentrated HCl.
2. excess NaOH.

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14
Q

what is an amino acid

A

It contains both amine and carboxylic acid functional groups.

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15
Q

Amino acid + acids

A

Amino acid + acids -> salt + acid ion.

this is a reaction of the amine group

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16
Q

How many amino acids are there?

A

20.

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17
Q

Amino acid + alkalis

A

Amino acid + alkalis -> salt + water

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18
Q

Amino acid + alcohols

A

Amino acid + alcohols -> esters

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19
Q

Esterification

A

excess ethanol

and a small amount of sulphuric acid.

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20
Q

Define a zwitterion

A

It has no charge, because the H+ ion from the COOH group can move to the NH2 group and form a + and a - charge.

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21
Q

Define the isoelectric point

A

It is the pH at which the zwitterion is formed, and each amino acid has its own unique isolectric point.
If you have a pH above the isolelectric point, then you form a COO- ion.

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22
Q

Define an optical isomer

A

A chiral carbon with 4 different groups, making it a non-superimposable mirror image.

23
Q

What is glycine

A

It is the most simplest amino acid.

24
Q

Define a chiral centre

A

a Carbon atom that is attached to 4 different groups or atoms.

25
Q

How do you name amino acids

A

The COOH group is always more prioritised, so the Carbon attached to the COOH group is carbon 2.

26
Q

Define bi-functional

A

Can behave as an acid or an alkali as it has both functional groups.

27
Q

Define the racemix mixture

A

They have equal amounts of left and right handed enantiomers of a chiral molecule.

28
Q

Define a condensation polymer

A

Joining of monomers with the loss of a small molecule (usually water or HCl)

29
Q

What are the 2 ways in which a polyester can be made?

A
  1. 1 monomer containing 2 functional groups ( so It should have OH on one side and COOH on the other.)
  2. 2 monomers that have COOH on both sides or OH on both sides.
30
Q

What is a monomer that has 2 OH groups

A

a diol

31
Q

What is a monomer that has 2 COOH groups

A

A dicarboxylic acid

32
Q

Examples of a polyester made from 1 monomer

A
called PET (Polyethylene terephthalate)
it is made using benzene-1,4 di carboxylic acid and ethane-1,2 diol.
33
Q

How are polyamides formed

A

By a condensation reaction using a monomer that has both a carboxylic acid functional group (or acyl chloride) and an amine group functional group.
Or by 2 monomers which have 2 COOH functional groups and another which has 2 NH2 functional groups.

34
Q

What is an ester functional group

A

COO

35
Q

What is an amide functional group

A

COHN

36
Q

What is a monomer with 2 amine groups called

A

Diamine

37
Q

What is nylon made from?

A

Using hexanedioic acid and 1,6 diaminohexane
or
hexanedioyl chloride and 1,6 diaminohexane

38
Q

How do you name nylons

A

The first number is the number of Carbons in the amino group, and then the Carboxylic acid group one next.

39
Q

Acid hydrolysis of a polyester

A
Use H2SO4 (hot aqueous)/ H20
Products: Just the monomers
40
Q

Alkali hydrolysis of a polyester

A

Use NaOH/H2O

Products: alcohol and carboxylic-salt.

41
Q

Acid hydrolysis of a polyamide

A

Use H20 /H+

Products: NH3+ on the amines and a carboxylic acids.

42
Q

Alkali hydrolysis of a polyamide

A

Use NaOH/ H2O

Products: COO- Na+ and NH2 amines.

43
Q

Characteristics of an addition polymer

A

Contains a C=C bond in the monomer

Contains a backbone of a continuous chain

44
Q

Characteristics of a condensation polymer

A

2 monomers with 2 functional groups (on either sides)
1 monomer with 2 different functional groups
Polymer has ester/ amide linkages.

45
Q

C-N bond

A

It is polar.

The nitrogen is very electronegative, so it’s quite easy to break this C-N bond as it’s a weaker bond.

46
Q

Ammonia gas + HCl gas

A

It creates white smoke.

And NH4+Cl-

47
Q

Outline how an addition polymer is formed?

A

The pi-bond breaks and many molecules join together.

48
Q

Explain why xyz is considered to be a “degradable polymer”?

A

Because the C=O or the C-N bond can break and it is hydrolysed so that the polymer can be broken into its monomers.

49
Q

WHENEVER THERE IS ANYTHING ABOUT GREATER MELTING POINT?

A

ALWAYS INTERMOLECULAR FORCES!!

IS THERE ANY HYDROGEN BONDING? ANY LONDON FORCES? PERMANENT DIPOLE?!

50
Q

Why are secondary amines stronger bases than primary amines?

A

Because they have 2 alkyl groups that better stabilize the acid than primary amines, and so making it more basic.

51
Q

How do amines behave?

A

They behave as weak bases.

52
Q

State 2 disadvantages of synthesising something that makes a mixture of optical isomers?

Then 2 methods that are used to synthesis the only wanted optical isomer

A

One stereoisomer may have adverse side effects, and the cost of separating the stereoisomers can be quite high.

Methods: You have use natural chiral molecules or use enzymes or bacteria.

53
Q

Diazonium ion

A

A benzene ring where there is a N=-N attached to one Carbon atom.

54
Q

How can a polymer be broken down.

A

Either by hydrolysis or photodegradable