Chapter 27- Amines, Amino Acids and Polymers Flashcards

1
Q

What is the difference between an aliphatic amine and an aromatic amine ?

A
  • Aliphatic - Nitrogen is attached to at least one straight or branched carbon chain
  • Aromatic - Nitrogen is attached to an aromatic ring
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2
Q

What do amines often behave as?

A

Bases

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3
Q

How do amines behave as bases?

A

Nitrogen donates electron pair to H+

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4
Q

For the formation of primary amines, what is reacted together in the two steps?

A
  • Haloalkane and salt
  • Salt and sodium hydroxide
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5
Q

In primary amine formation, what is in excess and why?

A
  • Ammonia is in excess
  • Prevents product from reacting with more of the haloalkane
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6
Q

In primary amine formation, what is the purpose of ethanol?

A

It prevents substitution of haloalkane by water to produce alcohols

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7
Q

What are the two steps of forming a secondary amine from a primary amine?

A
  • Primary amine + CH3Br and ethanol as solvent
  • Salt product + NaOH forms secondary amine
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8
Q

How is phenylamine made from nitrobenzene?

A
  • Nitrobenzene is heated under reflux with tin and HCl to form ammonium salt
  • Ammonium salt is reacted with NaOH to produce phenylamine
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9
Q

What do tin and HCl act as in formation of phenylamine from nitrobenzene?

A

Reducing agents

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10
Q

What is an amino acid ?

A

An organic compound that contains both an amine and a carboxylic acid group

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11
Q

What do amino acids react similarly to ?

A

Amines and carboxylic acids

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12
Q

What properties does the amine group have ?

A

It is basic

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13
Q

What does the amine group react with ?

A

It reacts with an acid to make a salt

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14
Q

What does the carboxylic acid group react with ?

A
  • Reacts with an alkali to form a salt
  • Reacts with an alcohol to form an ester
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15
Q

Amino acid + aqueous alkali reaction

A

Forms a salt and water

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16
Q

Can amino acids undergo esterification ?

A

Yes

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17
Q

How do amino acids undergo esterification ?

A
  • Heating with an alcohol
  • In the presence of concentrated sulfuric acid
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18
Q

What do the acidic conditions in esterification lead to for an amino acid ?

A

The acidic conditions protonate the basic amine group of the ester

19
Q

What is a zwitterion ?

A

It is when there is both a positive and negative charge present in the structure

20
Q

Why does a zwitterion arise in an amino acid ?

A

The basic amine group can accept a proton from the carboxylic acid group

21
Q

What is the charge of zwitterions ?

A

It is neutral

22
Q

What is the isoelectric point of a zwitterion ?

A
  • The pH at which the zwitterion is formed
  • Each amino acid has its own unique isoelectric point
23
Q

What happens when the amino acid is added to a solution with a pH greater than its isoelectric point ?

A

The amino acid behaves as an acid and loses a proton

24
Q

What happens when the amino acid is added to a solution with a pH less than its isoelectric point ?

A

The amino acid behaves as a base and gains a proton

25
Q

How are amides formed ?

A

Amides are the products of reactions of acyl chlorides with ammonia and amines

26
Q

What is optical isomerism ?

A

It is a type of stereoisomerism

27
Q

Where is optical isomerism found ?

A

In molecules that have a chiral centre

28
Q

What is a chiral centre ?

A

It is a carbon that is attached to four different atoms or group of atoms

29
Q

What does the presence of a chiral carbon atom lead to ?

A
  • It leads to the existence of two non-superimposable mirror image structures
  • These are known as enantiomers (optical isomers)
30
Q

What do optical isomers have in common ?

A

Same physical properties

31
Q

What are the two monomer types that form polyesters?

A
  • Diols
  • Dicarboxylic acids
32
Q

How can polyesters be formed from one monomer?

A
  • One end has an alcohol group
    • One end has a carboxyl group
33
Q

What is condensation polymerisation?

A
  • Joining of monomers with loss of a small molecule, usually water or HCl
  • Two different functional groups are needed
34
Q

How can polyamides be formed from just one monomer?

A

Amino acids contain a carboxylic acid and an amine group

35
Q

How can polyamides be formed from two monomers?

A
  • Diamine
  • Dicarboxylic acid
36
Q

What is the common name for polyamides made from two monomers?

A

Nylon

37
Q

What is required to undergo acid hydrolysis?

A
  • Excess HCl
  • Water
38
Q

What is formed from polyester undergoing acid hydrolysis?

A
  • Diol
  • Dicarboxylic acid
39
Q

What is formed from acid hydrolysis of polyamide?

A
  • Diammonium salt
  • Dicarboxylic acid
40
Q

What is required to undergo base hydrolysis?

A

Excess NaOH

41
Q

What is formed from polyester undergoing base hydrolysis?

A
  • Diol
  • Salt of dicarboxylic acid
42
Q

What is formed from base hydrolysis of polyamide?

A
  • Diamine
  • Salt of dicarboxylic acid
43
Q

How does addition polymerisation differ from condensation polymerisation with monomers?

A
  • Addition - Monomer contains C=C bond
  • Condensation - Two monomers with two functional groups or one monomer with two different functional groups
44
Q

How does addition polymerisation differ from condensation polymerisation with backbone?

A
  • Addition - Backbone of polymer is -C-C- bond
  • Condensation - Polymer back bone contains ester or amide group