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OCR A Chemistry > 6.2 - Nitrogen Compounds, Polymers and Synthesis > Flashcards

6.2 - Nitrogen Compounds, Polymers and Synthesis Flashcards

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1
Q
A
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2
Q

How many different types of amines can we get? What are they?

A

3 types. Primary, Secondary and Tertiary

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3
Q

If we have a primary amine, how many hydrogen groups are attached to the nitrogen? Also, how many R groups are attached to the nitrogen?

A

2 hydrogens 1 R group

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4
Q

If we have a secondary amine, how many hydrogen groups are attached to the nitrogen? Also, how many R groups are attached to the nitrogen?

A

1 hydrogen 2 R groups

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5
Q

If we have a tertiary amine, how many hydrogen groups are attached to the nitrogen? Also, how many R groups are attached to the nitrogen?

A

NO hydrogens 3 R groups

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6
Q

Name the following primary amines: CH3NH2 CH3CH2CH2NH2

A

Methylamine Propylamine

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7
Q

Name the following secondary amines: CH3NHCH3 CH3CH2CH2NHCH3

A

N,N - Dimethylamine N,N- Methyl propanamine

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8
Q

Name the following tertiary amine: CH3NCH3CH3

A

Trimethylamine

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9
Q

Define the term base

A

A proton acceptor

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10
Q

Why can amines be regarded as bases?

A

Lone pair of electrons on the nitrogen atom that is able to accept protons.

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11
Q

When amines react with dilute acids, what is formed?

A

Ammonium salt

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12
Q

What is meant by aliphatic?

A

Straight chained compounds

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13
Q

Describe the preparation of aliphatic amines by substitution of haloalkanes

A

Aliphatic amines can be made by heating a haloalkane with an excess of ethanolic ammonia. Reagents = Haloalkane + Excess ethanolic ammonia Conditions = Sealed in a tube. Products = Aliphatic amine + Ammonia salt

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14
Q

Give a generic reaction equation for the formation of aliphatic amines by substitution of haloalkanes

A

RX + 2NH3 → RNH2 + NH4X Haloalkane + Ammonia → Aliphatic primary amine + Ammonium halide

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15
Q

In the process of preparing aliphatic amines, why is excess ethanolic ammonia used?

A

To prevent further substitution

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16
Q

In the process of preparing aliphatic amines, if we use excess haloalkane, what type of product do we get?

A

A quarternary ammonium salt e.g.

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17
Q

Describe the preparation of aromatic amines by reduction of nitroarenes

A

Aromatic amines are made by reducing a nitro compound such as nitrobenzene. Nitrobenzene is reduced by heating a nitrocompound with a reducing agent ( mix of conc. HCl and tin (Sn)) After 30 minutes has passed, we add a strong base such as NaOH to the salt produced from reducing nitrobenzene to get our aromatic amine. Reagents = Reducing agent (Mix of tin + conc. HCl) Conditions = 100 degrees celsius under reflux Products = Aromatic amine + 2H2O

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18
Q

Give the generic equation for the preparation of aromatic amines

A

Nitroarene + 6[H] → Phenyl amine + 2H2O Phenylamine is an aromatic amine

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19
Q

What is the general formula of amino acids?

A

RCH(NH2)COOH

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20
Q

Why can amino acids be regarded as amphoteric?

A

They have an acidic group as well as a basic group Acidic = COOH Basic = NH2

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21
Q

When an amino acid reacts with an alkali, what is produced?

A

A salt + Water Amino acid + Alkali → Salt + Water

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22
Q

When an alkali is added to an alpha amino acid, what happens to the COOH and the NH2 groups?

A

COOH becomes COO^-M+ where M is the metal from the alkali NH2 remains the same

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23
Q

What is meant by a zwitterion?

A

An ion with no overall charge because the positive and negative charges in the compound CANCEL each other out.

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24
Q

What is meant by the isoelectric point

A

The pH at which there is no net electrical charge on the amino acid

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25
Q

Describe the reaction of the carboxylic acid group of amino acids reacting in the formation of esters

A

The carboxylic acid group of amino acids can react with alcohol, in the presence of a strong acid catalyst (usually conc. sulfuric acid) under reflux to produce an ester and water Reagents = Amino acid + Alcohol Conditions = Reflux Product(s) = Ester + Water

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26
Q

Give the generic equation in the reaction between an amino acid and alcohol

A

Amino acid + Alcohol → Ester + Water

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27
Q

Describe the reaction of the amine group of amino acids with acids

A

When an amino acid reacts with an acid, the product formed is a SALT of the CONJUGATE ACID. In this reaction, the amino acid acts as a base an accepts the entire acid onto the amine group.

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28
Q

When an acid is added to an alpha amino acid, what happens to the COOH and the NH2 groups?

A

COOH stays the same NH2 changes to NH3^+Z^- Where Z is the group attached to the acid reactant

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29
Q

What is the functional group of amides?

A

RCON

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30
Q

What is a weak base, amines or amides?

A

Amides

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31
Q

How many types of amides can we get?

A

3 Primary, Secondary and Tertiary *You don’t need to know about tertiary amides

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32
Q

If we have a primary amide, how many hydrogen groups are attached to the nitrogen? Also, how many R groups are attached to the nitrogen?

A

2 hydrogen groups 1 R group

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33
Q

If we have a secondary amide, how many hydrogen groups are attached to the nitrogen? Also, how many R groups are attached to the nitrogen?

A

1 hydrogen group 2 R groups

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34
Q

How do we name primary amides?

A

Stem = Longest carbon chain (take off the e) Ending = Amide

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35
Q

What is a chiral carbon?

A

A carbon atom which has 4 different groups attached to it.

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36
Q

What do chiral carbons lead to ?

A

The possibility of optical isomerism

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37
Q

What are optical isomers?

A

Mirror images of each other, where no matter which way you turn them, they cannot be superimposed. They only occur if there’s a chiral carbon atom in a given molecule

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38
Q

What do optical isomers do? And in which directions?

A

Optical isomers rotate plane polarised light One optical isomer rotates plane polarised light in a clockwise direction, whilst the other optical isomer rotates it in an anticlockwise direct

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39
Q

When rotating light, optical isomers rotate it in…

A

The opposite direction but by the SAME amount

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40
Q

What must you do when drawing optical isomers?

A

Draw 3D bonds Draw the mirror line Reflect the isomers (as in switch the left and right molecules around)

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41
Q

Can some molecules have more than one chiral centre?

A

YES!

42
Q

How can we make a polyester?

A

Reacting a dicarboxylic acid with a diol forming ester links.

43
Q

How can we represent an ester link?

A

R-COO-R’ R and R’ can be the same aren’t often.

44
Q

Give the generic equation for the production of a polyester

A

Dicarboxylic acid + Diol → Polyester + Water

45
Q

In the production of polyesters, what is the waste product and where do the bonds that contribute in the production it come from?

A

Waste product is water. OH is lost from dicarboxylic acid H is lost from diol

46
Q

How can we make polyamides?

A

Reacting a dicarboxylic acid with a diamine forming amide links

47
Q

How can we represent an amide link?

A

CONH

48
Q

Give the generic equation for the production of a polyamide

A

Dicarboxylic acid + Diamine → Polyamide + Water

49
Q

What is meant by hydrolysis?

A

The process of breaking down a compound through the use of water.

50
Q

Because hydrolysis tends to be slow, we use an..

A

Acid or base

51
Q

For polyesters, what is faster, acidic hydrolysis or basic hydrolysis?

A

Basic

52
Q

For polyamides, what is faster, acidic hydrolysis or basic hydrolysis?

A

Acidic →

53
Q

If we hydrolyse a polyester under acidic conditions, what do we get?

A

An alcohol and a carboxylic acid

54
Q

If we hydrolyse a polyester under basic conditions, what do we get?

A

An alcohol and a dicarboxylate salt

55
Q

If we hydrolyse a polyamide under acidic conditions, what do we get?

A

A carboxylic acid and a di-salt of a diamine

56
Q

If we hydrolyse a polyamide under basic conditions, what do we get?

A

A diamine and the salt of a dicarboxylic acid

57
Q

Give the generic equation for the acidic hydrolysis of a polyester

A

Polyester + 2nH2O → Diol + Dicarboxylic acid

58
Q

Give the generic equation for the basic hydrolysis of a polyester

A

Polyester + 2nNaOH → Diol + Dicarboxylate salt

59
Q

Give the generic equation for the acidic hydrolysis of a polyamide

A

Polyamide + 2nH2O → Di-salt of amine + Dicarboxylic acid

60
Q

Give the generic equation for the basic hydrolysis of a polyamide

A

Polyamide + 2nNaOH → Diamine + Dicarboxylate salt

61
Q

How can we find the repeat unit from a given monomer for addition polymerisation?

A

Replace the double bond with a single bond Add a bond to each carbon, brackets and a n Repeat the monomer

62
Q

How can we find a repeat unit for a polyamide?

A

1) Draw the monomers next to each other 2) Remove an OH from the dicarboxylic acid and an H from the diamine 3) Join the C from the dicarboxylic acid with the N from the diamine to form an amide link 4) Take another OH and H off the ends of the moluecle 5) Draw brackets around it, and then there is your repeat unit

63
Q

How can we find a repeat unit for a polyester?

A

1) Draw the monomers next to each other 2) Remove an OH from the dicarboxylic acid and an H from the diol 3) Join the C from the dicarboxylic acid with the O from the diol to form an esterlink 4) Take another OH and H off the ends of the moluecle 5) Draw brackets around it, and then there is your repeat unit

64
Q

How do you find monomers from an addition polymerisation polymer chain?

A

Find repeat unit Remove empty bonds Replace the central carbon bond [C-C] with [C=C]

65
Q

How do you find monomers from an condensation polymer chain?

A

Find the amide (HN-CO) or ester (CO-O) link and break it down the middle Then add an H or an OH to bond ends of both molecules depending on what the groups at the end are Add Hs to O’s or N’s Add OH groups to carbon atoms

66
Q

What is a nucleophile?

A

An electron pair donor

67
Q

What is an electrophile?

A

An electron pair acceptor

68
Q

What is meant by nucleophilic substitution?

A

A reaction where a nucleophilic atom is subbed for another species.

69
Q

What is meant by nucleophilic addition?

A

A reaction where a nucleophile is added to a compound

70
Q

Is Cyanide an electrophile or nucleophile?

A

Nucleophile

71
Q

Describe the formation of CCN- by reaction of haloalkanes with CN

A

Reaction type = Nucleophilic substitution Reagents = Haloalkane + Ethanol + KCN/NaCN Conditions = Reflux Products = Nitrile + Halogen ion

72
Q

Give the generic equation for the formation of CCN- by reaction of haloalkanes with CN

A

RX + CN^- → R-C≡N + X^-

73
Q

In the formation of CCN- by reaction of haloalkanes with CN, why do we use ethanol rather than water?

A

If we use water, OH^- may act as the nucleophile rather than CN^- and so the carbon chain length will not increase.

74
Q

Describe the formation of CCN- by reaction of carbonyl compounds with HCN

A

Reaction type = Nucleophilic addition Reagents = Carbonyl compound + HCN Conditions = Products = Hydroxynitrile

75
Q

When referring to reactions, we must always talk about …..

A

Dipoles Charges Curly arrows Conditions Product Mechanism (if required)

76
Q

Why are nitriles useful?

A

Nitriles are useful because they can be converted into new functional groups. This is because the nitrile froup is very reactive.

77
Q

Give the 2 methods in which a nitrile could be reduced

A

Method 1 Using lithium aluminium hydride (LiAlH4) followed by some dilute acid. Method 2 (Catalytic hydrogenation) Using Hydrogen + Nickel cataltyst

78
Q

Give a generic equation for when a nitrile is reduced via LiAlH4 followed by dilute acid

A

RCH2C≡N + 4[H] → RCHCH2NH2

79
Q

Give a generic equation for when a nitrile is reduced via hydrogen and a nickel catalyst

A

RCH2C≡N + 2H2 → RCHCH2NH2

80
Q

Give all the details of the reduction of nitriles using H2 and a nickel catalyst

A

Reaction name = Catalytic hydrogenation Reagents = H2 and a Nickel Catalyst Conditions = High temperature and pressure Product = Primary amine

81
Q

When a nitrile is reduced, what is formed?

A

A primary amine

82
Q

Describe the reaction of nitriles by acidichydrolysis

A

If you reflux a nitrile with HCl, then the nitrile group hydrolyses to form a carboxylic acid. The other product is ammonium chloride. Reagents = Nitrile + HCl + H2O Conditions = Reflux Products = Carboxylic acid and ammonium chloride

83
Q

Give a generic equation for when a nitrile is hydrolysed under acidic conditions

A

RCH2C≡N + HCl + 2H2O → RCH2COOH + NH4Cl

84
Q

What is meant by Friedel-Crafts alkylation?

A

A reaction where any alkyl group is put onto a benzene ring using a haloalkane and a halogen carrier under anhydrous conditions. The resultant product is an alkylbenzene.

85
Q

Give the general equation for Friedel- Crafts alkylation

A

C6H6 + R-X → C6H5R + HX (Benzene) + (Haloalkane) → Alkylbenzene + Hydrogen halide Conditions: Reflux and a halogen carrier

86
Q

Give all the details of a Friedel-Crafts alkylation reaction

A

Reagents : A haloalkane and an anhydrous halogen carrier (catalyst) Conditions: Reflux in the presence of an anhydrous halogen carrier. (CATALYST) Products: Alkylbenzene + Hydrogen halide. Generation of electrophile :RX + FeX3 → R^+ + FeX4^- Regeneration of catalyst : H^+ + FeX4^- → FeX3 + HX

87
Q

Give the general equation for the generation of the electrophile in a alkylation reaction

A

RX + FeX3 → R^+ + FeX4^-

88
Q

Give the general equation for the regeneration of the catalyst for alkylation

A

H^+ + FeX4^- → FeX3 + HX

89
Q

What is meant by Friedel-Crafts acylation?

A

A reaction where any acyl group is put onto a benzene ring using an acyl chloride and an halogen carrier under anhydrous conditions. The resultant product is an phenylketone + HCl.

90
Q

Give the general equation for Friedel- Crafts acylation

A

C6H6 + RCOCl → C6H5COR + HCl (Benzene) + (Acyl Chloride) → (Phenylketone) + (HCl)

91
Q

Give all the details of a Friedel-Crafts acylation reaction

A

Reagents : An acyl chloride and an anhydrous halogen carrier Conditions: Reflux in the presence of an anhydrous halogen carrier. (CATALYST) Products: Phenylketone + Hydrochloric acid Electrophile: NO2+ Generation of electrophile: RCOCl + FeCl3 → FeCl4^- + R^+CO Regeneration of catalyst : H+ + FeCl4^- → FeCl3 + HCl

92
Q

Give the general equation for the generation of the electrophile in a acylation reaction

A

RCOCl + FeCl3 → FeCl4^- + R^+CO

93
Q

Give the general equation for the regeneration of the catalyst for acylation

A

H+ + FeCl4^- → FeCl3 + HCl

94
Q

Why do we use reflux?

A

To ensure that we don’t lose any volatile organic substances. This is because reflux prevents the evaporation of reagents

95
Q

Why do we use distillaion?

A

To separate substances with difference boiling points

96
Q

How does distillation work?

A

Distillation works by gently heating a mixture of substances. These substances will evaporate out in ORDER of increasing boiling point. If you know the boiling point of your pure product, you can use a thermometer to know where in will evaporate.

97
Q

What do we use filtration under reduced pressure to do?

A

Separate liquid impurities from solids

98
Q

Give the process of filtration under reduced pressure

A

Step 1) Connect thick-walled rubber tubing to vacuum source Step 2) Place Buchner/Hirsch funnel on top of the filter flask Step 3) Connect tubing with the vacuum source to the side arm of the filter flask and start suction Step 4) Put a piece of filter paper in the funnel (just enough to cover the holes) Step 5) Using the solvent (e.g. distilled water), wet the paper so it sticks over all holes Step 6) Pour reaction mixture into the funnel Step 7) Wash out the piece of equipment which contained the reaction mixture using a solvent over the funnel (Done to collect as much product as possible) Step 8) Rinse the solid on the filter paper with more solvent Step 9) Wait for some time and then turn off the suction Step 10) Tip contents of the funnel onto a watch glass

99
Q

What do we use crystallisation to do? (BENZOIC ACID PAG)

A

Purify impure solids

100
Q

Give the process of recrystallisatio

A

Step 1) Dissolve the impure solid in a minimum amont of hot solvent possible and filter Step 2) Cool solution by putting the filtrate in an ince bath Step 3) Collect purified product using vacuum filtrate Step 4) Wash with cold solvent/water and dry

101
Q

Why do we measure melting points?

A

To test for purity.

102
Q

Give the process of measuring melting points

A

Step 1) Place a few grains of organic product in a capillary tube Step 2) Insert the tube into a MP machine with a thermometer with a suitable range, Step 3) Turn on the machine and set the dial to 4 Step 4) Note the temperature when the crystals start to melt and when they are full liquidised

OCR A Chemistry (16 decks)

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