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Advanced Higher Chemistry Unit 3 > (b) synthesis > Flashcards

(b) synthesis Flashcards

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1
Q

What is the process of bond breaking known as?

A

Bond fission.

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2
Q

How many types of fission are there?

A

2

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3
Q

What are the names of the two types of fission?

A

Homolytic and hetrolytic.

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4
Q

What does homolytic fission result in?

A

The formation of 2 neutral free radicals.

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5
Q

Why does homolytic fission result in free radicals?

A

When each atom retains one electron from the sigma covalent bond and the bond breaks evenly.

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6
Q

What type of bond is usually broken when homolytic fission occurs?

A

Non-polar covalent bonds.

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7
Q

Why do reactions involving homolytic fission result in mixtures which are unsuitable for organic synthesis?

A

The resulting mixtures are formed of very complex mixtures of products.

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8
Q

What does heterolytic fission result in the creation of?

A

Two oppositely charged ions.

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9
Q

Why does heterolytic fissions create ions?

A

One atom retains both electrons from the sigma covalent bond and the bond breaks unevenly.

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10
Q

What type of bond is usually broken when heterolytic fission occurs?

A

Polar covalent bonds.

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11
Q

Why are the products of reactions involving heterolytic fission much better suited for organic synthesis?

A

There tends to be far fewer products than reactions involving homolytic fission.

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12
Q

What are the attacking groups involved in heterolytic fission called?

A

Nucleophiles and electrophiles.

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13
Q

What are nucleophiles?

A

Negatively charged ions or neutral molecules that are electron rich.

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14
Q

What is an example of a nucleophile?

A

Chlorine ion, bromine ion, water, e.c.t.

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15
Q

What are nucleophiles attracted to?

A

Atoms bearing a partial or full positive charge.

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16
Q

What are nucleophiles capable of doing?

A

Donating an electron pair to form a new covalent bond.

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17
Q

What are electrophiles?

A

Positively charged ions or neutral molecules which are electron deficient.

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18
Q

What is an example of an electrophile?

A

Hydrogen ion, nitrogen oxide e.c.t.

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19
Q

What are electrophiles attracted to?

A

Atoms bearing a partial or full negative charge.

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20
Q

What are electrons capable of doing?

A

Accepting an electron pair to form a new covalent bond.

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21
Q

What is a haloalkane?

A

Substituted alkanes in which one or more of the hydrogen atoms is replaced with a halogen atom.

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22
Q

How many halogen atoms are in a monohaloalkane?

A

1

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23
Q

Can monohaloalkanes take part in elimination reactions?

A

Yes.

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24
Q

What must be present for monohaloalkanes to undergo elimination reactions?

A

A strong base.

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25
Q

Give an example of a strong base.

A

Potassium or sodium hydroxide in ethanol.

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26
Q

What other reactions can monohaloalkanes take part in?

A

Nucleophilic substitution.

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27
Q

If a monohaloalkane undergoes nucleophilic substitution with an aqueous alkali what is formed?

A

Alcohol.

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28
Q

If a monohaloalkane undergoes nucleophilic substitution with a alcoholic alkoxides what is formed?

A

Ether.

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29
Q

If a monohaloalkane undergoes nucleophilic substitution with ethanolic cyanide what is formed?

A

Nitriles.

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30
Q

What happens to the chain length when a monohaloalkane undergoes nucleophilic substitution to become a nitrile?

A

The chain length increases by one carbon atom.

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31
Q

What can happen to this nitrile?

A

It can be hydrolysed to become a carboxylic acid.

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32
Q

What is reacted with a mono halo alkane to form an alcohol?

A

aqueous alkali.

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33
Q

What is reacted with a mono halo alkane to form ethers?

A

alcoholic alkoxides.

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34
Q

What is reacted with a mono halo alkane to form nitriles?

A

Ethanolic cyanide.

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35
Q

What is SN1 substitution?

A

A nucleophilic substitution reaction with one species in the rate determining step and occurs in a minimum of two steps via a trigonal planar carbocation intermediate.

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36
Q

What is SN2 substitution?

A

A nucleophilic substitution reaction with two species in the rate determining stipend occurs in a single step via a single 5 centred trigonal bipyramidal transition state.

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37
Q

What types of molecules undergo SN1 substitution?

A

Tertiary and sometimes secondary haloalkanes.

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38
Q

Why do only tertiary and sometimes secondary haloalkanes undergo SN1 substitution?

A

Because there is no room for a nucleophile to attack the central carbon.

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39
Q

What is this blocking effect known as?

A

Steric hindrance.

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40
Q

what types of molecules undergo SN2 substitution?

A

Primary and sometimes secondary haloalkanes.

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41
Q

Why can only primary and sometimes secondary haloalkanes undergo SN2 substitution?

A

Because there is less steric hinderance.

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42
Q

Where does the nucleophile attack from in SN2?

A

The opposite side to the halogen.

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43
Q

What type of molecule undergoes substitution to form alcohols?

A

Alkanes.

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44
Q

How else can alcohols be prepared?

A

alkenes by acid-catylised hydration

the reduction of aldehydes and ketones using a reducing agent.

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45
Q

What is an example of a reducing agent which would allow the reduction of aldehydes and ketones into alcohols to take place?

A

Lithium aluminium hydride.

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46
Q

What does an alcohol dehydrate to form?

A

Alkenes.

47
Q

What is used to dehydrate alcohols to produce alkenes?

A

Aluminium oxide
Concentrated sulphuric acid
Concentrated phosphoric acid.

48
Q

How are alkenes formed from alcohols?

A

Through dehydration with aluminium oxide, concentrated sulphuric acid, or concentrated phosphoric acid.

49
Q

What does a primary alcohol oxidise to form?

A

An aldehyde.

50
Q

What do aldehydes oxidise to form?

A

Carboxylic acids.

51
Q

What do secondary alcohols oxidise to form?

A

Ketones.

52
Q

What are alcohols oxidised with to form aldehydes and ketones?

A

Acidified potassium permanganate
Acidified dichromate
Hot copper (II) oxide.

53
Q

How are aldehydes and ketones formed from alcohols?

A

Through oxidation of a primary, to become an aldehyde, or secondary, to become a ketone, alcohol with acidified potassium permanganate, acidified dichromate, or hot copper (II) oxide.

54
Q

When alcohols react with some reactive metals what is formed?

A

alcoholic alkoxides.

55
Q

What reactive metals react with alcohols to form alcoholic alkoxides?

A

Potassium or Sodium.

56
Q

What can alcoholic alkoxides then react with to produce a different molecule?

A

Monohaloalkanes to form ethers.

57
Q

How are alcoholic alkoxides produced from alcohol?

A

Alcohols react with some reactive metals such as sodium or potassium.

58
Q

Alcohols react with carboxylic acids to form what?

A

Esters.

59
Q

What are alcohols and carboxylic acids reacted with to form esters?

A

Sulphuric acid

Phosphoric acid

60
Q

What does phosphoric and sulphuric acid act as in the reaction between an alcohol and a carboxylic acid?

A

A catalyst.

61
Q

How are esters produced from alcohols?

A

By reacting alcohols with carboxylic acids using concentrated sulphuric acid or concentrated phosphoric acid as a catalyst.

62
Q

What is a faster way to create esters without using a catalyst?

A

Reacting alcohols with acid chlorides.

63
Q

What do hydroxyl groups make alcohols?

A

Polar.

64
Q

What does polar bonds give rise to?

A

Hydrogen bonding.

65
Q

What can hydrogen bonding be used to explain?

A

The properties of alcohols.

66
Q

What can ethers be regarded as?

A

substituted alkanes.

67
Q

How are ethers named?

A

By adding alkoxy to prefix the longest carbon chain.

68
Q

How can ethers be produced?

A

Through nucleophilic substitution reaction by reacting a monohaloalkane with an alkoxide.

69
Q

Do ethers have higher or lower boiling points compared to the isomeric alcohols?

A

Lower.

70
Q

Why do ethers have lower boiling points compared to the corresponding isomeric alcohols?

A

Lack of hydrogen bonding in ethers.

71
Q

Are ethers soluble or insoluble in water?

A

The first two ethers are soluble in water, however larger ethers are insoluble due to their increased molecular size.

72
Q

Why are ethers commonly used as solvents?

A

They are relatively inert and will dissolve many organic compounds.

73
Q

How can alkenes be prepared from alcohols?

A

Dehydration of alcohols using aluminium oxide, concentrated sulphuric acid or concentrated phosphoric acid.

74
Q

How else can alkenes be prepared?

A

Base-induced elimination of hydrogen halides from monohaloalkanes.

75
Q

Alkenes take part in electrophilic addition with what?

A

Hydrogen
Hydrogen halides
Water

76
Q

What is formed when alkenes undergo electrophilic addition with hydrogen in the presence of a catalyst?

A

Alkanes.

77
Q

What is produced when alkenes undergo electrophilic addition with hydrogen not in the presence of a catalyst?

A

Dihaloalkanes.

78
Q

What is formed when alkenes undergo electrophilic addition with hydrogen halides?

A

Monohaloalkanes.

79
Q

What is produced when alkenes undergo electrophilic addition with water using an acid catalyst?

A

Alcohols.

80
Q

What is required for alkenes to produce alcohols?

A

Acid catalyst.

81
Q

What does Markovnikovs’ rule state?

A

When a hydrogen halide or water is added to an unsymmetrical alkene, the hydrogen atom becomes attached to the carbon with the most hydrogen atoms attached to it already.

82
Q

What can Markovnikovs’ rule predict?

A

Major and minor products.

83
Q

How are carboxylic acids produced from primary alcohols?

A

Oxidation using potassium permanganate, acidified potassium dichromate, and hot copper (II) oxide.

84
Q

How are carboxylic acid produced from aldehydes?

A

Oxidation using acidified permanganate, acidified dichromate, Fehling’s solution, or Tollens’ reagent.

85
Q

How are carboxylic acids produced from nitriles, esters or amides?

A

Hydrolising.

86
Q

What is formed when carboxylic acids react with metals or bases?

A

Salts.

87
Q

How are salts formed from carboxylic acids?

A

By reacting carboxylic acids with metals or bases.

88
Q

How are Esthers formed from carboxylic acids?

A

Condensation reactions with alcohol.

89
Q

What must be present for the condensation reaction with alcohol for Esthers to be made?

A

Concentrated sulphuric acid

Concentrated phosphoric acid.

90
Q

When carboxylic acids react with amines what is formed?

A

Alkyl ammonium salts.

91
Q

How are alkyl ammonium salts created?

A

Through the heating of amides.

92
Q

What is formed when carboxylic acids are reduced with lithium ammonium hydride?

A

Primary alcohols.

93
Q

What must be present for carboxylic acids to be reduced into primary alcohols?

A

Lithium ammonium hydride.

94
Q

What amines organic derivatives of?

A

Ammonia.

95
Q

How do amines and ammonia differ?

A

One or more of the hydrogen atoms has been replaced with an alkyl group.

96
Q

When amines react with acids what is formed?

A

Salts.

97
Q

What kind of amines show hydrogen bonding?

A

Primary and secondary amines.

98
Q

What kinds of amines have the highest melting and boiling points?

A

Primary and secondary.

99
Q

Can all amines hydrogen bond with water?

A

Yes.

100
Q

Why are smaller amines more soluble in water?

A

Hydrogen bonding.

101
Q

What makes amines similar to ammonia?

A

They are both weak bases.

102
Q

What happens to both amines and ammonia in water?

A

They dissociate.

103
Q

How are hydroxide ions produced from amines and ammonia in water?

A

The nitrogen atom has a lone pair of electrons which can accept a proton from water producing hydroxide ions.

104
Q

What is the simplest member of the aromatic hydrocarbons?

A

Benzene.

105
Q

What is benzenes formula?

A

C6H6

106
Q

What is the stability of benzene due to?

A

The delocalisation of electrons in the conjugated system.

107
Q

Why does benzene not take part in any addition reaction?

A

The presence of delocalised electrons.

108
Q

How can bonding in benzene be described?

A

Sp2 hybridisation, sigma and pi bonds, and electron delocalisation.

109
Q

What is it called when in a benzene ring one hydrogen atom has been substituted by another group?

A

The phenyl group.

110
Q

What is the formula of the phenyl group?

A

C6H5.

111
Q

How does benzene undergo halogenation?

A

The addition of a halogen using aluminium chloride, or iron(III) chloride for chlorination, and aluminium bromide or iron (III) bromide for bromination.

112
Q

How does benzene undergo alkylation?

A

By reaction of a haloalkane using aluminium chloride.

113
Q

How does benzene undergo nitration?

A

Using concentrated sulphuric acid and concentrated nitric acid.

114
Q

How does benzene undergo sulfonation?

A

Using concentrated sulphuric acid.

Advanced Higher Chemistry Unit 3 (4 decks)

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