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A-Level Edexcel Chemistry > Chapter 6 - Organic chemistry I (L) > Flashcards

Chapter 6 - Organic chemistry I (L) Flashcards

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1
Q

What are hydrocarbons?

A

Compounds that contain only carbon and hydrogen

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2
Q

What are saturated hydrocarbons?

A

Hydrocarbons with the maximum amount of hydrogens possible

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3
Q

What are unsaturated hydrocarbons?

A

Hydrocarbons without the maximum amount of hydrogens possible

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4
Q

What does any compound ending in -ate contain?

A

Oxygen

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5
Q

What does a double bond always mean in terms of saturation?

A

The compound is unsaturated

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6
Q

What does all single bonds in a compound mean in terms of saturation?

A

The compound is saturated

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7
Q

What is a multiple bond?

A

Two or more covalent bonds between two atoms

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8
Q

What are displayed formulae?

A

They show every bond and atom separately

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9
Q

What are structural formulae?

A

Don’t show individual atoms, and can show bonds but can not. For example:
CH3CH2CH3 and CH3-CH2-CH3 are both structural formula of propane

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10
Q

What are skeletal formulae?

A

Each dot represents a carbon atom, and the line between represents the bond between them

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11
Q

What is the molecular formula?

A

Shows the actual number of atoms in a molecule

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12
Q

What is the empirical formula?

A

Shows the numbers of each atom in the simplest whole number ratio

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13
Q

What is a functional group?

A

An atom or group of atoms in a molecule that is responsible for its chemical reactions

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14
Q

What is a homologous series?

A

A group of compounds with the same functional group and general formula, which differ by CH2 from the next member

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15
Q

What is the general formula of alkanes?

A

Cn H2n+2

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16
Q

What is the general formula of alkenes?

A

Cn H2n

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17
Q

What is the general formula of halogenealkanes?

A

Cn H2+1 X (X = any halogen)

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18
Q

What is the general formula of alcohols?

A

Cn H2n+1 OH

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19
Q

What is the equation for the complete combustion of methane?

A

CH4 + 2O2 -> CO2 + 2H2O

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20
Q

What is nomenclature?

A

The rules of naming molecules

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21
Q

How do I revise nomenclature?

A

Read through the rules and then do practice questions

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22
Q

What are structural isomers?

A

Compounds with the same molecular formula but different structural formula

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23
Q

What are the two types of structural isomerism?

A

Chain and position isomerism

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24
Q

What is chain isomerism?

A

When molecules have different carbon chains e.g. Butane and Methyl-propane

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25
Q

What is position isomerism?

A

When molecules have the same functional group attached in different places e.g. Propan-1-ol and Propan-2-ol

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26
Q

Can both position and chain isomerism be present simultaneously?

A

Yes

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27
Q

What is stereoisomerism?

A

When molecules have the same molecular and structural formula, however a different spatial arrangement

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28
Q

What type of isomerism does geometric isomerism come under?

A

Stereoisomerism

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29
Q

What is geometric isomerism also known as?

A

Cis-trans isomerism

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30
Q

Where can geometric isomers occur and not occur?

A

It can occur in alkenes, but not in alkanes

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31
Q

Why can geometric isomers occur in alkenes but not alkanes?

A

Because the presence of C=C leads to restricted rotation, whereas in alkanes the atoms can rotate freely, without restriction

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32
Q

What is cis isomerism?

A

When the two alkyl groups are on the same side of the C=C

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33
Q

What is trans isomerism?

A

When the two alkyl groups are on opposite sides of the C=C

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34
Q

When does cis-trans notation not work and why is this the case?

A

When there are 4 different groups, because the idea of two identical groups being in a cis- or trans- arrangement does not work, as there are not two groups that are the same

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35
Q

In E-Z notation how do you decide which two atoms are the highest priority?

A

The atom with the highest atomic number on the left of the double bond, and the atom with the highest atomic number on the right of the double bond are the two atoms with the highest priority

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36
Q

What are geometric isomers?

A

Compounds containing a C=C, with the same molecular and structural formula, but with the atoms attached at different positions

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37
Q

What is a locant?

A

A number used to indicate which carbon atom in the chain an atom or group is attached to- e.g. in 2-methyl-propane, the methyl group would be attached to the second carbon (2 is the locant)

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38
Q

In E-Z notation, once you have found the two atoms with the highest priority, what do you do?

A

See whether the two atoms with the highest priority are opposite each other or not- if they are you have an E-isomer, if not you have a Z-isomer

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39
Q

Z meaning (German)

A

Zusammen = Together

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40
Q

E meaning (German)

A

Entgegen = Opposite

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41
Q

What are most compounds in crude oil and natural gas?

A

Alkanes

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42
Q

What are the 3 main processes used to convert crude oil into fuels?

A
  • Cracking
  • Reforming
  • Fractional distillation
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43
Q

What is fractional distillation?

A

The process used to separate a liquid into fractions by boiling and condensing

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44
Q

As you go down in fractional distillation, what 4 trends will you see?

A 
As you go down, it will be 
- hotter
and the molecules will be
- longer chains
- less flammable
- more viscous
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45
Q

In fractional distillation, where will you find the compounds with the highest boiling points?

A

At the bottom

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46
Q

What happens to the dissolved gases in crude oil during fractional distillation?

A

They rise to the top of the column without condensing

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47
Q

What is cracking?

A

The breakdown of longer chain molecules into smaller ones by heating with a catalyst

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48
Q

Why is the cracking of hydrocarbons important?

A

Because the demand for longer chain hydrocarbons is much less than the demand for shorter chain hydrocarbons, therefore cracking is used to turn longer chain into shorter chain hydrocarbons

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49
Q

What is the process of cracking hydrocarbons?

A

Longer chain hydrocarbons are passed through a heated catalyst, normally zeolite. This causes larger molecules to break up into at least 2 smaller molecules

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50
Q

What is the catalyst usually used in the cracking of hydrocarbons?

A

Zeolite, which is made up of aluminium, oxygen and silicon

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51
Q

Give one good example of cracking of hydrocarbons

A

Decane -> Octane + Ethene

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52
Q

What is the key difference between fractional distillation and cracking?

A

Fractional distillation involves separating existing compounds, not making new ones in a chemical reaction, which is what cracking does

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53
Q

What is reforming?

A

The conversion of straight-chain hydrocarbons into branched or cyclic hydrocarbons

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54
Q

Why is reforming used?

A

Hydrocarbons with a straight-chain burn less efficiently than cyclic or branched chains, which will then burn more smoothly in an engine

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55
Q

What is the process of reforming hydrocarbons?

A

Straight-chain hydrocarbons are heated with a catalyst, normally platinum.

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56
Q

What catalyst is usually used in reforming hydrocarbons?

A

Platinum

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57
Q

Give one good example of reforming of hydrocarbons

A

Pentane -> Cyclopentane + H2

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58
Q

What are the main products of the complete combustion of alkanes?

A

CO2 and H2O

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59
Q

What are the main possible products of the incomplete combustion of alkanes?

A

CO, Carbon particulates and unburned hydrocarbons

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60
Q

How are oxides of sulphur produced?

A

During the combustion of alkanes, sulfur impurities in the alkane form sulfur dioxide, and then can react with the atmosphere to form sulfur trioxide

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61
Q

What is the problem with oxides of sulfur?

A

They are acidic, and so when they dissolve in water in the atmosphere, they form sulfurous acid and sulfuric acid. This can cause environmental damage

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62
Q

How are oxides of nitrogen formed?

A

Very high temperatures, such as around spark plugs in cars, can cause the nitrogen molecules in the air to react with oxygen molecules

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63
Q

What are oxides of nitrogen represented by?

A

The formula NOx

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64
Q

What are the main oxides of nitrogen?

A

NO and NO2

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65
Q

What is the problem with nitrogen dioxide?

A

It is acidic, and so when it dissolves in water in the atmosphere, it forms nitrous acid and nitric acid. This can cause environmental damage

66
Q

What is complete combustion?

A

When all the atoms in the fuel are fully oxidised

67
Q

What is incomplete combustion?

A

When some of the atoms in the fuel are not fully oxidised

68
Q

What three pollutants do three way converters remove?

A

Carbon monoxide, unburned hydrocarbons and oxides of nitrogen

69
Q

What three products are formed after going through three way catalytic converters?

A

Nitrogen, Water and Carbon dioxide

70
Q

What always happens to the hydrogen atoms during combustion (including incomplete)?

A

They are all completely oxidised to water

71
Q

What are biofuels?

A

Fuels obtained from living matter that has died recently

72
Q

What are renewable energy sources?

A

Sources that can be continuously replaced

73
Q

What are non renewable energy sources?

A

Sources that are not being replenished, except over geological timescales

74
Q

What is biodiesel?

A

A fuel made from vegetable oils obtained from plants

75
Q

What are bioalcohols?

A

Fuels made from plant matter, often using enzymes or bacteria

76
Q

What is a mechanism?

A

The sequence of steps in an overall reaction. Each step shows what happens to the electrons involved in bond breaking and forming

77
Q

What is homolytic fission?

A

The breaking of a covalent bond, in which each of the bonding electrons leaves with one species, forming two radicals e.g. Cl2 -> Cl. + Cl.

78
Q

What is a radical?

A

A species that contains an unpaired electron

79
Q

In radical mechanisms, what is the initiation step?

A

When one molecule becomes two radicals e.g. Cl2 -> Cl. + Cl.

80
Q

In radical mechanisms, what is the propagation step?

A

When a molecule and a radical become a different radical and molecule (there are two reactions in this step)

81
Q

What normally causes the initiation step?

A

Bond breaking caused by UV radiation

82
Q

In radical mechanisms, what is the termination step?

A

When two radicals become one molecule

83
Q

When are sigma bonds formed between carbon atoms in alkenes?

A

When sp2 hybrid orbitals overlap axially/head on

84
Q

When are pi bonds formed in alkenes?

A

When p orbitals overlap laterally/sideways

85
Q

Which are stronger, sigma or pi bonds?

A

Sigma bonds are stronger than pi bonds

86
Q

Why are sigma bonds stronger than pi bonds?

A

Because in pi bonds the negative electrons are further away from the positive nucleus of the carbon atoms than the sigma bonds, meaning the electrostatic attraction is weaker, and the electrons are more available and ready to react

87
Q

What are the two electron orbitals?

A

p and s orbitals

88
Q

What is hydrogenation?

A

An addition reaction in which hydrogen is added to an alkene e.g C2H4 (ethene) + H2 -> C2H6 (ethane)

89
Q

What is required for the hydrogenation of ethene to occur?

A

Heat and a nickel catalyst

90
Q

What is hydration?

A

An addition reaction in which water is added to an alkene (however think of it as adding a H and an OH)
e.g C2H4 (ethene) + H2O -> C2H5OH (ethanol)

91
Q

What is required for the hydration of ethene to occur?

A

Steam and a phosphoric acid catalyst (H3PO4). The water must be in gaseous form (steam)

92
Q

What is halogenation?

A

An addition reaction in which a halogen (e.g. Cl2 or Br2) is added to an alkene (remember it will always be two halogens being added, as they always go around in pairs)

93
Q

What is a hydrogen halide?

A

Hydrogen with a halogen e.g. HBr or HCl

94
Q

Why can hydrogen halides not be used to test for a double bond?

A

Because the reactants and products are both colourless

95
Q

What is the test for a double bond and what would you expect to see?

A

Add bromine and if a double bond is present, the solution will be decolourised (turn from orange to colourless)

96
Q

What catalyst is required for the hydration of ethene?

A

H3PO4

97
Q

What is a diol?

A

A compound containing two OH groups

98
Q

During oxidation to diols, what supplies the oxygen?

A

Potassium manganate (KMnO4)

99
Q

What does [O] mean?

A

It represents oxygen supplied by an oxidising agent

100
Q

How can you use oxidation to diols to test for the presence of a double bond?

A

If a double bond is present, the solution will change from purple to colourless

101
Q

What is an electrophile?

A

An electron pair acceptor

102
Q

What does a curly arrow represent?

A

The movement of a pair of electrons

103
Q

What is the symbol for slightly (e.g. slightly positive)

A

Delta (weird looking d)

104
Q

What is heterolytic fission?

A

The breaking of a covalent bond so that both bonding electrons are taken by one atom

105
Q

What is a carbocation?

A

Carbon left positive during the transition stage

106
Q

What are primary, secondary and tertiary carbocations?

A 
Primary= carbon attached to one carbon
Secondary= carbon attached to two other carbons
Tertiary= carbon attached to three other carbons
107
Q

One use of inert compounds

A

Non-stick coating

108
Q

What does it mean to be inert?

A

Unreactive

109
Q

What are elimination reactions?

A

A reaction in which a molecule loses atoms attached to adjacent carbon atoms, forming a C=C bond

110
Q

What is a compound with three alcohols groups called?

A

A triol

111
Q

What is a primary alcohol?

A

An alcohol group which is connected to a carbon attached to one other carbon

112
Q

What is a secondary alcohol?

A

An alcohol group which is connected to a carbon attached to two other carbons

113
Q

What is a tertiary alcohol?

A

An alcohol group which is connected to a carbon attached to three other carbons

114
Q

What are the products of the complete combustion of alcohols?

A

H2O and CO2

115
Q

What is halogenation?

A

Where the hydroxyl group in an alcohol is replaced by a halogen

116
Q

Can you add a halogen to an alcohol?

A

Yes, but a different method is required for each halogen

117
Q

What are the reaction requirements for the chlorination of an alcohol?

A
  • Phosphorus(V) chloride

- Mixture does not need heating

118
Q

What are the two (inorganic) products of the chlorination of an alcohol (name and formula)?

A 
Phosphorus oxychloride (POCl₃)
Hydrogen chloride (HCl)
119
Q

How can tertiary alcohols be chlorinated in a different way to primary and secondary?

A

Shake the alcohol with concentrated hydrochloric acid at room temperature

120
Q

What are the reaction requirements for the bromination of an alcohol?

A
  • Mixture of potassium bromide and 50% concentrated sulfuric acid
  • Warm mixture with alcohol
121
Q

What are the three (inorganic) products of the bromination of an alcohol?

A
  • Hydrogen bromide (HBr)
  • Potassium hydrogensulfate (KHSO4) or Potassium sulfate (K2SO4)
  • Water (H2O)
122
Q

In the bromination of an alcohol, what are the equations of the two reactions occuring?

A

KBr + H2SO4 –> K(H)SO4 + HBr

Alcohol + HBr –> Halogenoalkane + H2O

123
Q

What are the reaction requirements for the iodination of an alcohol?

A
  • Red phosphorus and Iodine

- Mixture (including alcohol) is heated under reflux

124
Q

What are the two (inorganic) products of the iodination of an alcohol?

A
  • Phosphorus iodide (PI3)

- Phosphonic acid (H3PO3)

125
Q

What is a dehydration reaction?

A

A reaction that results in the removal of a hydroxyl group and a single hydrogen atom from an adjacent carbon in an alcohol molecule, forming a C=C bond

126
Q

Why is the dehydration of butan-2-ol special?

A

There are three possible products:

  • but-1-ene
  • two isomeric forms of but-2-ene
127
Q

What is produced when a secondary alcohol is oxidised?

A

A ketone

128
Q

What is produced when a primary alcohol is oxidised?

A

An aldehyde, then with oxidation of the aldehyde a carboxylic acid is formed

129
Q

What are the reaction conditions for the oxidation of alcohols?

A
  • Heat

- Oxidising agent

130
Q

What is the common reagent in oxidising alcohols?

A

A mixture of potassium dichromate and excess of dilute sulfuric acid

131
Q

What apparatus is used to obtain ketones or carboxylic acids in oxidising alcohols?

A

Heating under reflux

132
Q

What apparatus is used to obtain aldehydes in oxidising alcohols?

A

Distillation with addition

133
Q

How does distillation with addition in the oxidation of alcohols work?

A
  • Oxidising agent heated
  • Alcohol slowly added to oxidising agent
  • When aldehyde is formed, it immediately distils off (due to much lower boiling point) and is collected in reciever
134
Q

What is formed when you add water (hydrolyse) to a halogenoalkane?

A

An alcohol

135
Q

What are the reaction conditions for the hydrolysis of a halogenoalkane?

A
  • Warm
136
Q

What is formed when you add KOH to a halogenoalkane?

A

An alcohol

137
Q

What are the reaction conditions for the addition of KOH to a halogenoalkane to form an alcohol?

A
  • Heat under reflux
138
Q

What is an ethanolic solution?

A

A solution in which ethanol is the solvent

139
Q

What are the reaction conditions for addition of KCN to a halogenoalkane?

A
  • Heat under reflux

- Ethanolic solvent

140
Q

What are the reaction conditions for addition of NH3 to a halogenoalkane?

A
  • Heat in sealed tube
  • Ethanolic solvent
  • Excess of NH3
141
Q

Why must it be an ethanol solvent in the reaction of KCN and NH3 with halogenoalkanes?

A

To stop water from acting as a nucleophile

142
Q

What is the organic product of the addition of KCN to a halogenoalkane?

A

Nitriles

143
Q

What are the inorganic products of the addition of KCN to a halogenoalkane?

A

A halogen ion (e.g. Br-) or a potassium halogen (KBr)

144
Q

With the addition of KCN to a halogenoalkane, what will the organic product contain that it didn’t before the reaction?

A

One more carbon

145
Q

What does heating NH3 (ammonia) with a halogenoalkane produce?

A

Primary amines

146
Q

Why is a sealed tube needed in the addition of NH3 to a halogenoalkane?

A

Because ammonia (NH3) is a gas, so would escape the apparatus before it could react

147
Q

What is the attacking nucleophile in the addition of KCN to a halogenoalkane?

A

The CN- ion

148
Q

What is the attacking nucleophile in the addition of NH3 to a halogenoalkane?

A

The NH3 molecule

149
Q

In the addition of NH3 to a halogenoalkane, why would a salt be initially produced?

A

Because the organic product is a base, so would react with the inorganic product (the acid HI) to form a salt

150
Q

What is the equation for the first step of the conversion of 1-bromoethane to ethyl-amine?

A

CH3CH2Br + NH3 –> CH3H2NH3⁺ + Br-

151
Q

In the addition of NH3 to a halogenoalkane, what is done to turn the salt into an amine?

A

There is an excess of ammonia, which reacts with the products of the first reaction

152
Q

What is the equation of the second step of the conversion of 1-bromoethane to ethyl-amine?

A

CH3H2NH3⁺Br- + NH3 –> CH3CH2NH2 + NH4⁺Br-

153
Q

What are the two final products of the conversion of 1-bromoethane to ethyl-amine?

A

Ethyl-amine and ammonium bromide

154
Q

What type of mechanism is the addition of NH3 to a halogenoalkane to form an amine?

A

Nucleophillic substitution

155
Q

What type of mechanism is the addition of KOH to a halogenoalkane to form an alcohol?

A

Nucleophillic substitution

156
Q

Describe the mechanism for the addition of KOH to bromoethane to form an alcohol

A
  • The Br is delta negative and the C is delta negative
  • Curly arrow from C-Br bond to Br, forming Br- ion
  • Curly arrow from nucleophile OH- to now positive C, forming covalent bond
  • Final products are Ethanol and Br-
157
Q

Describe the first step of the mechanism for the addition of NH3 to bromoethane to form an amine

A
  • The Br is delta negative and the C is delta negative
  • Curly arrow from C-Br bond to Br, forming Br- ion
  • Curly arrow from nucleophile NH3 to now positive C, forming a C-N covalent bond, with 3 H attached to the N
  • The N has a +1 charge, as it has 4 covalent bonds instead of 3
158
Q

Describe the second step of the mechanism for the addition of NH3 to bromoethane to form an amine

A
  • Curly arrow from H to positive N, releasing H+ ion
  • Curly arrow from nucleophile NH3 to H+ ion, forming NH4
  • Final products are ethyl-amine and NH4 (ammonium)
159
Q

What are the possible products from the addition of NH3 to bromoethane to form an amine?

A

It is a reversible reaction, so the products will be:

  • CH3CH2NH3+ (ethylammonium bromide)
  • CH3CH2NH2 (ethyl-amine)
  • NH3 (ammonia)
  • NH4+ (ammonium)
  • Br- (bromine ion)
160
Q

What are nitriles?

A

Organic compounds containing a C-CN group

161
Q

What are primary amines?

A

Organic compounds containing the C-NH2 group

162
Q

What is a nucleophillic substitution reaction?

A

A reaction in which an attacking nucleophile (e.g. OH-) replaces an existing atom or group in a molecule

A-Level Edexcel Chemistry (24 decks)

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