Triple

Triple-Science-only spec point

3:06 (Triple only) know that bond-breaking is an endothermic process and that bond-making is an exothermic process

During chemical reactions, the bonds in the reactants must be broken, and new ones formed to make the products.

Breaking bonds need energy and therefore is described as endothermic.

Energy is released when new bonds are made and therefore is described as exothermic.

 

If bonds are both broken and made during chemical reactions, why can a reaction overall be describe as either exothermic or endothermic?

Example: hydrogen reacts with oxygen producing water. Overall energy is released and therefore the reaction is exothermic.

         

The reaction is exothermic because the energy needed to break the bonds is less than the energy released in making new bonds.

If a reaction is endothermic then the energy needed to break the bonds is more than the energy released in making new bonds.

3:07 (Triple only) use bond energies to calculate the enthalpy change during a chemical reaction

Each type of chemical bond has a particular bond energy. The bond energy can vary slightly depending what compound the bond is in, therefore average bond energies are used to calculate the change in heat (enthalpy change, ΔH) of a reaction.

Example: dehydration of ethanol

Note: bond energy tables will always be given in the exam, e.g:

BondAverage bond energy in kJ/mol
H-C412
C-C348
O-H463
C-O360
C=C612

So the enthalpy change in this example can be calculated as follows:

Breaking bondsMaking bonds
BondsEnergy (kJ/mol)BondsEnergy (kJ/mol)
H-C x 5(412 x 5) = 2060C-H x 4(412 x 4) = 1648
C-C348C=C612
C-O360O-H x 2(463 x 2) = 926
O-H463
Energy needed to break all the bonds3231Energy released to make all the new bonds3186

Enthalpy change, ΔH = Energy needed to break all the bonds - Energy released to make all the new bonds

ΔH = 3231 – 3186 = +45 kJ/mol (ΔH is positive so the reaction is endothermic)

3:14 (Triple only) draw and explain reaction profile diagrams showing ΔH and activation energy

Below is a diagram showing the reaction profile for the reaction of hydrogen with oxygen, which is EXOTHERMIC:

The activation energy is the minimum amount of energy required to start the reaction.

For an exothermic reaction, the products have less energy than the reactants. The difference between these energy levels is ΔH.

For an exothermic reaction, more energy is released when bonds are formed than taken in when bonds are broken.

 

Below is a diagram showing the reaction profile for the thermal decomposition of calcium carbonate, which is ENDOTHERMIC:

The activation energy is the minimum amount of energy required to start the reaction.

For an endothermic reaction, the products have more energy than the reactants. The difference between these energy levels is ΔH.

For an endothermic reaction, more energy is taken in to break bonds than is released when new bonds are formed.

3:20 (Triple only) know that the characteristics of a reaction at dynamic equilibrium are: the forward and reverse reactions occur at the same rate, and the concentrations of reactants and products remain constant

Features of a reaction mixture that is in dynamic equilibrium:

  1.   the concentrations of reactants and products remain constant
  2.   rate of forward reaction = rate of backward reaction

3:21 (Triple only) understand why a catalyst does not affect the position of equilibrium in a reversible reaction

A catalyst is a substance which increases the rate of reaction without being chemically changed at the end of the reaction.

A reversible reaction is one where the forward reaction and the backward reaction happen simultaneously. For example:

3H₂ + N₂ ⇋ 2NH₃

In such a reaction a catalyst speeds up both the forward and the backward reactions. Hence, although the system will reach dynamic equilibrium more quickly, the addition of a catalyst will not affect the position of equilibrium.

3:22 (Triple only) predict, with reasons, the effect of changing either pressure or temperature on the position of equilibrium in a reversible reaction (references to Le Chatelier’s principle are not required)

In a reversible reaction the position of the equilibrium (the relative amounts of reactants and products) is dependent on the temperature and pressure of the reactants.

If the conditions of an equilibrium reaction are changed, the reaction moves to counteract that change.

Therefore by altering the temperature or pressure the position of the equilibrium will change to give more or less products.

Adding a catalyst does not affect the position of the equilibrium.

 

If a change in conditions moves equilibrium to the right, the yield of the substances on the right is increased.

 

Changing the temperature:

All reactions are exothermic in one direction and endothermic in the other way.

For this reaction the enthalpy change, ΔH is negative therefore the forward reaction is exothermic:

     CO(g)     +             2H2(g)                    ⇌            CH3OH(g)              ΔH = –91 kJ/mol

If temperature is decreased the position of the equilibrium will shift to the right because it is an exothermic reaction.

For this reaction the enthalpy change, ΔH is positive therefore the forward reaction is endothermic:

     CH4(g)                     +              H2O(g)                    ⇌            CO(g)      +              3H2(g)                     ΔH = +210 kJ mol–1

If temperature is increased the position of the equilibrium will shift to the right because it is an endothermic reaction.

Key point: an increase (or decrease) in temperature shifts the position of equilibrium in the direction of the endothermic (or exothermic) reaction

 

Changing the pressure:

Reactions may have more molecules of gas on one side than on the other.

For this reaction there are 2 molecules on the left and 4 molecules on the right:

     CH4(g)                     +              H2O(g)                    ⇌            CO(g)      +              3H2(g)                     ΔH = +210 kJ mol–1

If the pressure is increased the position of the equilibrium will shift to the left because there are fewer molecules on the left-hand side.

For this reaction there are 3 molecules on the left and 1 molecule on the right

     CO(g)     +             2H2(g)                    ⇌            CH3OH(g)              ΔH = –91 kJ/mol

If the pressure is decreased the position of the equilibrium will shift to the left because there are more molecules on the left-hand side.

Key point: an increase (or decrease) in pressure shifts the position of equilibrium in the direction that produces fewer (or more) moles of gas

4:29 (Triple only) know that alcohols contain the functional group −OH

The member of the homologous series called Alcohols have names which end in “ol”. Examples are methanol, ethanol and propanol.

Alcohols all contain an -OH functional group attached to a hydrocarbon chain.

4:30 (Triple only) understand how to draw structural and displayed formulae for methanol, ethanol, propanol (propan-1-ol only) and butanol (butan-1-ol only), and name each compound, the names propanol and butanol are acceptable

Structural formula and displayed formula for methanol:

CH₃-OH

 

Structural formula and displayed formula for ethanol:

CH₃-CH₂-OH                    (or simply C₂H₅OH)

Image result for ethanol

 

Structural formula and displayed formula for propan-1-ol:

CH₃-CH₂-CH₂-OH

 

Structural formula and displayed formula for butan-1-ol:

CH₃-CH₂-CH₂-CH₂-OH

 

4:31 (Triple only) know that ethanol can be oxidised by: burning in air or oxygen (complete combustion), reaction with oxygen in the air to form ethanoic acid (microbial oxidation), heating with potassium dichromate(VI) in dilute sulfuric acid to form ethanoic acid

1) Ethanol can be oxidised by complete combustion. With excess oxygen the complete combustion of ethanol (C₂H₅OH) in air produces carbon dioxide and water:

C₂H₅OH (l)         +         3O₂ (g)         →         2CO₂ (g)         +         3H₂O (l)

 

2) Ethanol can be oxidised in air in the presence of microorganisms (‘microbial oxidation’) to form ethanoic acid (CH₃COOH).

 

3) Ethanol can be oxidised by heating with the oxidising agent potassium dichromate(VI) (K₂Cr₂O₇) in dilute sulfuric acid (H₂SO₄).

In the equation below, [O] means oxygen from an oxidising agent.

CH₃CH₂OH         +         2[O]         →         CH₃COOH         +         H₂O

This mixture starts orange but when the reaction happens turns green which indicates the presence of Cr³⁺ ions which are formed when the potassium dichromate(VI) is reduced.

4:32 (Triple only) know that ethanol can be manufactured by: 1) reacting ethene with steam in the presence of a phosphoric acid catalyst at a temperature of about 300⁰C and a pressure of about 60–70atm; and 2) the fermentation of glucose, in the absence of air, at an optimum temperature of about 30⁰C and using the enzymes in yeast

In the hydration of ethene, ethanol is made by passing ethene and steam over a catalyst.

Water is added to ethene, this is known as hydration.

Conditions

Catalyst: Phosphoric acid (H3PO4)

Temperature: 300°C

Pressure: 60 atm

 

 

Fermentation is the conversion of sugar, e.g. glucose into ethanol by enzymes from yeast.

 

Conditions

Catalyst: Zymase (enzyme found in yeast)

Temperature: 30°C  –  The process is carried out at low temperatures as not to denature the enzymes.

Other: Anaerobic (no oxygen present) – if oxygen were present, the yeast produce carbon dioxide and water instead of ethanol.

 

4:33 (Triple only) understand the reasons for fermentation, in the absence of air, and at an optimum temperature

In the production of ethanol the process of fermentation is carried out at a low temperature (30⁰-40⁰).

Above 40⁰ the enzymes would permanently lose their structure (denature).

At a temperature lower than 30⁰ the process would be too slow.

 

Fermentation is conducted in the absence of air. In the presence of air (aerobic conditions), enzymes in the yeast produce carbon dioxide and water instead of ethanol.

Also, in the presence of air, the ethanol can oxidise to ethanoic acid.

 

4:35 (Triple only) understand how to draw structural and displayed formulae for unbranched- chain carboxylic acids with up to four carbon atoms in the molecule, and name each compound

The four simplest carboxylic acids are methanoic acid, ethanoic acid, propanoic acid and butanoic acid.

 

Methanoic acid

Displayed formula:Image result for methanoic acid

Molecular formula: CH₂O₂

Structural formula: HCOOH

 

Ethanoic acid

Displayed formula:

Molecular formula: C₂H₄O₂

Structural formula: CH₃COOH

 

Propanoic acid

Displayed formula:Image result for propanoic acid

Molecular formula: C₃H₆O₂

Structural formula: CH₃CH₂COOH

 

Butanoic acid

Displayed formula:Image result for butanoic acid

Molecular formula: C₄H₈O₂

Structural formula: CH₃CH₂CH₂COOH

4:36 (Triple only) describe the reactions of aqueous solutions of carboxylic acids with metals and metal carbonates

Dilute carboxylic acids react with metals in the same way as other dilute acids (e.g. hydrochloric acid) only more slowly.

For example, dilute ethanoic acid reacts with magnesium with a lot of fizzing to produce a salt and hydrogen, leaving a colourless solution of magnesium ethanoate:

magnesium      +      ethanoic acid      →      magnesium ethanoate      +      hydrogen

Mg (s)         +         2CH₃COOH (aq)         →         (CH₃COO)₂Mg (aq)         +         H₂ (g)

 

Dilute carboxylic acids react with metal carbonates as they do with other acids, to give a salt, carbon dioxide and water.

For example, dilute ethanoic acid reacts with sodium carbonate with a lot of fizzing to produce a salt,  carbon dioxide and water, leaving a colourless solution of sodium ethanoate:

sodium carbonate      +      ethanoic acid      →      sodium ethanoate      +      carbon dioxide      +      water

Na₂CO₃ (s)         +         2CH₃COOH (aq)         →         2CH₃COONa (aq)         +         CO₂ (g)         +         H₂O (l)

 

As can be seen in the examples above the charge on the ethanoate ion is -1.

 

4:39 (Triple only) know that ethyl ethanoate is the ester produced when ethanol and ethanoic acid react in the presence of an acid catalyst

Ethyl ethanoate is the ester produced when ethanol and ethanoic acid react in the presence of an acid catalyst.

ethanoic acid           +           ethanol           ⇋           ethyl ethanoate           +           water

CH₃COOH (l)         +         CH₃CH₂OH (l)         ⇋         CH₃COOCH₂CH₃ (l)         +         H₂O (l)

The ethyl ethanoate produced is an ester.

The reaction is called esterification.

The reaction can also be described as a condensation reaction because water is made when two molecules join together.

4:41 (Triple only) understand how to write the structural and displayed formulae of an ester, given the name or formula of the alcohol and carboxylic acid from which it is formed and vice versa

To work out the structure of the ester formed when an alcohol reacts with a carboxylic acid, it is easiest to first draw the structures of alcohol and acid and then remove the H₂O to see what is left when the molecules join.

For example, propan-1-ol and ethanoic acid react together to form propyl ethanoate and water.

         propan-1-ol            +            ethanoic acid            →            propyl ethanoate            +            water

         CH₃CH₂CH₂OH (l)         +         CH₃COOH (l)         →         CH₃COOCH₂CH₂CH₃ (l)          +         H₂O (l)

 

The displayed formula for esters is typically written to show the part which came from the carboxylic acid on the left:

This is still called propyl ethanoate: the alcohol bit of the name (propyl) comes first and then the carboxylic acid bit (ethanoate), even though the displayed formula is typically written the other way around. Notice that the structural formulae for esters is also typically written with the carboxylic acid bit first, so propyl ethanoate is CH₃COOCH₂CH₂CH₃.

4:42 (Triple only) know that esters are volatile compounds with distinctive smells and are used as food flavourings and in perfumes

Esters are volatile compounds with distinctive smells. A volatile liquid is one that turns into to a vapour easily.

Esters are used as food flavourings and in perfumes.

Esters are often described as having a sweet, fruity smell. They typically smell of bananas, raspberries, pears or other fruit because esters occur in all these natural products.

4:43 (Triple only) practical: prepare a sample of an ester such as ethyl ethanoate

Heating a mixture of ethanoic acid and ethanol produces a liquid called ethyl ethanoate. A few drops of concentrated sulfuric acid must be added for the reaction to work. The sulfuric acid acts as a catalyst.

ethanoic acid           +           ethanol           ⇋           ethyl ethanoate           +           water

CH₃COOH (l)         +         CH₃CH₂OH (l)         ⇋         CH₃COOCH₂CH₃ (l)         +         H₂O (l)

The ethyl ethanoate produced is an ester.

The reaction is called esterification.

The reaction can also be described as a condensation reaction because water is made when two molecules join together.

Notice that the reaction is reversible. Pure reactants are used to maximise the yield of ethyl ethanoate. Pure ethanoic acid is called glacial ethanoic acid.

4:48 (Triple only) know that condensation polymerisation, in which a dicarboxylic acid reacts with a diol, produces a polyester and water

Condensation polymers are formed by a condensation reaction.

These polymers are formed by the combination of two different monomers, such as a dicarboxylic acid and a diol.

When these particular monomers join in an alternating pattern they form a long polymer called a polyester. Where each monomer joins to the next, a separate molecule of water is also produced.

 

 

4:49 (Triple only) Understand how to write the structural and displayed formula of a polyester, showing the repeat unit, given the formulae of the monomers from which it is formed, including the reaction of ethanedioic acid and ethanediol:

Polyesters are polymers formed when two types of monomer join together alternately. Where each joins to the next a small molecule, such as water or hydrogen chloride, is lost. This is called a condensation polymerisation reaction.

 

One of the monomers is a diol, an alcohol with a -OH functional group at each end. An example is hexane-1,6-diol which has the structural formula CH₂OHCH₂CH₂CH₂CH₂CH₂OH and the displayed formula:

Since it is only the -OH functional groups which are important for polymerisation, this can we re-written with the central block of carbons represented as a block:

 

The other monomer is a dicarboxylic acid, a molecule with a -COOH functional group at each end. An example is hexane-1,6-dioic acid which has the structural formula HOOCCH₂CH₂CH₂CH₂COOH and the displayed formula:

Since it is only the -COOH functional groups which are important for polymerisation, this can we re-written with the central block of 4 carbons represented as a block:

 

These two different types of monomer (the diol and the dicarboxylic acid) can join to form a polymer with the loss of a water molecule at every bond. As above, this can be simplified by only looking at the functional groups and representing the other carbons as blocks, so the whole process looks like:

 

A simple example of this is the condensation polymerisation reaction between ethanedioic acid and ethandiol:

4:50 (Triple only) know that some polyesters, known as biopolyesters, are biodegradable

There are environmental issues with the disposal of condensation polymers, though because of their ester linkage the issues are not as severe as with addition polymers. Normally condensation polymers can take hundreds of years to break down, but chemists has developed biopolyesters which break down much more quickly.

Select a set of flashcards to study:

     Terminology

     Skills and equipment

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Section 1: Principles of chemistry

      a) States of matter

      b) Atoms

      c) Atomic structure

     d) Relative formula masses and molar volumes of gases

     e) Chemical formulae and chemical equations

     f) Ionic compounds

     g) Covalent substances

     h) Metallic crystals

     i) Electrolysis

 Section 2: Chemistry of the elements

     a) The Periodic Table

     b) Group 1 elements: lithium, sodium and potassium

     c) Group 7 elements: chlorine, bromine and iodine

     d) Oxygen and oxides

     e) Hydrogen and water

     f) Reactivity series

     g) Tests for ions and gases

Section 3: Organic chemistry

     a) Introduction

     b) Alkanes

     c) Alkenes

     d) Ethanol

Section 4: Physical chemistry

     a) Acids, alkalis and salts

     b) Energetics

     c) Rates of reaction

     d) Equilibria

Section 5: Chemistry in industry

     a) Extraction and uses of metals

     b) Crude oil

     c) Synthetic polymers

     d) The industrial manufacture of chemicals

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