The Ozone Story

Question 1

What does PPM stand for?

Answer 1

Parts per million

Amount of gas particles in a sample containing 1 million particles

Question 2

How can you calculate percentage composition from PPM?

Answer 2

ppm/1,000,000 x 100 = percentage composition

AKA ÷ by 10,000

100% = 1,000,000ppm so 1% = 10,000ppm
To convert from ppm to %, ÷ by 10,000

Question 3

How can you calculate ppm from percentage composition?

Answer 3

% compostition/100 x 1,000,000 = ppm

AKA x by 10,000

100% = 1,000,000ppm so 1% = 10,000ppm
To convert from ppm to %, ÷ by 10,000

Question 4

When might the concentration of gas in a mixture be given as percentage by volume?

Answer 4

When the gas is present in a high concentration

e.g. various gases that make up the air in the atmosphere

Question 5

When might the concentration of gas in a mixture be given in ppm?

Answer 5

If the gas is present in a low concentration - less than 1% by volume

Question 6

Why is high energy UV radiation bad for the skin?

What damage can it do?

Answer 6

Its wavelength/frequency corresponds to the energy required to break chemical bonds, such as DNA

Therefore it can damage genes and lead to skin cancer
or damage proteins and age the skin

Question 7

What is the electromagnetic spectrum?

Answer 7

The range of wavelengths/frequencies over which electromagnetic radiation extends…

Question 8

What is photodissociation?

Answer 8

Bond breaking caused by visible light/UV radiation

Question 9

What do the surfaces of the Sun and Earth both emit?

Answer 9

EM radiation

Question 10

What 2 equations link the 2 properties of light (i.e. wave-particle duality?)

Answer 10

c = λv

E = hv

Where λ = wavelength and v = frequency

Question 11

How do you calculate the frequency needed to break a bond?

AKA energy needed to cause photodissociation

Answer 11

Convert kJ/mol into J/mol by x1000

Work out the min. energy needed to break a single bond by ÷N_A

Divide energy by Planck’s constant (v = E ÷ h)

Question 12

How do you calculate bond enthalpy from frequency?

Answer 12

Calculate energy needed to break 1 bond by using E = hv

x N_A to work out energy needed to break 1mol of bonds

÷1000 to give answer in kJ/mol

Question 13

What are the 4 possible outcomes when molecules absorb EM raditation?

Put them in order of decreasing energy (highest energy to lowest)

Answer 13

Electronic transmission between energy levels

Vibration of bonds

Rotation of whole molecule

Translation of whole molecule

(Electronic transmission = requires most energy)

Question 14

Absorbtion of which types of EM radiation cause which outcomes (i.e. changes in molecule)?

Match them up

Answer 14

Electronic transmission = Visible/UV

Vibration = IR

Rotation/Translation = Microwave

Question 15

Why is the energy required to cause electronic transmission/vibration/rotation/translation given as a range despite the fact the outcomes are quantised?

Answer 15

The amount of energy needed to do each of these things changes depending on the chemical/substance

Question 16

What 3 changes to a compound/substance can electronic transmission cause?

Put them in order of decreasing energy requirement (i.e. from highest→lowest energy requirement)

Answer 16

Can cause:

Ionisation - Cl₂ → Cl₂⁺ + e^-

Dissociation - Cl₂ → Cl• + Cl•

Release of energy + return to original state

Question 17

How does the effect visible light/UV radiation have on matter differ?

Answer 17

Both cause electronic transmission…

Vissible light causes electrons to be excited to higher energy levels and some bonds break

UV causes electrons to be excited to higher energy levels and bonds break

Question 18

What are the 2 ways covalent bonds can break?

What are the products of each type of breaking?

Answer 18

Homolytic fission - produces ions

Heterolytic fission - produces radicals

Question 19

What is heterolytic fission?

Answer 19

Type of covalent bond breaking

Both electrons from a shared pair go to same species

Forms ions

Question 20

What is homolytic fission?

Answer 20

Type of covalent bond breaking

One electron from a shared pair goes to each species

Forms radicals

Question 21

What is a radical?

Answer 21

A species with one (or more) unpaired electron

Question 22

What are curly arrows used to show?

What are the 2 types and what do they denote?

Answer 22

Used to show the movement of electrons

Full (double-headed) shows movement of a pair of electrons

Half (single-headed) shows movement of a single electron

Question 23

What is a radical chain reaction?

Answer 23

A reaction in which new radicals are formed at the end of one step

These radicals then continue/propagate the reaction

Question 24

What are biradicals?

Give an example

Answer 24

Species with 2 unpaired electrons

E.g. oxygen atoms

Dots are not usually used

Question 25

What are the 3 stages of a radical chain reaction?

Briefly describe each step

Answer 25

Initiation - radicals formed from a stable molecule

Propagation - radical reacts + process forms new radical
Often occurs in pairs - radical formed in 1st propagation step reacts again in 2nd.

Termination - 2 radicals collide to form stable molecule (non-radical)

Question 26

What is the name of the mechanism/process by which a halogen atom can substitute a hydrogen atom in an alkane chain?

Answer 26

Radical substitution

N.B. alkane not alkene - halogen would undergo nucleophilic substituion instead

Question 27

Describe the stages of the radical chain reaction that occurs between alkanes and halogens

(e.g. methane + chlorine)

Answer 27

Initiation: Homolytic fission of a halogen molecule occurs in the presence of UV light
Cl₂ + hv → 2Cl•

Propagation: A methyl radical is formed, which then reacts to reform the Cl•
Hence the Cl• can be thought of as a catalyst during these steps
CH₄ + Cl• → CH₃• + HCl
CH₃• + Cl₂ → CH₃Cl + Cl•

Termination: Cl• or CH₃• radicals collide
Cl• + Cl• → Cl₂
CH₃• + Cl₃• → CH₃Cl
CH₃• + CH₃• → CH₃CH₃

The overall equation is: Cl₂ + CH₄ → CH₃Cl + HCl

Question 28

For the radical substitution reaction between chlorine and methane, why isn’t ethane included as a product in the overall equation?

Cl₂ + CH₄ → CH₃Cl + HCl

Answer 28

Because it occurs as a side reaction that isn’t as likely to happen

Due to the nature of radical reactions, an ethyl radical could be created out of it, which could collide with a methyl radical to produce a propyl radical… etc.

Hence it’s just easier to leave it out!

Question 29

What is the troposphere?

Answer 29

The layer of the atmosphere directly above Earth’s surface

Question 30

What is the stratosphere?

Answer 30

The layer of the Earth’s atmosphere above the troposphere

i.e. Above the layer directly above the Earth’s surface… 2nd layer up

Question 31

Which layer of the atmosphere is ozone naturally present in?

Answer 31

The stratosphere

Question 32

What does ozone form when it is found in the troposphere?

Answer 32

Is a component of photochemical smog

Hence is a secondary pollutant

Photochemical smog causes corrosion of plastics, rubber, textiles, and breathing problems

Question 33

What role does ozone play in the stratosphere?

Answer 33

Absorbs high-energy UV radiation from the Sun

This prevents the radiation reaching the Earth’s surface

High-energy UV can cause health problems such as skin cancer and cataracts

Question 34

Describe the steps of the depletion of ozone by chlorine atoms in the stratosphere

Answer 34

Initiation: Chloroalkanes reach the stratosphere and photodissociate, forming Cl•
CH₃Cl + hv → CH₃• + Cl•

Propagation: Cl• reacts with ozone in a catalytic cycle involving O atoms which are also present in the stratosphere
Cl• + O₃ → ClO• + O₂
ClO• + O → Cl• + O₂

Termination: Cl• removed from the cycle by the following reaction:
Cl• + Cl• → Cl₂

Question 35

Using the cancellation method, work out the overall equation for the depletion of ozone by Cl atoms in the following propagation reactions:

Cl• + O₃ → ClO• + O₂
ClO• + O → Cl• + O₂

Answer 35

Combine 2 equations with all reactants on one side and all products on the other:

Cl• + O₃ + ClO• + O → ClO• + O₂ + Cl• + O₂

Cancel out any substances that appear twice (regardless of which side) to give overall equation:

O₃ + O → 2O₂

Question 36

Using the cancellation method, work out the overall equation for the reaction of methane with chlorine in the following propagation reactions:

CH₄ + Cl• → CH₃• + HCl
CH_3• + Cl₂ → Cl• + CH₃Cl

Answer 36

Combine 2 equations with all reactants on one side and all products on the other:

CH₄ + Cl• + CH₃• + Cl₂ → CH₃• + HCl + Cl• + CH₃Cl

Cancel out any substances that appear twice (regardless of which side) to give overall equation:

CH₄ + Cl₂ → HCl + CH₃Cl

Question 37

Which haloalkanes photodissociate most easily?

Why?

What implications does this have for the atmosphere?

Answer 37

Iodo- + Bromoalkanes photodissociate more easily than chloroalkanes

This is because the C-I and C-Br bonds are weaker than C-Cl bonds

Hence they can be broken down by lower frequency radiation found in the troposphere and do not reach the stratosphere

Fluroalkanes don’t photodissociate in the stratosphere because the C-F bond is too strong to be broken by the UV radiation present

Question 38

Why can the Cl• radical present in the following porpagation steps of the depletion of ozone be described as a catalyst?

Cl• + O₃ → ClO• + O₂
ClO• + O → Cl• + O₂

Answer 38

Because it enables the second propagation stage to take place by forming an intermediate but is reformed by the end of the overall reaction

It goes through the reaction cycle many times and is not used up/depleted

Question 39

Describe how ozone is formed naturally in the stratosphere

Answer 39

Oxygen molecules photodissociate into oxygen atoms

O₂ + hv → 2O

Ozone is formed when an oxygen atom combines with an oxygen molecule

O₂ + O → O₃

Question 40

Describe how ozone is destroyed naturally in the stratosphere

Answer 40

Occurs when it absorbs high-energy UV raditation

O₃ + hv → O₂ + O

Question 41

What is reaction kinetics?

Answer 41

The study of rates of reaction

Question 42

What factors can affect rate of reaction?

Answer 42

• Concentration
• Pressure
• Use of a catalyst
• Temperature
• Surface area
• Particle size
• Intensity of radiation

Question 43

What is the general formula to measure rate of reaction?

Answer 43

Rate of reaction = change in property ÷ time taken

Question 44

What properties of a reaction could be measured to determine rate?

Answer 44

• Volume of gas evolved
• Mass change
• pH
• Colour change (colorimetry)
• Chemical analysis (i.e. taking samples, quenching, titration/colormetry)

Question 45

What is collision theory?

Answer 45

Theory that explains how the frequency of collisions between particles affects the rate of reaction

i.e. reactions only occur when particles collide with the minimum amount of kinetic energy (E_A)

More collisions = higher/faster rate

Question 46

How does increasing concentration/pressure affect the rate of reaction?

Answer 46

More particles available for collisions + in closer proximity to each other so there is a higher chance of them colliding

Therefore there is a higher chance of a successful collision occuring

(Provided the particles both have the minimum energy to react)

Question 47

How does increasing temperature increase the rate of reaction?

Answer 47

At higher temps a greater proportion of colliding particles have the sufficient energy to react so more collisions have a greater energy than the E_A

Therefore there is a higher liklihood of successful collisions occuring/more successful collisions occur

Question 48

How does increasing the surface area of a solid affect the rate of reaction?

Answer 48

When a solid is more finely divided, there is a larger surface area for reactions to take place on

This means there is a greater frequency of collisions and thus also a greater frequency of successful collisions

Rate increases

Question 49

How does the use of a heterogeneous catalyst affect the rate of reaction?

Answer 49

Provides a surface where reacting particles may break and make bonds

Increases proximity of reactants + provides an alternate pathway with lower E_A, making successful collisions/reactions more likely to take place

Question 50

How do catalysts affect the rate of reaction?

Answer 50

Provide an alternate reaction pathway with a lower E_A therefore increasing the chance of particles having the minimum amount of energy needed to successfully collide

Rate increases

Question 51

How does increasing raditation intensity affect the rate of reaction?

Answer 51

(Photo)dissociation of bonds faster when intensity increases as bonds absorb more energy per second therefore more are broken

Increases rate

Question 52

Wht general thing(s) do you need to measure in order to measure the rate of reaction

Answer 52

How quickly a reactant is used up or how quickly a product is formed

Question 53

What is activation enthalpy?

Answer 53

The minimum kinetic energy required by a pari of colliding particles in order for a successful reacton to occur

Question 54

What is a transition state?

Answer 54

The highest point on an enthalpy profile/point with highest energy on a reaction pathway

Between reactants + products forming

Where old bonds stretch and new ones start to form

Question 55

What is an enthalpy profile?

Answer 55

Graph plotting enthalpy against the progress of a reaction

Question 56

What are the main methods by which the rate of reaction can be measured experimentally?

Answer 56

• Measuring vol. gas produced - done using gas syrine or displacement of water. More gas produced per unit of time = faster rate
• Measuring mass changes - reactions which give off gas involve mass changes. Bigger change in mass per unit of time = faster rate
• Colorimetry - measures change of intensity as coloured chemical used up/produced. Measured using a colorimeter
• pH changes - if acid/alkali used up/produced, can be measured. pH meter can be used to monitor change. Faster change = faster rate

Question 57

What effect does increasing the temperature by 10ºC (roughly) have on the rate of reaction?

Answer 57

It roughly doubles

Question 58

What is the Maxwell-Boltzmann distribution?

What does it show?

Answer 58

Shows the fraction of particles with certain kinetic energy

Comparing 2 different temperatures on the distribution shows that as temp increases so does the rate of reaction

Question 59

What is needed in order for a reaction to take place?

Answer 59

Enough molecules with a combined kinetic energy that is higher than the E_a when they collide

Question 60

Why do reactions take place faster at higher temperatures?

Answer 60

Because a larger proportion of the colliding particles have the minimum E_a needed to react

Question 61

Draw a Maxwell-Boltzmann distribution showing a catalysed and un-catalysed reaction

Answer 61

Question 62

In Maxwell-Boltzmann distribution plots showing a catalysed and uncatalysed reaction OR reactions at 2 different temps, what is the same and what is different?

Answer 62

The area under the graphs is the same but the distribution is different

Question 63

How do catalysts affect the enthalpy change of a reaction?

Answer 63

They don’t

It stays the same regardless of whether a catalyst is used or not

(E_a is affected)

Question 64

What aspects of equilibrium do/don’t catalysts affect?

Answer 64

Don’t affect the position/composition of equilibirum

BUT do affect the rate at which it is reached

Question 65

What is a dipole?

Answer 65

Two opposite charges seperated by a (short) distance

Question 66

What are intermolecular bonds?

Answer 66

The bonds found in solid/liquids between molecules

Question 67

What did CFCs used to be used for/in?

Answer 67

• Refrigerants + in air can units
• Aerosol propellants
• Blowing agents for expanded plastics
• Dry cleaning solvents

Question 68

What is a polar bond?

Answer 68

A bond in which there is an uneven distribution of charge between the 2 atoms

Results in 1 atom have a partially positive (𝛿⁺) charge and 1 atom have a partially negative (𝛿^-) charge

Question 69

What is electronegativity?

Answer 69

A measure of the ability of an atom in a molecule to attract the electrons in a covalent bond

Question 70

Electronegativity is related to the position of an atom in the period table

What are the trends in electronegativity in the periodic table?

Answer 70

Electronegativity increases along a period (towards the halogens)

and going up a group

Question 71

What is the distribution of electrons like in a non-polar covalent molecule?

Answer 71

Electrons equally shared

Distance between each nucleus + electrons identical

Arrangement may also be due to equal electron affinity/electronegativity

Question 72

What is the distribution of electrons like between a larger and smaller atom?

Answer 72

Shared electrons more strongly attracted to nucleus of smaller atom as its nucleus is closer due to electron shielding in the larger atom

Question 73

What is the distribution of electrons like in atoms with different electron affinities/electronegativies?

Answer 73

The shared electrons are more stongly attracted to the nucleus with the larger charge + greater electron affinity/electronegativity

Question 74

What is another name for a permanent dipole?

Answer 74

An overall dipole

Question 75

If a molecule has symmetrical polar bonds, will it have an overall dipole?

Answer 75

No

If charges are arranged symmetrically around the central molecule then no overall dipole

However, electrons wil still be unevenly distributed in individual bonds

e. g. CCl₄
* Use bond shapes/VSEPR theory models to work it out*

Question 76

What are the 4 types of intermolecular bond?

Answer 76

Hydrogen bonds

Instantaneous dipole-induced dipole bonds

Permanent dipole-induced dipole bonds

Permanent dipole-permanent dipole bonds

Question 77

Out of all of the types of intermolecular bonds, which is the strongest?

Answer 77

Hydrogen bonds

Question 78

Which of the dipole-dipole bonds is the strongest?

Answer 78

Permanent dipole-induced dipole

Question 79

What types of dipole-dipole attractions will be present in a molecule with an overall dipole?

Answer 79

Permanent dipole-permanent dipole

AND Instantaneous dipole-induced dipole

(And possibly H-bonds)

Question 80

Describe a permanent dipole-permanent dipole bond

Answer 80

Occurs if 2 neighbouring molecules both have a permanent dipole
If so, there will be an electrostatic attraction between the charges of the dipoles

Question 81

What is an instantaneous dipole?

What causes one?

Answer 81

Arrises due to the fact electrons in constant motion

At a particular time they may not be evenly distributed

Hence a dipole may arise due to temporarily uneven charges

Question 82

What is an induced dipole?

What causes one to arise?

Answer 82

Occurs if non-polar/unpolarised molecule next to a dipole

Dipole attracts/repels electrons in unpolarised molecule, creating a dipole in it as well

Can’t occur if no permanent or instantaneous dipoles

Question 83

Describe an instantaneous dipole-induced dipole bond

Answer 83

If 2 neighbouring molecules don’t have a permanent dipole there will still be attraction between them

This is an id-id bond

Occurs between molecules even if permanent dipoles also present

Caused by constant motion of electrons. This means they may not be evenly distributed beween atoms at a given time, causing temporarily uneven charges and, therefore, a dipole

Question 84

Explain how instantaneous dipole-induced dipole bonds arise

Answer 84

Electrons in a molecule are in continuous, random motion

At a particular moment in time they may be unevenly distributed

This creates an instantaneous dipole

The dipole induces a dipole on a neighbouring molecule, creating an… induced dipole

There is an electrostatic attrction between the two dipoles

Question 85

Why do instantaneous dipole-induced dipole bonds continously break and re-form?

Answer 85

Because the electron distribution in molecules is constantly chaning due to the fact they are in continuous, random motion

Question 86

What factors affect the strength of instantaneous dipole-induced dipole bonds?

Answer 86

The no. electrons in the molecule - more means greater chance of instantaneous dipole arrising

Distance between molecules - closer packing means greater electrostatic attraction

Question 87

Why do longer chain hydrocarbons have higher boiling points than shorter chains?

Answer 87

Because longer chains increase the no. id-id bonds

Question 88

Why do branched molecules (e.g. hydrocarbons) have lower boiling points than unbranched chains?

Answer 88

Increased branching decreases the surface area of 1 molecule in contact with another hence the strength of id-id bonds is decreased

Question 89

How does the number of electrons in a molecule affect the strength of id-id bonds?

How can this be used to explain the trend in boiling points of the halogens?

Answer 89

Molecules with more electrons have more chance of forming id-id bonds

The strength of id-id bonds also increases

Hence boiling points increase as you go down the halogens (Iodine = highest)

Question 90

What is a chlorine reservoir?

Answer 90

A molecule that ‘stores’ chlorine and prevents it from reacting

e.g. HCl + ClONO₂

Question 91

When drawing a diagram to show hydrogen bonding, what should you include?

Answer 91

The lone pair(s)
The partial charges on the atoms

The correct bond angle around the H^𝛿+ atom

Dashed/dotted lines between the atoms that are hydrogen bonded

Question 92

What are the requirements for hydrogen bonding to occur?

Answer 92

A large dipole between a H atom and a highly electronegative atom (resulting in a H^𝛿​+)

A small electronegative atom in the other molecule - N, O, or F

Lone pair on NOF that H can line up/bond with

Question 93

What is the bond angle of atoms that are hydrogen bonded?

Answer 93

180º - linear (around the H^𝛿​+)

Because the lone pair (from the NOF) points directly at the H^𝛿+

Question 94

How many hydrogen bond can water form per molecule (on average)?

Why?

Answer 94

2 per molecule

Because O has 2 lone pairs and is bonded to 2 H, creating 2 H^𝛿+

Allows 2 bonds to form to neighbouring molecules

Question 95

Describe the shape and structure of ice with reference to H bonding

Answer 95

H bonds formed when water freezes gives ice a regular structure

The H bonds + covalent bonds around each O are arranged tetrahedrally

This arrangement of bonds around each O gives ice a very open structure

Hence, ice has a lower density than water and floats on it

Question 96

What properties does H bonding give molecules?

Answer 96

High viscosity - for liquid to flow molecules must be able to move past each other, so frequent/easy breaking + forming of bonds required

Solubilty in water due to fact that H bonds can form between water + molecules of substance

Question 97

What is the trend for boiling points in the halogens?

Why?

Answer 97

Boiling points increase with heavier halogen atoms + in molecules containing more halogen atoms

The larger the halogen/the more halogen atoms, the greater the overall number of electrons

This increases the number of instantaneous dipole-induced dipole bonds

This means the intermolecular bonds are stonger so more energy is needed to seperate the molecules from each other, hence they have higher boiling points

Question 98

What is the trend in bond strength in the halogens?

Why?

Answer 98

C-Hal bonds become weaker as the size of the halogen atom increases

This makes the bond easier to break and the compounds become more reactive

Although the C-F bond is the most polar, fluroalkanes are very unreactive

This shows that it is bond strength rather than bond polarity that has the greatest effect on the reactivity of halogens (it is the determining factor in reactivity)

Question 99

Describe the general reactivity of different haloalkanes

Answer 99

Fluoroalkanes - compounds are very unreactive

Chloroalkanes - compounds are reasonably stable in troposphere and can react to produce Cl radicals that deplete ozone

Bromo- and iodo-alkanes are reactive so are useful as intermediates in chemical synthesis

Question 100

What is the general equation for the homolytic fission of haloalkanes?

Answer 100

R-Hal (+ hv) → R• + Hal•

Question 101

Which haloalkane most easily undergoes homolytic fission?

Why?

Answer 101

Compounds containing the C-I bond as it has the lowest bond enthlapy

Question 102

What is the general formula for the heterolytic fission of haloalkanes?

Answer 102

R-Hal (+ hv) → R⁺ + Hal^-

Question 103

What is a carbocation?

Answer 103

An ion with a positively charged carbon atom

Question 104

What is a nucleophile?

Answer 104

A molecule or negatively charged ion with a lone pair of electrons tht it can donate to a positively charged atom to form a dative covalent bond

Means ‘nucleus loving’ and is attracted to areas of positive charge

Question 105

What are the conditions for homolytic fission (of haloalkanes?)

Answer 105

Gas phase with high temps OR the presence of UV radiation (e.g. in the stratosphere)

Question 106

What is a substitution reaction?

Answer 106

A reaction in which one atom/group in a compound is replaced by another

Question 107

What is the general equation for nucleophilic substitution reactions involving haloalkanes?

Answer 107

R-Hal + Nu^- → R-Nu + Hal^-

Question 108

Describe the stages of nucleophilic substitution

Answer 108

1. Nucelophile attacks electron deficient carbon atom in C-Hal bond
2. Nucelophile donates its lone pair to C to form a dative covalent bond
3. The carbon-halogen bond breaks heterolytically, with the halogen recieveing 2 e^- + forming a halide ion. This is the leaving group

Question 109

How many steps is there to nucleophilic substitution if the nucleophile is an ion OR a neutral molecule?

Answer 109

For an ion - 1 step

For a neutral molecule - 2 steps

Question 110

Draw the general reaction mechanism for the nucleophilic substitution of haloalkanes

Answer 110

Question 111

How can haloalkanes be synthesised?

Answer 111

By reversing nucleophilic substitution

Question 112

Draw the reaction mechanism for the nucelophilic substitution of bromobutane by hydroxide ions

Answer 112

Question 113

Draw the reaction mechanism for the nucleophilic substitution of a haloalkane by water

Answer 113

Question 114

What is a nucleophile substitution reaction involving what also called?

Answer 114

A hydrolysis reaction

Question 115

Why is water able to act as a nucleophile?

Answer 115

Because it has 2 lone pairs on the oxygen atom

Question 116

Why is ammonia able to act as a nucleophile?

Answer 116

Because it has a lone pair on the nitrogen atom

Question 117

What is the general equation for nucleophilic substitution reaction of ammonia and a haloalkane?

Answer 117

R-Hal + NH₃ → R-NH₂ + Hal^- + H⁺

Sometimes written as:

R-Hal + NH₃ → R-NH₃⁺ + Hal^- ⇌ R-NH₂ + Hal^- + H⁺

Question 118

Draw the mechanism for the reverse nucleophilic substitution of haloalkanes

(Used to synthesize them)

Answer 118

The halide ion (X^-) acts as the nucleophile

The reaction is done in the presence of a strong acid which provides a H⁺ for the O in the alcohol to bond with

This causes the oxygen to have a positive charge, so it more strongly attracts electrons from the C-O bond (bond polarised)

This causes the C to have a higher partial positive charge, causing it to be attacked by the halide ion

This causes a water molecule to become the leaving group

Question 119

When water is used as a nucleophile to react with a haloalkane, what is the/are the:

General equation

Product(s)

Reaction conditions

Answer 119

Equation:
R-Hal + H₂O → R-OH + H⁺ + Hal^-

Product:
Alcohol

Reaction Condition:
Heat under reflux - this is sometimes called hydrolysis

Question 120

When OH^- is used as a nucleophile to react with a haloalkane, what is the/are the:

General equation

Product(s)

Reaction conditions

Answer 120

General Equation:
R-Hal + OH^- → R-OH + Hal^-

Product:
Alcohol

Reaction Conditions:
Heated under reflux with NaOH_(aq) with ethanol as a solvent

Question 121

When ammonia is used as a nucleophile to react with a haloalkane, what is the/are the:

General equation

Product(s)

Reaction conditions

Answer 121

General Equation:
R-Hal + NH₃ → R-NH₂ + Hal^- + H⁺

Product:
Amine

Reaction Conditions:
Haloalkane heated with conc. ammonia solution in a sealed tube

Question 122

What are the general conditions for heterolytic fission?

Answer 122

Dissolved in a polar solvent such as an ehtanol/water mixture

Question 123

What must nucleophilic substitution reactions to make haloalkanes (from alcohols) be done in the presence of?

Answer 123

A strong acid

(To provide H⁺)