Unit 2.5 - Hydrocarbons Flashcards
Give 2 examples of types of hydrocarbons and explain why they are hydrocarbons
Alkanes and alkenes
Contain hydrogen and carbon only
What type of hydrocarbons are alkanes and alkenes?
Aliphatic hydrocarbons
Aliphatic hydrocarbons
Straight chain
What do alkanes and alkenes contain that makes them aliphatic (straight chain) hydrocarbons?
Carbon chains with C-C bonds
Which is saturated - alkanes or alkenes? Why?
Alkanes are saturated (only form single covalent bonds, C-C and C-H)
Are alkanes or alkenes unsaturated and why?
Alkenes are unsaturated
Have 1 C=C bond
What’s the main source of alkanes?
Crude oil and natural gas
What are alkanes primarily used as?
Fuels
What’s another word for crude oil?
Petroleum
What IS crude oil?
A complex mixture of saturated hydrocarbons, mainly alkanes
Describe how crude oil is formed
Formed from the remains of marine animals that lived many years ago…
Over time, they died
Sank to the bottom of the sea
Got covered in mud
The remain were compressed over time until they turned into a liquid
Collected in porous rocks like sandstone
How do we extract crude oil?
We require powerful oil rigs
What is the purpose of fractional distillation?
The first step in the separation of the different hydrocarbons in petroleum
What does fractional distillation separate substances according to?
According to their different boiling points
What’s the first step of fractional distillation?
Heated petroleum passed into a distillation column
Describe the hydrocarbons that collect at the top of the chamber during fractional distilllation
Low melting points
Short chain
More volatile (easily evaporated at normal temperatures)
Which hydrocarbons following fractional distillation are most in demand? Why?
The ones that collect at the top of the column (short chain)
Low melting point and more volatile
Place, in order, the different hydrocarbons that wold be extracted from crude oil upon fractional distillation
Gases
Gasoline
Naphtha
Kerosine
Gas oil
Residue
Example of a gas extracted from crude oil
Methane
What is gasoline?
Petrol
What is naphtha?
Chemical feedstock
Give 2 uses of kerosine
Jet fuel
Heating fuel
What is gas oil used as?
Diesel
Give 3 examples of residue from the fractional distillation of crude oil
Lubricating oil
Waxes
Bitumen
What is most of the product of the fractional distillation of crude oil?
Residue
Fractions
Mixtures of hydrocarbons of similar chain length and thus similar boiling points
Wha temperatures do fractions boil in the range of?
40 to 500 degrees Celsius
2 advantages of petrolium/crude oil
An important chemical feedstock to the chemical industry
(Many chemicals come from it and are used to prepare other organic compounds)
Relied on for the economy (used in cars and central heating systems)
2 disadvantages of crude oil/petroleum
Releases greenhouse gases
Is non-renewable
What type of bonds are the C-C and C-H bonds in alkanes?
Non-polar covalent bonds
What type of molecules are alkanes?
Non-polar
What type of forces are between alkane molecules?
Weak Van der Waal forces
Describe the melting and boiling points of alkanes
Low
What are alkanes soluble in? Why?
Non-polar solvents such as other hydrocarbons
(They’re non polar, and like dissolves with like)
What are alkanes insoluble in? Why?
Polar solvents like water
(Alkanes are non polar and like dissolves with like)
Are alkanes chemically reactive or unreactive? Why?
Unreactive
Strength of the C-C and C-H bonds
Which processes do alkanes undergo?
- Combustion
- Cracking - homolytic fission of the C-C bond
- Photo chlorination - radical attack
What is a combustion reaction?
Reaction with oxygen
Draw a diagram of the apparatus that you would use for the identification of the products of the combustion of a hydrocarbon
(See notes)
What are 2 things you’d use to identify the products of the combustion of a hydrocarbon?
Cobalt chloride paper
Limewater
What does cobalt chloride paper do?
Test for the presence of water
What would a positive test of a cobalt chloride paper show and what would this represent?
Blue to pink
Water is present
What would a positive test in limewater be and what would this represent?
Turns cloudy
CO2 is present
What colour flame do alkanes burn with?
Yellow
Do alkanes burn with a lot or a small amount of smoke?
Little or no smoke
What are most fossil fuels that are burnt to provide energy?
Alkanes
Give some examples of fossil fuels burnt to provide energy that are alkanes
Natural gas (methane)
L.P.G (propane and butane)
Petrol
Diesel
Power station oil
Marine fuel
What has the combustion of alkanes contributed to?
The greenhouse effect
Acid rain
Photochemical smog
How has the combustion of alkane contributed to acid rain?
Combusting impurities in the fuels
Why are alternative fuels being sought from alkanes?
They contribute to things like the greenhouse effect, acid rain and photochemical smog
When would an alkane undergo incomplete combustion?
In a lack of oxygen
What does the incomplete combustion of an alkane produce?
Carbon monoxide (CO)
What’s the problem with carbon monoxide?
Highly toxic
Why is carbon monoxide toxic?
Binds to haemoglobin, effecting gas exchange
Why is it important to keep stoves in good condition?
So that they have enough oxygen so that incomplete combustion doesn’t occur and form carbon monoxide
Products of incomplete combustion
Carbon monoxide (CO)
Water (often present as steam - use state symbol ‘g’)
In what form is the water produced from combustion?
Often as steam
(Use state symbol ‘g’)
What is cracking?
The process where large, less useful hydrocarbon molecules are broken down into smaller, more useful molecules
What will the useful molecules of cracking be?
A mixture of saturated and unsaturated hydrocarbons
Why are smaller molecules from cracking more useful than larger ones?
They burn easier
Why do smaller molecules burn easier? What does this make them?
Lower boiling temperature = evaporate better, and it’s the vapour of a fuel that burns
= better fuels
What is an alternative thing that can occur during cracking?
Straight chain alkanes are converted into branched alkanes
What is one of the main fractions cracked?
Naphtha
What conditions are required for cracking?
Very high temperatures and pressure
How is naphtha cracked?
Feedstock is heated to around 800 degrees Celsius (very high temperature and pressure)
Steam is added to dilute the feedstock
What are some fractions obtained from naphtha?
Methane
Ethene
Propene
Petrol
Other alkenes
What does cracking always form?
A smaller chain hydrocarbon and an alkene
What does cracking involve the formation of?
Free radicals
Why does cracking involve the formation of free radicals?
The C-C bond is broken at the high temperatures used
What has happened to the C-C bond in a hydrocarbon when it’s been broken at the high temperatures of cracking?
The homolysis of the C-C bod
When does the homolysis of the C-C bond in a hydrocarbon occur?
When the C-C bond is broken at the high temperatures used
What are the 2 ways that covalent bonds in organic compounds can break?
Homolytic bond fission
Heterolytic bond fission
What are homolytic and heterolytic bond fission examples of?
Ways that the covalent bonds in organic compounds can break
Homolytic bond fission
The covalent bonds break in such a way that each atom forming the bond retains one electron
What is the species formed from homolytic bond fission and why?
A free radical (has an unpaired electron)
Describe free radicals
Very reactive
Describe and give examples of reactions involving free radicals
Very rapid
E.g - photo chlorination of methane and cracking
Heterolytic bond fission
The covalent bonds break in such a way that one atom takes both electrons in the bond
What’s the most common type of bond fission?
Heterolytic bond fission
How are reactions involving heterolytic bond fission different to those involving homolytic bond fission?
Much slower
What does heterolytic bond fission form?
An electrophile and a nucleophile
Fission
The breaking of a chemical bond
What type of property is boiling point?
Physical
What physical property of molecules is used to separate them during fractional distillation?
Boiling points
What does methane react with and how?
Chlorine, vigorously
Under which conditions does methane react vigorously with chlorine
In sunlight (UV light)
Under which conditions would methane not react with chlorine? Why?
In the dark
The photo chlorination of methane required UV light
What’s the name for methane reacting with chlorine?
Photo chlorination of methane
What type of reaction is the photo chlorination of methane?
Free radical substitution
Write the reaction to form chloromethane
CH4 + Cl2 —> CH3Cl + HCl
Write the reaction to form dichloromethane
CH3Cl + Cl2 —> CH2Cl2 + HCl
What can also be formed in the photo chlorination of methane as well as chloromethane and dichloromethane and how?
Trichloroethane and tetrachloromethane
The products of the reaction before can react with further chlorine molecules
Why is the photo chlorination of methane a free radical substitution reaction?
Hydrogen atoms in the alkanes are substituted for chlorine atoms
What are the three steps to a free radical substitution reaction?
Initiation
Propagation
Termination
What happens during the initiation stage for free radical substation during the photo chlorination of methane?
Chlorine molecules in UV light undergo homolytic fissio
Forms free radicals
How much energy is required for the formation of free radicals during the initiation stage of free radical substation for the photo chlorination of methane?
A considerable amount - equivalent to the bond enthalpy of chlorine molecules
What type of reaction is initiation during free radical substitution?
Endothermic
Write the equation for the initiation stage of the free radical substitution reaction during the photo chlorination of methane
Cl2 —> 2Cl•
What happens during the propagation stage for free radical substation during the photo chlorination of methane?
Involves the formation of products
Chlorine radicals reform in the course of the reaction and are able to react with more methane molecules
Describe the propagation stage (2 separate things) of free radical substitution. Why is this?
Very fast due to the presence of free radicals
Self-sustaining due to chlorine radicals reforming in the course of the reaction that are able to react with more methane molecules
Why is the propagation stage of the photo chlorination of methane self-sustaining?
Chlorine radicals reform in the course of the reaction and so are able to react with more methane molecules
What type of reaction is the propagation stage of free radical substitution?
Chain reaction
What does the fact that the propagation stage of free radical substitution is a chain reaction mean for it?
One chlorine radical can react with many thousand methane molecules in a fraction of a second
Write the equations for the formation of chloromethane
CH4 + Cl• —> CH3 • + HCl
CH3 • + Cl —> CH2Cl2 + Cl •
Write the equations for the formation of dichloromethane
CH3Cl + Cl • —> CH2Cl • + HCl
CH2Cl • + Cl2 —> CH2Cl2 + Cl •
What happens during the termination stage for free radical substation during the photo chlorination of methane?
All remaining free radicals combine and are destructed
Where do the remaining free radicals usually combine at the termination stage of free radical substitution?
On the walls of the reaction vessel
What does the termination stage of free radical substitution produce?
Stable products that are organic molecules
Show free radicals combining to form ethane
CH3 • + CH3 • —> CH3CH3