Organic - Alkanes Flashcards
What are alkanes?
Alkanes are a homologous series of saturated hydrocarbons with the general formula CnH2n+2.
Are alkanes reactive?
Alkanes are very unreactive because they’re non-polar, although they do burn and react with halogens. Harsh conditions are required to break them down.
How does the carbon chain affect the boiling point of alkanes?
The longer the carbon chain, the higher the boiling point due to stronger van der Waals’ forces between molecules (because there are more electrons in the molecules).
How do the isomers of an alkane affect the boiling point?
For alkanes that are isomers, the more branched the carbon chain, the lower the boiling point due to weaker van der Waals’ forces between molecules (due to molecules not being able to pack as close together).
How are deposits of crude oil and natural gas formed?
Deposits of crude oil and natural gas usually occur together and they are formed by the slow decay of marine animals and plants, over millions of years, under heat and pressure in the absence of air.
What is crude oil composed of?
Although the exact composition of crude oils vary around the world, all are a complex mixture consisting mainly of alkanes (including cycloalkanes, some aromatics and other compounds containing some sulphur and oxygen).
How is crude oil used?
Crude oil has no use in its raw form, so to provide useful products its components must be partly separated (and if necessary modified) - the separation uses the differences in the physical properties of alkanes.
How is crude oil separated?
The compounds in crude oil have different boiling points and this is used to separate them by fractional distillation at an oil refinery.
C-H bonds are virtually non-polar, so there are only van der Waals’ forces between molecules. As the alkane chain gets longer, the melting and boiling points increase due to greater van der Waals’ forces.
What is the basic idea of the separation process?
- The crude oil is first heated in a furnace.
- A mixture of liquid and vapour is passed into a tower which is hot at the bottom and cold at the top.
- The vapours pass up the tower via a series of trays containing bubble caps until they arrive at a tray that is sufficiently cool (at a lower temperature than their boiling point). Then they condense to liquid.
- Molecules will condense at different heights as they have different boiling points.
- The mixture of liquids that condenses on each tray is piped off.
- The larger the molecule (with higher boiling points), the lower down the column it condenses.
- This produces a fraction.
- The thick residue that collects at the base of the tower is called tar or bitumen. It can be used for road surfaces and roofing but, as supply often exceeds demand, this fraction is often further processes to give more valuable products.
What is a fraction?
A fraction is a mixture of compounds (hydrocarbons) with similar boiling points.
What happens to the hydrocarbons as the carbon chain gets longer?
As the carbon chain gets longer, the hydrocarbons:
- become more viscous
- become harder to ignite
- become less volatile
- have higher boiling points
Give the order of the fractions from the lowest boiling point to the highest. What are their uses?
- fuel gases (Calor gas, LPG)
- gasoline (petrol for cars)
- naphtha (petrochemicals)
- kerosene (jet fuel)
- diesel/gas oil (fuel for diesel engines)
- residue: distilled further at lower pressures to give fuel oil, lubricating oil, waxes, and bitumen
Why is the residue from the primary distillation separated further?
The residue from the primary distillation (first distillation) contains useful substances, such as fuel oil, lubricating oil, waxes and bitumen, that boil above 350 degrees Celsius at atmospheric pressure. However, they would decompose at such high temperatures, so they are separated further by distillation at a lower pressure (vacuum distillation).
Which fractions are most in-demand?
The petroleum fractions (lower boiling points) with shorter carbon chains (e.g. petrol and naphtha) are in more demand than larger fractions. However, they are the least abundant.
How do you supply demand for shorter carbon chains?
To make use of excess larger hydrocarbons and supply demand for shorter ones, longer hydrocarbons are cracked.
What is cracking?
Cracking is the thermal decomposition of alkanes. Carbon-carbon bonds are broken in cracking. The products of cracking are more valuable than the starting materials (e.g. ethene used to make poly(ethene), branched alkanes for motor fuels, etc.)
What are the conditions for thermal cracking?
temperature - 900 degrees Celcius pressure - 70 atm mechanism - homolytic fission catalyst - none products - alkenes uses of products - making polymers
What are the conditions for catalytic cracking?
temperature - 450 degrees Celcius pressure - 1-2 atm (slight pressure) mechanism - heterolytic fission catalyst - zeolites products - motor fuels, aromatic hydrocarbons, cycloalkanes, branched alkanes) uses of products - fuel
What is reforming?
Reforming is a process where straight chain hydrocarbons are converted into branched chain alkanes and cyclic alkanes. Both these products burn more efficiently and are used in petrol for cars.
How do alkanes undergo combustion?
Alkanes readily burn in the presence of oxygen and release vast amounts of energy, this combustion of alkanes being highly exothermic, explaining their use as fuels.
What are the products of complete combustion?
Alkanes burn in a plentiful supply of oxygen to produce carbon dioxide and water only.
What are the products of incomplete combustion?
In a limited supply of air, alkanes will burn to form water and carbon monoxide. If the supply of oxygen is further limited, solid carbon particles (soot) are formed.
Why isn’t hydrogen produced during combustion?
Any amount of oxygen present binds to hydrogen first to produce water.
What is the polarity of alkanes?
Alkanes are almost no-polar because the electronegativities of carbon and hydrogen are so similar. As a result, the only intermolecular forces between their molecules are weak van der Waals forces, and the larger the molecule, the stronger the van der Waals forces.
What are the boiling points of alkanes?
The increasing intermolecular force is why the boiling points of alkanes increase as the chain length increases. The shorter chains are gases at room temperature. Pentane, with five carbons, is a liquid with a low boiling point of 309K. At a chain length of about 18 carbons, the alkanes become solids at room temperature. The solids have a waxy feel.
Alkanes with branched chains have lower melting points than straight chain alkanes with the same number of carbon atoms. This is because they cannot pack together closely as unbranched chains and so the van der Waals forces are not so effective.
What is the solubility of alkanes?
Alkanes are insoluble in water. This is because water molecules are held together by hydrogen bonds which are much stronger than the van der Waal’s forces that act between alkane molecules. However, alkanes do mix with other relatively non-polar liquids.
How do alkanes react?
Alkanes are relatively unreactive. They have strong carbon-carbon and carbon-hydrogen bonds. They do not react with acids, bases, oxidising agents, and reducing agents. However, they do burn and they will react with halogens under suitable conditions. They burn in a plentiful supply of oxygen to form carbon dioxide and water (or, in a restricted supply of oxygen, to form carbon monoxide or carbon).
How is sulphur dioxide produced?
Crude oil contains small amounts of other compounds dissolved in it. These come from other elements in the original plants and animals the oil was formed from, for example, some contain sulphur. These produce sulphur dioxide when they are burnt. This is one of the causes of acid rain - sulphur dioxide reacts with oxygen high in the atmosphere to form sulphur trioxide. This reacts with water in the atmosphere to form sulphuric acid.
What is broken during fractional distillation?
Fractional distillation is a physical process so no covalent bonds within the molecules are broken. It is the van der Waals forces between the molecules that are broken during vaporisation and reform on condensing.
What is fracking?
Many areas of the UK have resources of natural gas trapped within shale rock. This gas can be extracted by drilling into the shale and forcing pressurised water mixed with sand into the shale. This causes the rather soft shale rock to break up or fracture (giving the term fracking, short for hydraulic fracturing) releasing the trapped gas which flows to the surface. A number of chemicals are added to the water such as hydrochloric acid to help break up the shale and methanol to prevent corrosion in the system.
Why are people opposed to fracking?
- They do not like the infrastructure of wells and the associated traffic in their ‘background’.
- There is concern about the amount of water used.
- They worry about the chemical additives polluting water supplies.
- Occasionally fracking appears to have caused small earthquakes.
- Burning natural gas produces carbon dioxide (a cause of global warming).
Set against these objectives is the appeal of gas supplies for many years which are not subject to control by other countries.
What are seven different pollutants?
- CO2
- CO
- C (soot)
- H2O
- SO2
- NOx
- unburned hydrocarbons
What is CO2? (how is it formed? what are the problems it causes? what are the ways to reduce the problem?)
How formed - complete combustion of fuels containing C
Problem caused - greenhouse gas
Ways to reduce the problem - burn less fossil fuels
What is CO? (how is it formed? what are the problems it causes? what are the ways to reduce the problem?)
How formed - incomplete combustion of fuels containing C
Problem caused - toxic
Ways to reduce the problem - ensure a good supply of oxygen when burning fuels
What is C (soot)? (how is it formed? what are the problems it causes? what are the ways to reduce the problem?)
How formed - incomplete combustion of fuels containing C
Problem caused - blackens buildings, can cause respiratory problems, global dimming
Ways to reduce the problem - ensure a good supply of oxygen when burning fuels
What is H2O? (how is it formed? what are the problems it causes? what are the ways to reduce the problem?)
How formed - combustion of fuels containing H
Problem caused - greenhouse gas
Ways to reduce the problem -
What is SO2? (how is it formed? what are the problems it causes? what are the ways to reduce the problem?)
How formed - combustion of S containing compounds in fuel
Problem caused - acid rain
Ways to reduce the problem - remove S from fuel before burning, flue gas desulfurisation