Alkanes: Saturated Hydrocarbons

me when tetravalence

The two kinds of water

Credit: University of Basel

Pre-sorted ortho-water and para-water molecules with differently oriented nuclear spins (blue or red arrows) react with diazenylium ions (centre left) at different speeds.

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Researchers from the University of Basel’s Department of Chemistry, Switzerland, has investigated how the two forms of water differ in terms of their chemical reactivity – the ability to undergo a chemical reaction. Both forms have almost identical physical properties, which makes their separation particularly challenging.

It is less well-known that water exists in two different forms (isomers) at the molecular level. The difference is in the relative orientation of the nuclear spins of the two hydrogen atoms. Depending on whether the spins are aligned in the same or opposite direction, one refers to ortho- or para-water.

The was made possible by a method based on electric fields. Using this, researchers were able to initiate controlled reactions between the pre-sorted water isomers and ultracold diazenylium ions (protonated nitrogen) held in a trap. During this process, a diazenylium ion transfers its proton to a water molecule. This reaction is also observed in the chemistry of interstellar space.

It was discovered that para-water reacts about 25% faster than ortho-water. This can be explained in terms of the nuclear spin also influencing the rotation of the water molecules. As a result, different attractive forces act between the reaction partners. Para-water is able to attract its reaction partner more strongly than the ortho-form, which leads to an increased chemical reactivity. 

It’s World Sleep Day

Log off.

Go back to bed.

i just learned from animal crossing that pondskaters stay on top of the water by secreting an oil from their feet

that seems kinda obvious in hindsight. i always figured they were just, like, light enough to not break surface tension

#OTD a year ago, Moderna’s RNA vaccine became the first #COVID19 vaccine to enter phase 1 trials. The latest #ChemVsCOVID graphic with the Royal Society of Chemistry takes a brief look at how prior research helped COVID vaccines reach this point quickly: https://ift.tt/3cE5xHR https://ift.tt/3rV4v0F

Halogenoalkanes

Halogenoalkanes are a homologous series of saturated carbon compounds that contain one or more halogen atoms. They are used as refrigerants, solvents, flame retardants, anaesthetics and pharmaceuticals but their use has been restricted in recent years due to their link to pollution and the destruction of the ozone layer.  

They contain the functional group C-X where X represents a halogen atom, F,Cl, Br or I. The general formula of the series is CnH2n+1X.

The C-X bond is polar because the halogen atom is more electronegative than the C atom. The electronegativity decreases as you go down group 7 therefore the bond becomes less polar. Flourine has a 4.0 EN whereas iodine has a 2.5 EN meaning it is almost non-polar.

The two types of intermolecular forces between halogenoalkane molecules are Van Der Waals and permanent dipole-dipole interactions. As the carbon chain length increases, the intermolecular forces (due to VDWs) increase as the relative atomic mass increases due to more electrons creating induced dipoles. Therefore the boiling point of the halogenoalkanes increases since more forces must be broken.  

Branched chains have lower boiling points than chains of the same length and halogen because the VDWs are working across a greater distance and are therefore weaker.

When the carbon chain length is kept the same, but the halogen atom is changed, despite the effect of the changing polar bond on the permanent dipole-dipole interactions, the changing VDWs have a greater effect on the boiling point. Therefore as RAM increases, the boiling point increases meaning an iodoalkane has a greater boiling point than a bromoalkane if they have the same carbon chain length.  

Halogenoalkanes are insoluble or only slightly soluable in water despite their polar nature. They are soluble in organic solvents such as ethanol and can be used as dry cleaning agents because they can mix with other hydrocarbons.

Summary

Halogenoalkanes are saturated carbon compounds with one or more halogen atoms. Their general formula is CnH2n+1X, where X is a halogen. Their functional group is therefore C-X.

They are used as refrigerants, solvents, pharmaceuticals and anaesthetics but have been restricted due to their link to the depletion of the ozone layer.

C-X bonds are polar due to the halogen being more electronegative than the carbon. The polarity of the bond decreases down group 7.

Van der Waals and permanent dipole-dipole interactions are the intermolecular forces in halogenoalkanes.

When carbon chain length increases, boiling points increase due to RAM increasing and the number of Van Der Waals increasing too.

In branched halogenoalkanes, Van Der Waals are working across a greater distance therefore attraction is weaker and boiling points are lower than an identical unbranched chain.

When the halogen is changed, the boiling point increases down the group due to the effect of a greater RAM  - more VDWs mean more intermolecular forces to break.  

Halogenoalkanes are insoluble in water but soluble in organic solvents like ethanol.

Bonus: free radical substitution reactions in the ozone layer

Ozone, O3, is an allotrope of oxygen that is usually found in the stratosphere above the surface of the Earth. The ozone layer prevents harmful rays of ultraviolet light from reaching the Earth by enhancing the absorption of UV light by nitrogen and oxygen. UV light causes sunburn, cataracts and skin cancer but is also essential in vitamin D production. Scientists have observed a depletion in the ozone layer protecting us and have linked it to photochemical chain reactions by halogen free radicals, sourced from halogenoalkanes which were used a solvents, propellants and refrigerants at the time.  

CFCs cause the greatest destruction due to their chlorine free radicals. CFCs – chloroflouroalkanes – were once valued for their lack of toxicity and their non-flammability. This stability means that they do not degrade and instead diffuse into the stratosphere where UV light breaks down the C-Cl bond and produces chlorine free radicals.

RCF2Cl UV light —> RCF2● + Cl●

Chlorine free radicals then react with ozone, decomposing it to form oxygen.

Cl● + O3 —> ClO● + O2

Chlorine radical is then reformed by reacting with more ozone molecules.

ClO● + O3 —-> 2O2 + Cl●

It is estimated that one chlorine free radical can decompose 100 000 molecules of ozone. The overall equation is:

2O3 —-> 3O2

200 countries pledged to phase of the production of ozone depleting agents in Montreal, leading to a search for alternatives. Chemists have developed and synthesised alternative chlorine-free compounds that do not deplete the ozone layer such as hydroflurocarbons (HFCs) like trifluromethane, CHF3.

SUMMARY

Ozone, found in the stratosphere, protects us from harmful UV light which can cause cataracts, skin cancer and sunburn.  

Ozone depletion has been linked to the use of halogenoalkanes due to their halogen free radicals.  

CFCs were good chemicals to use because they have low toxicity and were non-flammable. The fact they don’t degrade means they diffuse into the stratosphere. 

Chlorine free radicals are made when CFCs are broken down by UV light.

These go on to react with ozone to produce oxygen.

Chlorine free radicals are then reformed by reacting with more ozone.

It is a chain reaction that can deplete over 100 000 molecules of ozone.

There is a 200 country ban on their use and scientists have developed alternatives like hydrofluorocarbons to replace them

Happy studying!

Combusting Alkanes

If you follow this blog, by now you must be thinking, when will we be done with the alkane chemistry? Well, the answer is never. There is still one more topic to touch on - burning alkanes and the environmental effects. Study up chums!

Alkanes are used as fuels due to how they can combust easily to release large amounts of heat energy. Combustion is essentially burning something in the presence of oxygen. There are two types of combustion: complete and incomplete. 

Complete combustion occurs when there is a plentiful supply of air. When an alkane is burned in sufficient oxygen, it produces carbon dioxide and water. How much depends on what is being burnt. For example:

butane + oxygen -> carbon dioxide + water

2C4H10 (g) + 13O2 (g) -> 8CO2 (g) + 10H2O (g)

Remember state symbols in combustion reactions. In addition, this reaction can be halved to balance for 1 mole of butane by using fractions when dealing with the numbers.

C4H10 (g) + 6 ½ O2 (g) -> 4CO2 (g) + 5H2O (g)

Incomplete combustion on the other hand occurs when there is a limited supply of air. There are two kinds of incomplete combustion. The first type produces water and carbon monoxide. 

butane + limited oxygen -> carbon monoxide + water

C4H10 (g) + 4 ½ O2 (g) -> 4CO (g) + 5H2O (g)

Carbon monoxide is dangerous because it is toxic and undetectable due to being smell-free and colourless. It reacts with haemoglobin in your blood to reduce their oxygen-carrying ability and can cause drowsiness, nausea, respiratory failure or death. Applicances therefore must be maintained to prevent the formation of the monoxide.

The other kind of incomplete combustion occurs in even less oxygen. It produces water and soot (carbon).

butane + very limited oxygen -> carbon + water

C4H10 (g) + 2 ½ O2 (g) -> 4C (g) + 5H2O (g)

Internal combustion engines work by changing chemical energy to kinetic energy, fuelled by the combustion of alkane fuels in oxygen. When this reaction is undergone, so do other unwanted side reactions due to the high pressure and temperature, e.g. the production of nitrogen oxides.

Nitrogen is regularly unreactive but when combined with oxygen, it produces NO and NO2 molecules:

nitrogen + oxygen -> nitrogen (II) oxide

N2 (g) + O2 (g) -> 2NO (g)

and

nitrogen + oxygen -> nitrogen (II) oxide

N2 (g) + 2O2 (g) -> 2NO2 (g)

Sulfur dioxide (SO2) is sometimes present in the exhaust mixture as impurities from crude oil. It is produced when sulfur reacts with oxygen. Nitrogen oxides, carbon dioxide, carbon monoxide, carbon particles, unburnt hydrocarbons, water vapour and sulfur dioxide are all produced in exhaust fumes and are also pollutants that cause problems you need to be aware of for the exam as well as how to get rid of them.

Greenhouse gases contribute to global warming, an important process where infrared radiation from the sun is prevented from escaping back into space by atmospheric gases. On the one hand, some greenhouse gases need to continue this so that the earth can sustain life as it traps heat, however, we do not want the earth’s temperature to increase that much. Global warming is the term given to the increasing average temperature of the earth, which has seen an increase in the last few years due to human activity - burning fossil fuels like alkanes has produced more gases which trap more heat. Examples of greenhouse gases include carbon dioxide, methane and water vapour.

Another pollution problem the earth faces is acid rain. Rain water is already slightly acidic due to the CO2 present in the atmosphere but acid rain is more acidic than this. Nitrogen oxides contribute to acid rain although sulfur dioxide is the main cause. The equation for sulfur dioxide reacting with water in the air to produce oxidised sulfurous acid and therefore sulphuric acid is:

SO2 (g) + H2O (g) + ½ O2 (g) -> H2SO4 (aq)

Acid rain is a problem because it destroys lakes, buildings and vegetation. It is also a global problem because it can fall far from the original source of the pollution.

Photochemical smog is formed from nitrogen oxides, sulfur dioxide and unburnt hydrocarbons that react with sunlight. It mostly forms in industralised cities and causes health problems such as emphysema.

So what can we do about the pollutants?

A good method of stopping pollution is preventing it in the first place, therefore cars have catalytic converters which reduce the amount of carbon monoxide, nitrogen oxides and unburnt hydrocarbons come into the atmosphere by converting them into less toxic gases. Shaped like a honeycomb for increased SA and therefore rate of conversion, platinum and rhodium coat ceramic and act as catalysts for the reactions that take place in an internal combustion engine.

As they pass over the catalyst, they react with each other to form less pollution:

octane + nitrogen (II) oxide -> carbon dioxide + nitrogen + water

C8H18 (g) + 25NO -> 8CO2 (g) + 12 ½ N2 (g) + 9H2O (g)

nitrogen (II) oxide + carbon monoxide  -> carbon dioxide + nitrogen

2NO (g) + 2CO (g) -> 2CO2 (g) + N2 (g)

Finally, sulfur dioxide must be dealt with. The first way it is dealt with is by removing it from petrol before it can be burnt, however, this is often not economically favourable for fuels used in power stations. A process called flue gas desulfurisation is used instead.

In this, gases are passed through a wet semi-solid called a slurry that contains calcium oxide or calcium carbonate. These neutralise the acid, due to being bases, to form calcium sulfate which has little commercial value but can be oxidised to produce a more valuable construction material.

calcium oxide + sulfur dioxide -> calcium sulfite

CaO (s) + SO2 (g) -> CaSO3 (s)

calcium carbonate + sulfur dioxide -> calcium sulfite + carbon dioxide

CaCO3 (s) + SO2 (g) -> CaSO3 (s) + CO2 (g)

calcium sulfite + oxygen -> calcium sulfate

CaSO3 (s) + O -> CaSO4 (s)

SUMMARY

Alkanes are used as fuels due to how they can combust easily to release large amounts of heat energy. Combustion is essentially burning something in the presence of oxygen.

Complete combustion occurs when there is a plentiful supply of air. When an alkane is burned in sufficient oxygen, it produces carbon dioxide and water

Remember state symbols in combustion reactions. In addition, reactions can be halved to balance for 1 mole of compounds by using fractions when dealing with the numbers.

Incomplete combustion occurs when there is a limited supply of air. There are two kinds of incomplete combustion. 

The first type produces water and carbon monoxide.

Carbon monoxide is dangerous because it is toxic and undetectable due to being smell-free and colourless. It reacts with haemoglobin in your blood to reduce their oxygen-carrying ability and can cause drowsiness, nausea, respiratory failure or death. 

The other kind of incomplete combustion occurs in even less oxygen. It produces water and soot (carbon).

Internal combustion engines work by changing chemical energy to kinetic energy, fuelled by the combustion of alkane fuels in oxygen. When this reaction is undergone, so do other unwanted side reactions due to the high pressure and temperature, e.g. the production of nitrogen oxides.

Nitrogen is regularly unreactive but when combined with oxygen, it produces NO and NO2 molecules:

Sulfur dioxide (SO2) is sometimes present in the exhaust mixture as impurities from crude oil. It is produced when sulfur reacts with oxygen.

Nitrogen oxides, carbon dioxide, carbon monoxide, carbon particles, unburnt hydrocarbons, water vapour and sulfur dioxide are all produced in exhaust fumes and are also pollutants that cause problems you need to be aware of for the exam as well as how to get rid of them.

Greenhouse gases contribute to global warming, an important process where infrared radiation from the sun is prevented from escaping back into space by atmospheric gases. Some greenhouse gases need to continue this so that the earth can sustain life as it traps heat, however, we do not want the earth’s temperature to increase that much. Global warming is the term given to the increasing average temperature of the earth, which has seen an increase in the last few years due to human activity - burning fossil fuels like alkanes has produced more gases which trap more heat. 

Another pollution problem the earth faces is acid rain. Nitrogen oxides contribute to acid rain although sulfur dioxide is the main cause. 

Acid rain is a problem because it destroys lakes, buildings and vegetation. It is also a global problem because it can fall far from the original source of the pollution.

Photochemical smog is formed from nitrogen oxides, sulfur dioxide and unburnt hydrocarbons that react with sunlight. It mostly forms in industralised cities and causes health problems such as emphysema.

A good method of stopping pollution is preventing it in the first place, therefore cars have catalytic converters which reduce the amount of carbon monoxide, nitrogen oxides and unburnt hydrocarbons come into the atmosphere by converting them into less toxic gases. Shaped like a honeycomb for increased SA and therefore rate of conversion, platinum and rhodium coat ceramic and act as catalysts for the reactions that take place in an internal combustion engine.

As they pass over the catalyst, they react with each other to form less pollution.

octane + nitrogen (II) oxide -> carbon dioxide + nitrogen + water

C8H18 (g) + 25NO -> 8CO2 (g) + 12 ½ N2 (g) + 9H2O (g)

nitrogen (II) oxide + carbon monoxide  -> carbon dioxide + nitrogen

2NO (g) + 2CO (g) -> 2CO2 (g) + N2 (g)

Finally, sulfur dioxide must be dealt with. The first way it is dealt with is by removing it from petrol before it can be burnt, however, this is often not economically favourable for fuels used in power stations. A process called flue gas desulfurisation is used instead.

In this, gases are passed through a wet semi-solid called a slurry that contains calcium oxide or calcium carbonate. Since they are bases, these neutralise the acid to form calcium sulfate which has little commercial value but can be oxidised to produce a more valuable construction material.

Happy studying!

#Thunderstorms are hitting the UK this week – here’s how thunder and lightning happen and some of the chemistry going on during a storm: https://ift.tt/2XUCKZc https://ift.tt/3gJ7ALD

🌻 little habits/things to do more of 🌻

dailies

make your bed. (no, really.)

set your top 3 to-dos for the day.

do your top 3 to-dos for the day. (heh)

stretch.

unpack your bag when you get home.

prepare your things for the next day before sleeping.

skincare. (your basic cleanse and moisturize)

sweep the floor of your bedroom.

talk to your plants. (if you have plants)

update your financial report/expense tracker.

take a good photo.

meditate.

hug at least three people. (seriously.)

weeklies

polish your school shoes.

mop your bedroom floor.

dare i say, laundry. (don’t put it off!)

exfoliate.

take a leisure walk.

review your past week and plan your next week accordingly. (a part of your routine may not be working–try something new)

make a piece of art. (a sketch, a collage, a quote in pretty lettering, a god-awful poem..)

sanitize your gadgets. (whip out the wet tissue and wipe away at your phone, your laptop, your mouse, your earphones–just don’t forget to IMMEDIATELY follow that up with a dry cloth to prevent fogging and short circuits)

watch a TED Talk.

make a new playlist.

monthlies

wash your bag.

wash your shoes.

change the sheets of your bed and your pillows.

clip your nails. (honestly)

wax/shave. (if you want. i just really like how fresh my skin feels after i torture it with razors and wax strips)

wipe your shelves/the tops of your furniture clean. (try to avoid dusting. it just scatters the dirt everywhere. use a damp cloth instead)

see if there’s anything in your storage that you don’t need/want anymore and give stuff away or sell them.

review your month and plan the next one accordingly. (just like your weeks. remember to refer to your Life Goal/Year’s Goals page)

finish reading at least one book. (and review it!)

discover new songs.

- 🍂