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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!

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Covalent and Dative Bonds

Covalent and dative (sometimes called co-ordinate) bonds occur between two or more non-metals,  e.g. carbon dioxide, water, methane and even diamond. But what actually are they?

A covalent bond is a chemical bond that involves the sharing of electron pairs between atoms. They are found in molecular elements or compounds such as chlorine or sulfur, but also in macromolecular elements and compounds like SiO2 and graphite. Covalent bonds are also found in molecular ions such as NH4+ and HCO3-.

Single covalent bonds have just one shared pair of electrons. Regularly, each atom provides one unpaired electron (the amount of unpaired electrons is usually equal to the number of covalent bonds which can be made) in the bond. Double covalent bonds have two shared pairs of electrons, represented by a double line between atoms, for example, O=C=O (CO2). Triple covalent bonds can also occur such as those in N ≡ N.

Dot and cross diagrams represent the arrangement of electrons in covalently bonded molecules. A shared pair of electrons is represented by a dot and a cross to show that the electrons come from different atoms.

Unpaired electrons are used to form covalent bonds as previously mentioned. The unpaired electrons in orbitals of one atom can be shared with another unpaired electron in an orbital but sometimes atoms can promote electrons into  unoccupied orbitals in the same energy level to form more bonds. This does not always occur, however, meaning different compounds can be formed - PCl3 and PCl4 are examples of this.

An example where promotion is used is in sulfur hexafluoride (SF6). The regular configuration of sulfur atoms is 1s2 2s2 2p6 3s2 3p4. It promotes, as shown in the diagram (see excited state), two electrons: one from the 3s electrons to the 3d orbital and one from the 3p to the 3d. Therefore there are 6 unpaired electrons for fluorine atoms to join. It has an octahedral structure.

An atom which has a lone pair (a pair of electrons uninvolved in bonding) of electrons can form a coordinate bond with the empty orbital of another atom. It essentially donates an electron into this orbital which when formed, acts the same as a normal covalent bond. A coordinate bond therefore contains a shared pair of electrons that have come from one atom.

When ammonia reacts with a H+ ion, a coordinate bond is formed between the lone pair on the ammonia molecule and the empty 1s sub-shell in the H+ ion. An arrow represents the dative covalent bond (coordinate bond). Charges on the final ion must be showed.

Summary

A covalent bond is a chemical bond that involves the sharing of electron pairs between atoms. They are found in molecular elements or compounds as well as in macromolecular elements and compounds. Also found in molecular ions.

Single covalent bonds have just one shared pair of electrons.  Double covalent bonds have two shared pairs of electrons, represented by a double line between atoms. Triple covalent bonds can also occur.

Dot and cross diagrams represent the arrangement of electrons in covalently bonded molecules. A shared pair of electrons is represented by a dot and a cross to show that the electrons come from different atoms.

Unpaired electrons are used to form covalent bonds - they can be shared with another unpaired electron in an orbital but sometimes atoms can promote electrons into unoccupied orbitals in the same energy level to form more bonds. This does not always occur, however, meaning different compounds can be formed.

An example where promotion is used is in sulfur hexafluoride (SF6). 

An atom which has a lone pair (a pair of electrons uninvolved in bonding) of electrons can form a coordinate bond with the empty orbital of another atom.

 It donates an electron into this orbital which when formed, acts the same as a normal covalent bond. A coordinate bond therefore contains a shared pair of electrons that have come from one atom.

When ammonia reacts with a H+ ion, a coordinate bond is formed between the lone pair on the ammonia molecule and the empty 1s sub-shell in the H+ ion. An arrow represents the dative covalent bond (coordinate bond). Charges on the final ion must be showed.

finally, some content! this was a quick info graphic I drew up on Procreate to revise for my ochem test tomorrow. disclaimer: I used information from this source (https://www.masterorganicchemistry.com/2010/05/24/imines-and-enamines/) since my own notes are based off lectures I received at my university that I’m not really allowed to share without heavy modification.

general post disclaimer: I’m an undergraduate student studying biochemistry and genetics. Posts are made for the purposes of education, revision and aesthetics. Not all the content I produce can be taken as entirely accurate and I do not take responsibility for errors made as a result of using this resource. Always consult course textbooks and lectures to aid in your specific learning outcomes. Do not repost without the original caption citing any extra references I used to make this post or remove my watermark. Other posts can be found on my blog as-studypeach@tumblr.com. Any problems, feel free to get in touch via my messages.

Master Organic Chemistry

Imines and Enamines

Imines are the nitrogen analogues of aldehydes and ketones, containing a C=N bond instead of a C=O bond. They are formed through the dehydra

Just a meme

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Alkanes: Crash Course Organic Chemistry #6:

Alkanes are kind of the wallflowers of organic chemistry, but they still have important functions in the world around us. In this episode of Crash Course Organic Chemistry we’re building our knowledge of organic molecules by learning all about these so called couch potatoes from how they are separated from crude oil to how to use Newman projections to predict torsional strain and steric hinderance. We’ll also learn the names of some common conformers and get an introduction to cycloalkanes. 

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