Solvents and Solvent Effects in Organic Chemistry (Fourth, Updated and Expanded Edition)

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Polar Aprotic? All About Solvents.

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Steric Hindrance is Like a Fat Goalie. And to be honest, a lot of instructors myself included are less than consistent about when to include solvents and when not to. So the whole exercise can come across as somewhat arbitrary: when do you know when to include the solvent? A solvent is a liquid that serves as the medium for a reaction.

Solvents and Solvent Effects in Organic Chemistry, 3rd, Updated and Enlarged Edition

It can serve two major purposes:. There are two direct ways of measuring polarity. A second comes from directly measuring the dipole moment. Polarity is a continuum. However diethyl ether Et2O is a common solvent for Grignard reactions; its lone pairs are Lewis basic and can help to solvate the Mg cation. These solvents have moderately higher dielectric constants than the nonpolar solvents between 5 and Their high polarity allows them to dissolve charged species such as various anions used as nucleophiles e. For our purposes these solvents do not participate in reactions.


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Polar protic solvents tend to have high dielectric constants and high dipole moments. Furthermore, since they possess O-H or N-H bonds, they can also participate in hydrogen bonding. These solvents can also serve as acids sources of protons and weak nucleophiles forming bonds with strong electrophiles. They are most commonly used as the solvent for their conjugate bases.

These types of solvents are by far the most likely to participate in reactions. There are many examples too many to list where a polar protic solvent such as water, methanol, or ethanol can serve as the nucleophile in a reaction, often when a strong electrophile such as an acid is present. So if you see this type of solvent, be on the lookout. Something that eludes me: why is the dipole of chloroform smaller than that of DCM?

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Since dipole moment is based on magnitude and separation of charges, I imagine the reason is that the 3 C-Cl bonds cancel each other out more than the 2 C-Cl bonds. Perhaps the C-H bonds provide additional electron density that allows for greater overall polarization of the molecule.

Substitution Reactions

I would have thought that it is because Carbons 2p2 electrons are being shared between more Chlorines in the Chloroform you have a weaker dipole moment between each of the C-Cl bonds than in DCM. So you have a greater dipole moment in DCM. Dipole moment of chloromethane is 1. Further Chem: Drawing out the molecular orbital diagrams may help as it would show which electrons enter which sub shell and that would show you if it is entering a higher or lower energy level.

For F though your point may be valid, it can be verified if the order of polarity of Fluoro-methanes are reverse of Cl substituted methanes.

Polar Protic Solvents VS Polar Aprotic Solvents for SN1 and SN2 Reactions

Because Hydrogen is more electropositive than Carbon the dipole moment is lower. For example, compare the electronegativity between HCl and CCl bonds. I think it is because the inductive effect of the three Chlorines on chloroform cancel out much of the outward negative dipole while with DCM, there are only two chlorines to withdraw electrons, thus less cancelation of the inductive effect.

Back to vector sums, folks. Its doesnt matter 3 Cl- are withdrawing electron density…. Important to make sure inversion is there! Exactly, never thought to compare acid strength to polarity of solvents. James, your work on this topic solvents very amazing. Hats of you.


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  6. If bromine is added to chloroform, I believe the bromine should stay the diatomic elemental color because chloroform is saturated and therefore will not react, it should react the same with DCM. The examples for the uses of each of the solvents were exactly what I needed help with and were indeed quite helpful.

    Those would be areas on interest to expand on. Thank you! If you want to run a polar content, run it with a polar solvent as the polarities are the ones that determine the interactions.. Why is this? Great question Elon. The dipole moment is low because the displaced charges between the HO and CO bond in acetic acid can dampen or stabilize the partial charge generated.

    A dipole vector points away from H and toward O while another points away from C and toward O. The negative end of the HO vector is closest to the positive end of the CO vector hence the dampening of the induced charge. This would lead to the conclusion that the sum of the charges, q in acetic acid containing two highly electronegative atoms is smaller than q in the alcohols containing only one highly electroneative atom. Hence, the larger dipole moment in acetic acid but smaller in H2O which is where the dipole vectors are aligned in a way that adds the magnitude of the vectors and results in the higher 1.

    How is the electrical conductivity change with polarity? If the voltage is high, can polar aprotic solvent also electrolysis? As far as I know, Hexafluoroisopropanol HFIP is a good solvent for polymers, even though it is a polar protic solvent. The best property of HFIP as I know is it can dissolve either polar in non-polar molecule or non-polar in polar molecule. I used it for making the polymer blending between polyester and protein. If someone know about that, please give me some explanations.

    Using a polar protic solvent increases the rate of the reaction right?

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    Well, how am I suppose to know whether to use a type 1 or type 2? It is more polar than hydrocarbons, but is still not miscible at all with water. Why protic? Hi Roger — the rate limiting step will be formation of the free carbocation. The rate will be increased if we use a solvent with a high dielectric constant i. Solvents with high dielectric constants also tend to be polar protic e. However, polar protic solvents are not a requirement for HBr addition. I would be wary of using a polar protic solvent because it can act as a nucleophile, trapping the carbocation.

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    James, could you enlighten me as to what that might mean in terms of its ability to dissolve various types of chemical blockages? Thanks, Roy. The reaction takes place when ether is used as a solvent!!!!!!! Well, this could be happening several different ways, but one pathway is reductive formation of the methyl anion followed by substitution. Another is formation of methyl radical and subsequent coupling of two radicals termination. Wurtz coupling. Not a very high yielding reaction.

    Which would serve better in an SN2 mechanism?