Your Question About Easy Weight Loss

Susan asks…

What safety precautions should one take when using chlorinated solvents for extraction?

Also, what is the practical advantage of using dichloromethane (density=1.325g/ml) over diethyl ether (density=0.706glml) for extracting organic compounds from an aqueous solution using a separatory funnel?

weight loss cardiff answers:

The lab should be well ventilated, as chlorinated solvents are toxic and induce nausea and drowsiness.

Since CH2Cl2 is denser than water, the organic layer will be the lower layer. This can be drained off and more, fresh solvent can be added to the separatory funnel for a 2nd extraction.

If diethyl ether is used, the organic layer is the upper layer. The aqeuous layer has to be drained off, the organic layer decanted out of the top and, if a 2nd extraction is to be done, the aqueous layer has to then be returned to the separatory funnel. More transfers of layers means more losses of material.

Donald asks…

How to do you separate a mixture of benzoic acid and 2-naphthol?

Do we used sodium bicarbonate or diethyl ether?

weight loss cardiff answers:

First dissolve a few grams of the mixture in diethyl ether.

Next, extract the benzoic acid into an aqueous layer by adding saturated NaHCO3 to the ether solution in a separatory funnel. This should be done 3 times with small amounts of the saturated NaHCO3 solution. The benzoic acid will react with the NaHCO3 to form a salt that is soluble in the aqueous phase. The aqueous phase will be on the bottom because water is more dense than diethyl ether. Remember to vent the extraction flask often to reduce pressure due to CO2 gas being released in the chemical reaction. 2-naphthol will not dissolve in saturated NaHCO3.

Reaction: C6H5COOH(aq) + HCO3^-(aq) –> C6H5COO^-(aq) + CO2(g) + H2O

Recover the 2-naphthol by removing the ether. If you did a good job of extracting the solid should be fairly pure. You can check this by obtaining a melting point of the product after drying.

Recover the benzoic acid by adding concentrated HCl (caution) to the aqueous solution. The volume of acid you add depends on the amount of benzoic acid you have in the aqueous phase.

Reaction: C6H5COO^-(aq) + H3O^+(aq) –> C6H5COOH(s) + H2O(l)

The pH of the solution can be checked using pH paper as you add more concentrated HCl (add drop by drop) When the pH of the solution reaches about 1 then you can stop adding the acid and cool down the benzoic acid solution in an ice water bath. After the solution is cooled to about 0 degrees Celsius then you should use vacuum filtration to recover the product. Allow the product to dry in your equipment cabinet by leaving the filtered solid on a watch glass.

Hope this is helpful to you. JIL HIR

Ruth asks…

Solubility Tests – How does a solubility test confirm the presence of an acid or a base.?

I did an extraction experiment of an acid/base from a neutral. We first had to determine whether an acid or a base was present. So how does the solubility test determine that? The test was done in diethyl ether (which my base dissolved in), water, HCl, and NaHCO3.

Thanks!

weight loss cardiff answers:

Acids are more easily dissolved in basic solution, bases are more easily dissolved in acidic solution.

Dissolving is an equilibrium reaction so partial solubility in one of the solutions will give an indication. If your unknown did not fully dissolve in acid or base this may be just an indication it is not a strong acid/base. Dissolving in diethyl ether is just an indication of the organic nature of your unknown. Details of solubility testing in this website [1]

Good luck 🙂

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Your Question About Easy Weight Loss

Mark asks…

Other than THF and diethyl ether, what could one use as a solvent for a Grignard? Why are these suitable?

So THF and diethyl ether are both slightly polar but why is that important? I need to know other solvents that could be used for Grignard and what would make a bad solvent and why? I’m guessing a nonpolar solvent would make a bad solvent, or maybe something very polar and thus easier for water to dissolve in? Help!

weight loss cardiff answers:

You’re partly right, a nonpolar solvent wouldn’t work. The Grignard reagent is polar and would not be very soluble in a nonpolar solvent.

To see what kind of polar solvents work best, first remember that the Grignard reaction proceeds through an SN2 mechanism. Your Grignard reagent has a dipole moment, (δ−)R−(δ+)MgBr. That partial negative charge turns the R group from a bad nucleophile to a strong nucleophile, which SN2 needs. But it also makes it a strong base. Because of that, we have to be careful with our solvent. If the solvent we use is even a little bit acidic, some of the Grignard reagent will be diverted into an acid-base side reaction with the solvent, instead of the desired nucleophilic substitution.

So, to enhance a reagent’s nucleophilicity for SN2, we need to use a solvent that is polar, but cannot act as an acid. THF and Et2O fit this description; they have dipole moments but don’t contain acidic hydrogens. Since they won’t give up H+ (a proton), we call this type of solvent a “polar aprotic” solvent.

Grignard reagents in particular are highly reactive toward many polar aprotic solvents, further reducing the number of solvents that will work. For instance, your Grignard reagent would attack an acetone solvent, (CH3)2C=O, since it contains a ketone. You’re basically forced to use an ether solvent with Grignard. So, another ether solvent you might use for Grignard is dibutyl ether.

Short, cram night before the test version:
1) Grignard is SN2
2) polar aprotic solvents favor SN2
3) Grignard side-reacts with solvents other than ethers

Laura asks…

Is benzoic acid more soluble in water or diethyl ether?

When both water and diethyl ether were added to benzoic acid, which layer(ie the organic or aqueous layer) can the benzoic acid can be found.
i am also curious that if benzoic acid is more soluble in diethyl ether, is it due to the 6 carbon chain of the benzoic acid?
C6H5coo- soluble in water?

weight loss cardiff answers:

Benzoic acid is more soluble in diethyl ether than water.

So benzoic acid would be in the organic layer.

Bear in mind that ether is less dense than water, so the extract would be on top.

Benzoic acid is more soluble in ether because the benzene ring is nonpolar, aye.

Benzoate salts are water soluble, though, because water is better able to stabilize the negative charge on the oxygen.

Maria asks…

what is the difference Between Ethyl Ether and Diethyl Ether?

i was in chemistry the other day and we were talking about Ether
and i was curious what’s the difference between the two.

weight loss cardiff answers:

Nothing, they represent the same compound. Diethyl ether is the correct IUPAC name for the compound composed of an oxygen attached to two ethyl groups. Ethyl ether is a common name for the same compound. Not technically correct, but widely understood to mean diethyl ether.

Note that sometimes, this compound is also refered to simply as “ether”.

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