This experiments enables you to different a solid-phasemixture consists of (i) 2-methoxynaphthalene, (ii)m-nitroaniline,and (iii) benzoic acid utilizing Separatory Funnel extractions. Since each of these chemicals have similar solubilities in water and also ether, friend can result a separation their chemical properties. For example, benzoic mountain is insoluble in water yet the benzoate ion is dissolve in water. Therefore, under neutral conditions, the benzoic will certainly partition right into the ether layer. Adding NaOH will neutralize the benzoic acid producing the benzoate ion, which currently goes into the aqueous layer, leaving other other 2 organic compound in the ether. Likewise, nitroaniline is not soluble in neutral or an easy conditions, but is dissolve in acidic solutions. Making the fluid in the Separatory Funnel acidic will allow the nitroaniline to be positive charged, and it will currently partition right into the aqueous layer. Isolating the aqueous layers permit you to crystallize the benzoic acid and nitroaniline as explain in this protocol. Final analysis of the isolated chemicals will be done making use of melt allude analysis. You will also need to determine a percent yield because that each.

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Benzoic mountain m-nitroaniline1 2-methoxynaphthalene
1para or meta-nitroaniline might be supplied for this experiment


In experiments Ia and also Ib youpurified a heavy by choosing a solvent thata particular chemical is soluble in, however which another remainsinsoluble(e.g., acetone dissolved aspirin yet not the NaCl or silica) and by utilizing the method of re-crystallization you to be able to isolate benzoic acid in pure type away native contaminants. However, over there aremany timeswhen neither of these approaches are be suitable because girlfriend mayneedto isolate 2 or an ext solids native the exact same mixture that have very similar physical or chemistry properties. For example, and both solids areorganicin nature, with similar solubility properties, or once the liquids youaretrying to separate boil at virtually the very same temperature (distillation isatechnique us will usage in a later on experiment). Solventextraction isa procedure that will work-related well in plenty of of these cases. Throughout anextraction,one solvent is used to dissolve (or partition) one or an ext of thecomponentsof the mixture, leaving other components behind (in the solid phase,theliquid phase, or in another solvent). In this experiment we will certainly beworkingwith "liquid-liquid" extractions, yet the general values will bethesame because that "solid-liquid" extractions together well.

Zubrick makes the importantdistinction in between "extraction" and "washing".While the same series of speculative steps are generally used come carryoutboth of these techniques, and they usage the exact same theory, the maindifferenceis the in an extraction you are relocating a problem you want to keepintoa new solvent, if in washing friend are moving a substance you willthrowaway into a new substance. In future experiment you may be instructedto"extract the product mixture v 3, 10-mL portions, the ether," or"washthe ether extracts v 10% sodium bicarbonate, and also then with water."Theseinstructions i think you recognize the difference between extractionandwashing.

In this experiment you will certainly begiven a mixture comprise 2-methoxynaphthalene, m-nitroanilineand benzoic acid. The very first step in the separation will be come dissolvethe whole mixture in one organic solvent (diethyl ether). You will certainly usethe chemical and physical properties of these compounds to determinehow to separate them in pure form using extractions (and washings,where necessary), and also isolate the m-nitroanilineand benzoic mountain in heavy form. Monitor the guidelines provided in chapter15 the Zubrick in determining the solvents you will certainly use, the order inwhich you carry out the extractions, and also the methods you will usage to geteach compound earlier into the heavy form.

Day1 execute separatory funnelextractions of chemistry mixture isolation pure benzoic acid (from basic extraction of the ether layer) isolation purem-nitroaniline (from acidic exploit of the ether layer) Day2 Quantitate recoveredchemicals (determine percent yield) identify melt pointsfor recovered chemicals



2-methoxynaphthalene is anirritant — wear gloves while taking care of it. m-nitroaniline(or p-nitroaniline)is one irritant, and is very toxic —wear gloveswhile taking care of it; take special care not come ingest any type of of that or toinhale the vapors or dust. Benzoic acid is one irritant— undertake gloves while taking care of it. Hydrochloric mountain solutionis corrosive and also toxic — wear gloves while taking care of it. sodium hydroxide systems iscorrosive and toxic — wear gloves while taking care of it. Diethyl ether (most oftenjust described as ether) is extremely volatile with a boiling point ofabout 35oC,and very flammable — handle with care and pour from thebottle in the hood.

To perform the experiment, obtain about 3 grams (2.5-3.0 grams is acceptable) of the hard mixtureconsisting of about equal portions of:

2-methoxynaphthalenem-nitroanilinebenzoic acid

You will be separating native the above mixture pure benzoic acid and also pure m-nitroaniline.

Under typical conditions, all 3 of your organic compounds will dissolve in the organic layer (the diethyl ether), not the aqueous layer. The only means to different the necessary compounds native each other is to rely on your chemical properties, not simply physical properties. To this end, you should always remember the neutral necessary compounds perform not dissolve come a an excellent extent in aqueous solutions. Alternatively, charged organic compounds will often dissolve in aqueous solvents since they are ions. Conversely, neutral essential compounds dissolve in essential solvents (e.g., diethyl ether) whereas charged organic compounds will certainly not dissolve (or continue to be dissolved) in necessary solvents.

that is possible to pressure an organic compound, the is charged, out of the necessary phase into the aqueous phase. This process is commonly performed using a Separatory Funnel. Once a compound leaves one phase and also goes into the various other phase, this procedure is referred to as partitioning. For example, as soon as the benzoate ion, derived from benzoic acid, leaves the ether phase and goes right into the aqueous phase, we refer to this as partitioning right into the aqueous phase.

The figures listed below show how this is excellent in order to isolate various compounds based upon their acid-base properties. Benzoic acid is dissolve in ether, but when neutralized and also converted into benzoate ion, it is now soluble in water, so will certainly partition into the lower aqueous phase, leave uncharged organic compounds in the ether. When the aqueous layer is isolated, benzoic acid is easily isolated as soon as the benzoate ion is converted ago into benzoic acid complying with the addition of 6 M HCl.


m-nitroaniline is dissolve in ether, even when the aqueous class is basic, because a base remain base in base. However, as soon as a systems of 1 M HCl is included to the Separatory Funnel, the amino team accepts a proton i beg your pardon produces a charged molecule. This fee molecule then partitions into the aqueous layer, and also can it is in collected. Once the aqueous layer has actually 6 M NaOH added to you, the m-nitroaniline is regenerated, and since it is currently insoluble in water, you have the right to collect it as a solid.


The general dominance you should remember is the uncharged essential compounds remain in the essential (e.g., ether) layer. Fee organic compound partition right into the aqueous layer. The doesn"t issue whether the organic compound acquires a positive or an unfavorable charge, it will partition into the aqueous layer, out of the essential layer. Mountain (i.e., benzoic acid) are converted right into their negatively charged ion in the visibility of base, and partition right into the aqueous layer. Bases (e.g., m-nitroaniline, i m sorry is a base because it is a proton acceptor) end up being positively charged when reacted v an acid, and also this positively fee ion will currently partition into the aqueous layer. Fee molecules partition into the aqueous layer and uncharged molecules partition into the essential layer.

Isolation that Benzoic Acid

utilizing a powder funnel (a plastic funnel v a more comprehensive opening and also that fits in the ground-glass opened of her Separatory Funnel) include all of her mixture to the Separatory Funnel. Add the following to the Separatory Funnel:

30 mL of diethyl ether (the ether bottle should be kept in the hood and constantly replace the lid after dispensing)30 mL 1.0 M NaOH

By adding the NaOH come the organic link mixture (with diethyl ether), girlfriend will convert the benzoic acid (uncharged) right into sodium benzoate (negatively charged), which is currently soluble in aqueous solutions. The various other organic compounds, which stay neutral in simple solutions continue to be uncharged in the diethyl ether layer. The negatively fee benzoate ion now partitions into the lower aqueous layer once you shiver the components of the Separatory Funnel. Be details that you extensively mixture the materials of the Separatory Funnel to permit effective partitioning the the benzoate ion right into the aqueous layer.

when you check out the illustration of two distinctive layers in the Separatory Funnel (upper essential layer and also lower aqueous layer), you can collect the lower aqueous class which has the benzoate ion. To collection the lower layer, first remove the ground-glass stopper, and also then open the stopcock valve. Let the reduced aqueous layer drain out until the height organic layer simply reaches the stopcock worth opening. Nearby the stopcock valve, and also prepare to isolation the nitroaniline.

In stimulate to collection your benzoic acid, you require to transform the benzoate ion (which is completely soluble in water) back to benzoic mountain (which is mainly insoluble in water). To result this conversion, friend must an initial add mountain to the benzoate solution, which will certainly then enable benzoic mountain to form.

using the 6 M HCl solution include enough mountain to convert every one of the benzoate ion come benzoic acid. As a an initial approximation, you will need around 5 mL that the 6 M HCl to neutralize her solution. Keep adding 6 M HCl until the equipment is acidic, based on litmus paper. When you think you having actually an acidic systems add about 2 mL much more 6 M HCl, due to the fact that you cannot have actually too much acid. A tiny phrase you can remember is: "acid stays acid in acid."

collection your hard benzoic acid over using vacuum filtration with a typical Buchner Funnel filtration setup. Because that this certain experiment, do not store the filter file in the stove as it will certainly decompose in ~ a high temperature once the paper is acidic. So, simply scrape your solid benzoic acid into an evaporating food (or 100-mL beaker) and also place that in the drying oven until the following lab period.

Isolation the m-Nitroaniline

after you have actually removed the benzoic acid from the ether class (by the enhancement of NaOH above), you are left with an ether layer quiet containing the nitroaniline and methoxynaphthlene. In order to effect the removal of the nitroaniline, you depend on the reality that nitroaniline features as a Bronsted-Lowry base (proton acceptor) lot like how ammonia (NH3) accepts a proton to end up being the ammonium ion (NH4+). In the case of the nitroaniline accepting a proton, it i do not care the nitroanilinium ion. Therefore, when you add a solution of 1 M HCl to the ether layer, you transform the neutral nitroaniline right into the charged nitroanilinium ion, which deserve to then partition right into the acidic aqueous layer.

include 30 mL that the 1 M HCl systems to the Separatory Funnel. Adhering to this addition, change the ground-glass stopper

Caution:After using ether, store the lid on the ether bottle as soon as not in use.

Dissolve the solids in theseparatory funnel by adding the stopper and also mixing thoroughly. You cando her separatory funnel extractions in the rap (outside of the hood),but any type of open containers with ether have to be handled in the hood (you canremove the stopper come the separatory funnel in the laboratory withoutproblem).

Using known chemical andphysical properties because that these compounds develop an extraction system inorder to different the three solids, and also to isolate each link insolid form. For example, what are the physical properties ofthese compounds, what are their solubilitiesor their lack ofsolubility in specific solvents (e.g., in ether or aqueous solvents).The extraction and also washing solvents obtainable are: water; 10% sodiumbicarbonate solution; 6 M sodium hydroxide solution; 6 M hydrochloricacid solution. Usage 6 M HCl or 6 M NaOH to neutralize your aqueous solutions built up containing one of two people the benzoate ion (extraction in base) or the nitroanilinium ion (extraction in acid) in the aqueous solutions.

as soon as you have actually successfullyextracted one of two people the m-nitroanilineor benzoic acid into one that the aqueous extraction solvents, friend willneed come isolate the chemical in pure heavy form. Every one of theorganic chemicals will certainly be initially soluble in the necessary solvent(diethyl ether). Because that example, how deserve to you pressure the benzoicacid to it is in partitioned (extracted) into one the the extraction or washsolutions because that purification? when it is in the appropriatesolution as a dissolved solute, how have the right to you convert it into aninsoluble solid to isolate and also characterize?

after ~ you have actually isolated boththe m-nitroanilineand benzoic acid in pure forms, you have the right to discard the staying organicliquid, comprise the 2-methoxynaphthalene in the organic liquid wastecontainer.

How lot m-nitroanilinedid friend recover? how much benzoic mountain did friend recover? Whatare the physical properties of this compounds that you observed(color, crystal shape, etc.)? What is the melting allude foreach these compounds? how do these worths compare to the literaturevalues?Do girlfriend think the you isolated this compounds in pureform, based on the observed melting points?

Guidelinesfor law separatory funnel extractions:

Read chapters 15 and 16 in Zubrick.

Acid and Base Solution info Acids provides of acid solution Base offers of simple solutions

6 M HCl

Use this solution onlyto neutralize a simple solution never for extractions 6 M NaOH Use this equipment onlyto neutralize an acidic solution never for extractions
1.0 M HCl Use this systems forwashes and also extractions (e.g., in a separatory funnel) never forneutralizations 1.0 M NaOH Use this systems forwashes and also extractions (e.g., in a separatory funnel) never forneutralizations
10%NaHCO3(sodium bicarbonate solution) can be used to neutralize one acidicsolution in ~ a separatory funnel, if you desire to finish up through a solutionnear neutral pH. To get rid of the NaHCO3,simply use 2-3 DI water washes, efficiently washing the etherlayer and also getting rid that the bicarbonate ion. Perform not use sodium bicarbonate equipment to neutralize an acidic equipment not in a separatory funnel.

CheckingpH (acidity or basicity) the a solution.

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Litmus record is one effectiveand inexpensive an approach to determine if a systems is either simple oracidic. Usage litmus paper in this experiment to recognize if you haveproduced one acidic or straightforward solution.

Red litmus paper is offered tomonitor for an easy solutions (red file turns blue in base) Blue litmus file is used tomonitor because that acidic solutions (blue paper turns red in acid)

Chemicals and also Equipment supplied for Experiment
6 M HCl 6 M NaOH 1.0 M HCl 1.0 M NaOH 10% NaHCO3 Diethyl ether Benzoic acid m-nitroaniline 2-methoxynaphthlene separatory funnel

Chemicals, Reagents, and Supplies compound MW quantity mmol mp bp density ηD msds Benzoic Acid 122.12 --- --- 122.4 249.4 1.2659 --- view m-Nitroaniline 138.12 --- --- 114 331.7 1.424 --- view 2-methoxynaphthlene 158.2 --- --- 73-75 274 n/a --- view Diethyl ether 74.12 30 mL --- -116.3 34.6 0.7134 --- view HCl view NaOH view link g/mol grams or mL 10-3 M oC oC g/mL ηD msds