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Topic: Result of adding the following reagents and what structures they form?  (Read 3404 times)

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Offline Kobsessed

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Result of adding the following reagents and what structures they form?
« on: March 10, 2009, 12:20:08 AM »
Hello, for one of my pre-lab assignments I've got a question I have no idea how to answer. We are given a flowchart. ethyl 4-aminobenzoate + naphthalene and their structures are shown at the top. Underneath, there is a reagent beig added which is 2-methoxy-2-methylpropane. Why is this being added?
Then, under that, we add 5% HCl, to make it acidic I'm assuming. So by adding the HCl, suddenly the flow chart divides into two boxes and I have to draw a structure for each. What exactly is this structure? Underneath one of these boxes, we are to add 10% NaOH (to make it basic?) and so this forms a different structure and I've got to draw that one too. I have no idea what to do here. I did manage to here some people mention something about one takes H+ and one removes H+ but I didn't understand that.

So anyone know how to help me out? Thanks!
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Offline sjb

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Re: Result of adding the following reagents and what structures they form?
« Reply #1 on: March 10, 2009, 05:54:47 AM »
I assume that you have a theoretical mixture of the ester and naphthalene. The 2-methoxy-2-methylpropane is probably just a solvent (http://en.wikipedia.org/w/index.php?title=Methyl_tert-butyl_ether&oldid=271732170), to ensure mixing.

What happens when you add dilute acid to the ester? To naphthalene?
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Offline Kobsessed

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Re: Result of adding the following reagents and what structures they form?
« Reply #2 on: March 10, 2009, 09:50:35 PM »
Quote from: sjb on March 10, 2009, 05:54:47 AM
I assume that you have a theoretical mixture of the ester and naphthalene. The 2-methoxy-2-methylpropane is probably just a solvent (http://en.wikipedia.org/w/index.php?title=Methyl_tert-butyl_ether&oldid=271732170), to ensure mixing.

What happens when you add dilute acid to the ester? To naphthalene?

Thank you for answering! Hmm ok. So I'm guessing this whole thing is to seperate the two mixtures. I knoww the amino group will make the ethy compund soluble in HCl and so it forms ethyl 4-amino benzoate hydrochloride. And then adding NaOH to that gives me the ethyl all over again. The reason we don't use this first is because well I'm guessing due to the fact that there are no acidic functional groups before adding HCl. So yeah that's great.

Now I'm stuck on Naphthalene. So I'm guessing it is soluble with HCl and therefore yields a reaction. Not sure what this new compund is called though. 
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Offline sjb

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Re: Result of adding the following reagents and what structures they form?
« Reply #3 on: March 11, 2009, 05:07:26 AM »
Almost, but not quite.  ;)

How soluble is naphthalene in acid? In organic solvents (like your 2-methoxy-2-methylpropane, aka MTBE)?

S
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