[Alex_426]

If anyone could help point me in the right direction, I've been at this for many hours and I can't figure out how! Thank-you!
 
Propose a mechanism for the synthesis of Phthalic acid. Taking into account that you have the following organic reactants and any inorganic reactants, gases and material that you need.

We have only learned the following reactions so I think I'll have to stick to these for the midterm: Electrophilic addition reactions (hydrogen halides, hydrogen bromide in the presence of peroxide, addition of halogen-Cl2 or Br2, Acid catalyzed addition of h20 and alcohols, oxymercuration-reduction, alkoxymercuration-reduction, hydroboration-oxidation, and addition of H - H2 and Pt/c etc. And some alkyne reactions: addition of halides, hydrogen bromide with peroxide, addition of halogens, water¬haydroboration-oxidation, addition of hydrogen and removal of a proton followed by alkylation.

I know how to add the OH group but I have to idea how to add a double bonded oxygen, I know how to get there from an alkyne but not an alkene and we haven't been given reactions to turn the alkene into an alkyne, just vice versa.

I imagine I could take away the H from the OH group which could leave me with a negative O but I don't know why it would make sense to do that without adding a Halogen. Thank-you!

[sjb]

If anyone could help, I've been at this for many hours and I can't figure out how! Thank-you!
 
Propose a mechanism for the synthesis of Phthalic acid. Taking into account that you have the following organic reactants and any inorganic reactants, gases and material that you need.

We have only learned the following reactions so I think I'll have to stick to these for the midterm: Electrophilic addition reactions (hydrogen halides, hydrogen bromide in the presence of peroxide, addition of halogen-Cl2 or Br2, Acid catalyzed addition of h20 and alcohols, oxymercuration-reduction, alkoxymercuration-reduction, hydroboration-oxidation, and addition of H - H2 and Pt/c etc. And some alkyne reactions: addition of halides, hydrogen bromide with peroxide, addition of halogens, water¬haydroboration-oxidation, addition of hydrogen and removal of a proton followed by alkylation.

OK, what's the structure of phthalic acid?

[Alex_426]

This is what the profesor wrote exactly: Phthalic acid (2-carboxybenzoic). Thanks!

[Alex_426]

The drawing of the structure was not given. I assumed it was this, maybe I was wrong.. http://en.wikipedia.org/wiki/Phthalic_acid

[Alex_426]

PS. original image was cut off so I added another to complete it 

[Babcock_Hall]

It is a forum rule that you must show an attempt first, before we can help you.  I generally like to work synthesis problems backwards, but it sometimes also helps to have a starting material.  Did the problem suggest a starting material?

[Alex_426]

Yea I know it's a rule, that's what I was trying to say by saying what I tried. Guess ill draw it out next time  I think I figured it out though, ozonolysis and then addition of an alcohol. Thank-you Babcock_Hall!

[Babcock_Hall]

I think you are taking a relatively simple problem and making it more difficult.

[Alex_426]

I can't use reactions that lead me straight to a carboxylic acid because we haven't learned that yet. Is that what you're referring to or were you thinking there was another way?

[Babcock_Hall]

Suppose you started with benzene.  What groups can you add to this ring?

[Alex_426]

I can just react one of the compounds that they give me that has two CH=CH2 groups attached to the benzene ring with 1. O3, 78° C 2. H202 and then my C-H bonds that are sp2 bonded are replaced with OH and I have the double bonded oxygen! Right?

But let's see I can do an HX reaction which would add an H and a Br/Cl, I can add Br again but with peroxide which would be anti markovnikov, I can add two halogens or in the presence of H2O add OH and Br/Cl. Also an -OH or -OCH3 group and an H, H2 or an OH added anti markovnikov. With the -OCH3 group i could also add more CH2 groups.

Adding the OH group seemed easy to me but I couldn't figure out anymore of the process from there.

[Babcock_Hall]

Do you know how to add a methyl group?

[Alex_426]

Only as part of an -OCH3 group or to an alkyne using NaNH2 and RCH2Br

[sjb]

I can just react one of the compounds that they give me that has two CH=CH2 groups attached to the benzene ring with 1. O3, 78° C 2. H202 and then my C-H bonds that are sp2 bonded are replaced with OH and I have the double bonded oxygen! Right?

You could take this further. Do you know how to make an anydride from an acid?

[orgopete]

It appears that you know ozonolysys. What are the products of the ozonolysis of diphenylacetylene?