OCHEM Question

[osimsDDS]

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SO question:

So lets say you have a benzene with a carboxylic acid group, what will happen with these reagents:

1) SOCl2
2) Cl/FeCl3 and Br/FeBr3 or PBr3

Pretty much my question is, when do you know to take off the OH group of the carboxylic acid and replace it with a halide or to add it meta in this case???

When do you know when to do a substitution or to add o,p, or m???

THANKS ALOT ive been trying to figure this out forever...

 

[Thundercatz]

1st one you will replace the OH with the CL and PBr3 will also replace OH.

2nd one you will attach o,p,m style. 2nd one is actually Cl2/FeCl3 and Br2/FeBr3. What happens on the bottom one is one of the Cl/Br groups binds with FeCl3/Br3 leaving the Cl/Br with a positive charge. One of the double bonds in the benzene ring will then act as a nucleophile and attach the positively charge Cl/Br.

 

[DCRedskinsRule]

SO question:

So lets say you have a benzene with a carboxylic acid group, what will happen with these reagents:

1) SOCl2
2) Cl/FeCl3 and Br/FeBr3 or PBr3

Pretty much my question is, when do you know to take off the OH group of the carboxylic acid and replace it with a halide or to add it meta in this case???

When do you know when to do a substitution or to add o,p, or m???

THANKS ALOT ive been trying to figure this out forever...

Do you think you need a super PM for this one? Or do you think the quick explanations will be fine? If you need one, lemme know, but it'll be late tomorrow at the earliest.

 

[osimsDDS]

haha i feel like im good at ochem but when it comes to small stuff i get messed up with these....

So yea i think i need a super super super long PM hahaha...but not too long thanks

 

[osimsDDS]

Do you think you need a super PM for this one? Or do you think the quick explanations will be fine? If you need one, lemme know, but it'll be late tomorrow at the earliest.

haha nvm i got it now thanks anyways DC your the best...SOCl2 and PBr3/PCl5 are strong and take out the OH from the carboxylic acid, the others FeCl3/FeBr3 add o,p,m depending on the substituent on the ring...

correct me if iam wrong, thanks

 

[HoangDDS]

So the #1 substituent will be an acid chloride or acyl cholride and # 3 on the benzene or meta position will be another Cl ?

I have a picture of the cmpd but what is the correct nomenclature?

- 3-chloride,1-benzoyl chloride?

 

[Mstoothlady2012]

I don' think there is any trick to this question. You just have to know your reagents....unless you wanna go in really depth and know all the chemistry and mechanism behind it.