[prncess23]

Is this right?

[sjb]

Consider the valences of carbon and oxygen. You're almost there

[sanderol]

A reaction with SOCl2 is not a fischer esterfication, it's also not any esterfication.

Hint: you do this, before you do the esterfication reaction to make your carboxylic acid more reactive towards nucleophiles....helps?

[Dolphinsiu]

Yes. It is esterification as given by molecular formula C8H6O2.

Your answer is correct since SOCl2 is used to convert carboxyl group COOH into CO2SOCl. With elimination of HCl, SO2, ester is formed. The only wrong thing in the given figure is that the sigma bond between C atom in CH2 and O atom is missing.

[sanderol]

Yes. It is esterification

wrong, the reaction of a carboxyl acid with thionyl chloride is not an esterfication, since you do not generate an ester but an acyl chloride

as given by molecular formula C8H6O2

Since when can we tell reactions by there molecular formula?

Your answer is correct since SOCl2 is used to convert carboxyl group COOH into CO2SOCl.

Wrong your carboxyl acid will by converted to acyl chloride R-COCl.

With elimination of HCl, SO2, ester is formed

HCl and SO2 are indeed eliminated, but this will not yield an ester. There could be an ester generated since there is an secondary alcohol present in your molecule and that one can react with the generated acyl chloride.
A secondary alcohol is less reactive so that is why you need to generate an acyl chloride in order for this reaction to occur.

But still its not called a fischer esterfication, since you would then make an ester from a R-COOH and R-OH. Which in this case doesn't happen.

[ARGOS++]

Dear sanderol;

Yes!, - You are right, except a small detail: It is a primary alcohol not a secondary.

Good Luck!
                    ARGOS⁺⁺

[sanderol]

my bad your right

[prncess23]

thanks you guys.

so what is this if it is not an esterification? this question in in the carboxylic and derivatives chapter. the lab we are doing is synthesis of isoamyl acetate (banana oil)...

[prncess23]

okay...so i did it again...step by step using http://usm.maine.edu/~newton/Chy251_253/Lectures/CarboxylicAcids/Figure6.GIF and this is what i got...(attached below).

The thing that is bothering me is that the product must have the molecular formula of C8H6O2...which is the product that i got in the begining...but...i am being told it is wrong....

[sjb]

That's fine, possibly the first isolable intermediate. Now, you have an acid chloride and an alcohol (forget temporarily that they're in the same molecule). How would they react if you had, for instance benzoyl chloride and benzyl alcohol?

[sanderol]

your product is fine. But this does not yield the molecular formula which you give as an anwser. So another reaction takes place, which I said in my previous post. (part of secondary alcohol is not relevant)

That reaction can happen intermolecular, but this again will not give the right anwser. Can you think of something else what can happen in the context of esterfication?

[Dolphinsiu]

Here is about fischer esterification
http://www.chemhelper.com/fischester.html