Fischer Esterification

[prncess23]

Is this right?

[chrisf]

I don't actually think this is a Fischer Esterification problem. Thionyl chloride will react with the carboxylic acid functional group to make an acid chloride. It'll react with a primary alcohol via substitution to put in a Cl.

Fischer Esterifications usually use primary alcohols and an acid.

Attached is what I'd predict as the product.

[chrisf]

Here's the Fischer Esterification mechanism, if you have trouble with it.

[prncess23]

I don't actually think this is a Fischer Esterification problem. Thionyl chloride will react with the carboxylic acid functional group to make an acid chloride. It'll react with a primary alcohol via substitution to put in a Cl.

Fischer Esterifications usually use primary alcohols and an acid.

Attached is what I'd predict as the product.

thank you for your reply but that answer is wrong. The molecular formula of the answer is C8H6O2. your answer doesn't fit that formula.

[chrisf]

thank you for your reply but that answer is wrong. The molecular formula of the answer is C8H6O2. your answer doesn't fit that formula.

Where'd you get the answer from? I've never seen thionyl chloride react in that way... Try working out your reaction via mechanism. I disagree with the answer you were given.

I'm pretty sure, still, this isn't Fischer Esterification.

[prncess23]

thank you for your reply but that answer is wrong. The molecular formula of the answer is C8H6O2. your answer doesn't fit that formula.

Where'd you get the answer from? I've never seen thionyl chloride react in that way... Try working out your reaction via mechanism. I disagree with the answer you were given.

I'm pretty sure, still, this isn't Fischer Esterification.

the molecular formula (which is what i think you are reffering to) was given to me in the lab manual.

The exact question as presented in the lab manual is as follows:

Give the structure of the product in the reaction below:

[chrisf]

Apparently it's possible given the carboxylic acid when reacted with thionyl chloride and an alcohol - but thionyl chloride alone?

Thionyl chloride alone will result in the product I gave. If your professor/lab manual tells different, I'd love to see the mechanism for the reaction.

Thionyl Chloride + Carboxylic Acid = Acid Chloride
Thionyl Chloride + Primary Alcohol = Primary Halogenated Alkyl

[prncess23]

yea. it just says thionyl chloride + heat. nothing else.

[chrisf]

yea. it just says thionyl chloride + heat. nothing else.

Interesting - keep me updated! If this works, I'd love to see how.