Concept: Concept: General Reaction2m
Hey guys! Now we’re going to talk about one of the more important mechanisms in this course. That is mechanism of Fischer Esterification. Fischer Esterification is just another name for acid-catalyzed esterification. When we think about what that is, that would just mean that I’m taking a carboxylic acid and reacting it with alcohol in the presence of acid and I’m getting an ester. I'm getting an ester product hence the term esterification. According to our three rules, this is a totally fine reaction because we said that carboxylic acid and esters have about the same reactivity. It’s pretty easy to switch between the two. According to my three rules, I know this is a favored reaction that this can work. Then why do I have this video? Because it turns out that professors just love to ask about this mechanism because it’s one of the fundamental mechanisms of nucleophilic acyl substitution. That’s why I’m going to go into depth and we're going to draw the whole mechanism for this from scratch. Let's go ahead and do that now.
Concept: Concept: General Mechanism5m
Predict the product. NOTE: the product has 6 oxygens
What is the best choice of reagent(s) to perform the following transformation?
a CH3OH, H2SO4
b CH3I, H2SO4
Draw the organic product(s) for the following reaction. Indicate stereochemistry where appropriate. Assume an aqueous workup, when necessary. A reasonable answer may be “ No Reaction.”
Draw a reasonable mechanism for the reaction below.
Provide a detailed mechanism for the esterification reaction below.
Which of the following is (are) tetrahedral intermediate(s) in the acid catalyzed esterification of benzoic acid with ethanol?
In the acid catalyzed esterification of compound 1, several possible intermediates are shown. Indicate the order in which these intermediates would appear during the conversion of 1 into 2.
a) 1 → I → IV → V→ III → 2
b) 1 → II → IV → 2
c) 1 → III → IV → I→ V → 2
d) 1 → III → I → V→ IV → 2
e) 1 → I → III → IV → 2