How to Leverage Nucleophilic Addition Reactions – Part 2

A nucleophilic addition (AN) reaction is an addition reaction where an organic compound with an electrophilic double/triple bond reacts with a nucleophile s.t. the double/triple bond undergoes a cleavage.


It’s often followed by an elimination of a (good) leaving group.

Let’s recall that nucleophilicity and basicity are not the same thing!

Fischer esterification or Fischer–Speier esterification is an esterification reaction by refluxing a carboxylic acid and an alcohol in the presence of an acid catalyst. Most carboxylic acids are suitable for the reaction, but the alcohol should generally be primary/secondary as tertiary alcohols are prone to elimination. Fischer esterification is typically an acid-catalyzed nucleophilic acyl substitution and stereoretentive.

Question:

Predict the major product(s) of the following reaction:



Click/tap to enlarge the image

Solution infographic:



Click/tap to enlarge the image

What other mechanisms do inspire you❓ Let Chemaficionado know in the comments below or at mychemistryhomework@gmail.com❗

NOTE: Post updated since published

References:

(1)    Nucleophilic addition. Wikipedia. https://en.wikipedia.org/wiki/Nucleophilic_addition.

Wikipedia Contributors. Fischer–Speier esterification. Wikipedia.

(2)    Wikipedia Contributors. Fischer–Speier esterification. Wikipedia. https://en.wikipedia.org/wiki/Fischer%E2%80%93Speier_esterification.

‌(3)    Chouhan, M. S. Advanced Problems in Organic Chemistry for JEE, 11th Ed.

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