Fischer esterification

Problem # 729

The ester below was dissolved in a solution of water, a small amount of which was isotopically labeled with O-18, denoted with an asterisk.

After a few hours, some isotopically labeled oxygen was found in the ester. Where was it found in the ester? Can you explain why?

Problem # 727

Show how the ester below can be prepared from propene.

Problem # 725

A chemist carried out a Fischer esterification using methanol that was isotopically labeled with 18O (indicated with an asterisk).

Which one of the esters below (A-D) was formed?

Problem # 724

Use curved arrows to show the formation of the tetrahedral intermediate of a Fischer esterification reaction (shown below). There are three steps in total.

Problem # 708

The overall mechanism for Fischer esterification is shown below. This isn't a real mechanism, just an outline.

Methanol (the nucleophile) attacks the carbonyl carbon, forming a tetrahedral intermediate, which then loses a water to reform the carbonyl. This mechanism is called nucleophilic acyl substitution.


Use curved arrows to draw a full mechanism for this reaction. I've included structures for you to use as a guide.

This reaction takes place under acidic conditions, so the mechanism you draw will be similar to those in problem 706.

Problem # 679

Compound A (C5H12O) is oxidized using aqueous chromium (Jones reagent) to compound B (C5H10O2), which is then treated with methanol under acidic conditions to yield compound C (C6H12O2) and water.

The 1H NMR of compound C is shown below. Determine the structures of compounds A, B, and C.