Organic Chemistry 9th Edition

Published by Brooks Cole
ISBN 10: 1305080483
ISBN 13: 978-1-30508-048-5

Chapter 20 - Carboxylic Acids and Nitriles - Exercises - Page 678b: 21

Answer

See below.

Work Step by Step

Step 1: The three alkyl bromides in this problem first react with magnesium to form the Grignard reagent. In the Grignard reagent, C atom in the C-Mg bond has a higher electronegativity than Mg, so C atom eventually pulls the electron density towards it. In this way, a carbanion where the negative charge falls on the C atom (R:-), and the cation MgX+ are formed. Step 2: In a nucleophilic addition reaction, the negative charge from the carbanion (R:-) is donated to the carbon of carbon dioxide (O=C=O) and the electron density from C=O bond is pulled towards the O atom. As a result, a carboxylate anion (RCOO-) is formed. Step 3: Finally, RCOO- picks up the H+ from the acid added, forming a carboxylic acid RCOOH.
Update this answer!

You can help us out by revising, improving and updating this answer.

Update this answer

After you claim an answer you’ll have 24 hours to send in a draft. An editor will review the submission and either publish your submission or provide feedback.