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


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.
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