Chemistry Reference
In-Depth Information
CHAPTER 8 SOLUTIONS
1. Describe the following functional group transformation in mechanistic terms. Show
arrow pushing.
This is an addition-elimination reaction between methanol and a protonated car-
boxylic acid. As illustrated below, hydrochloric acid protonates the carboxylic acid.
Methanol then adds to the protonated carboxylic acid. Elimination of water liberates
the methyl ester.
Please note that this reaction is generally run with methanol as the solvent. Under
these circumstances, the reverse reaction, ester hydrolysis, does not proceed
because the water being liberated during the reaction is so dilute in the methanol
that water molecules never interact with the forming ester.
This is a hydrolysis reaction where a hydroxide anion adds to a nitrile. As
illustrated below, the hydroxide anion adds to the nitrile carbon atom. Proton
