Chapter 18.8, Problem DQ

The following sequence of steps is used to create the carboxylic acids that can be used as the first reactant, where X can be a wide variety of groups. Answer true or false about each of the following statements.

1. 1. Step 1 would best be performed at a pH below the pK_a of ammonium.
2. 2. Step 1 would create an imine that undergoes nucleophilic attack by cyanide in Step 2.
3. 3. The hydrolysis of the nitrile created in Step 2 would be better performed in base rather than the acid shown.
4. 4. Step 4 is a resolution of a racemic mixture that results from Steps 1–3 and does not require a chiral reagent.