22. Carboxylic Acid Derivatives: NAS

Using any necessary reagents, show how you would accomplish the following syntheses.

(g)

Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).

(d) hexanoic acid → hexanal

Show how you would use an acid chloride as an intermediate to synthesize

(b) phenyl propionate (CH₃CH₂COOPh) from propionic acid and phenol.

Show how you would accomplish the following syntheses using amides as intermediates. You may use any necessary reagents.

(a) benzoic acid → benzyldimethylamine

(b) pyrrolidine → N-ethylpyrrolidine

(c) cyclopentanecarboxylic acid → cyclopentanecarbonitrile