Chapter 20, Problem 39P

Draw the product formed when phenylacetic acid $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{CH}}_{\text{2}}\text{COOH}\right)$ is treated with each reagent. With some no reaction occurs.

a. ${\text{NaHCO}}_{\text{3}}$

b. $\text{NaOH}$

c. ${\text{SOCL}}_{\text{2}}$

d. $\text{NaCl}$

e. ${\text{NH}}_{\text{3}}\text{(1 equiv)}$

f. ${\text{NH}}_{\text{3}}\text{,}△$

g. ${\text{CH}}_{\text{3}}{\text{OH, H}}_{\text{2}}{\text{SO}}_{\text{4}}$

h. ${\text{CH}}_{\text{3}}{\text{OH, OH}}^{-}$

i. ${\text{[1]NaOH; [2]CH}}_{\text{3}}\text{COCl}$

j. ${\text{CH}}_{\text{3}}{\text{NH}}_{\text{2}}\text{, DCC}$

k. ${\text{[1]SOCL}}_{\text{2}}{\text{; [2]CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{NH}}_{\text{2}}\text{(excess)}$

l. ${\text{[1]SOCL}}_{\text{2}}\text{; [2]}{\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{CHOH}$