Chapter 17, Problem 37P

Draw the products formed when pentanal $\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{CHO}\right)$ is treated with each reagent. With some reagents, no reaction occurs.

a. ${\text{NaBH}}_{\text{4}}$, ${\text{CH}}_{\text{3}}\text{OH}$

b. ${\text{LiAlH}}_{\text{4}}$, ${\text{H}}_{\text{2}}\text{O}$

c. ${\text{H}}_2\left(1\text{equiv}\right)$, $\text{Pd}-\text{C}$

d. $\text{PCC}$

e. ${\text{Na}}_{\text{2}}{\text{Cr}}_{\text{2}}{\text{O}}_{\text{7}}$, ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$, ${\text{H}}_{\text{2}}\text{O}$

f. ${\text{Ag}}_{\text{2}}\text{O},{\text{NH}}_{\text{4}}\text{OH}$

g. $\left[\text{1}\right]{\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{MgBr}$, $\left[\text{2}\right]{\text{H}}_{\text{2}}\text{O}$

h. $\left[\text{1}\right]{\text{C}}_6{\text{H}}_5\text{Li}$, $\left[\text{2}\right]{\text{H}}_{\text{2}}\text{O}$

i. $\left[\text{1}\right]\left({\text{CH}}_3\right)\text{CuLi}$, $\left[\text{2}\right]{\text{H}}_{\text{2}}\text{O}$

j. $\text{HC}\equiv \text{CNa}$, $\left[\text{2}\right]{\text{H}}_{\text{2}}\text{O}$

k. ${\text{H}}_{\text{3}}\text{CC}\equiv \text{CLi}$, ${\text{H}}_{\text{2}}\text{O}$

l. The [product in (a), then TBDMS-Cl, imidazole.