Chapter 12, Problem 35P

Draw the organic products formed when cyclopentene is treated with each reagent. With some

reagents, no reaction occurs.

a. ${\text{H}}_{\text{2}}+\text{Pd-C}$

b. ${\text{H}}_{\text{2}}+$ Lindlar catalyst.

c. $\text{Na},{\text{NH}}_{\text{3}}$.

d. ${\text{CH}}_{\text{3}}{\text{CO}}_{\text{3}}\text{H}$

e. $\left[1\right]$ ${\text{CH}}_{\text{3}}{\text{CO}}_{\text{3}}\text{H}$; $\left[2\right]$ ${\text{H}}_{\text{2}}\text{O},{\text{HO}}^{-}$

f. $\left[1\right]$ ${\text{OsO}}_{\text{4}}+\text{NMO}$ $\left[2\right]$ ${\text{NaHSO}}_{\text{3}}+{\text{H}}_{\text{2}}\text{O}$

g. ${\text{KMnO}}_{\text{4}}$, ${\text{H}}_{\text{2}}\text{O},{\text{OH}}^{-}$

h. $\left[1\right]{\text{LiAlH}}_{\text{4}}\text{;}\left[2\right]{\text{H}}_{\text{2}}\text{O}$.

i. $\left[1\right]{\text{O}}_3\text{;}\left[2\right]{\text{CH}}_{\text{3}}{\text{SCH}}_{\text{3}}$

j. ${\left({\text{CH}}_{\text{3}}\right)}_{\text{3}}\text{COOH}$, $\text{Ti}{\left[\text{OCH}{\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\right]}_{\text{4}}$, $(-)\text{-DET}$

k. $\text{mCPBA}$

l. Product in (k); $\left[1\right]$ ${\text{LiAlH}}_{\text{4}}$; $\left[2\right]$ ${\text{H}}_{\text{2}}\text{O}$