Question 15.3: Draw the structure of the aldehyde or ketone formed from the......
Draw the structure of the aldehyde or ketone formed from the oxidation of each of the following alcohols. Assume that reaction conditions are sufficiently mild that any aldehydes produced are not oxidized further.
a.CH_{3}-CH_{2}-CH_{2}-OH b. \begin{matrix} CH_{3}-\underset{|}{C} H-CH_{3} \\ OH\end{matrix}
c. 
d. \begin{matrix} \ \ \ \ \ \underset{|}{C}H_{3} \\ CH_{3}-\underset{|}{C} -OH \\ \ \ \ CH_{3}\end{matrix}
a. This is a primary alcohol that will give the aldehyde propanal as the oxidation product.
\underset{Propanal} {\begin{matrix} \quad\quad\quad\quad \ \ O \\ CH_{3}-CH_{2}-\overset{||}{C}-H \end{matrix}}b. This is a secondary alcohol. Upon oxidation, secondary alcohols are converted to ketones.
\underset{\text{Propanone}}{\begin{matrix} & O & \\ & || & \\ CH_{3}- & C & -CH_{3} \end{matrix}}c. This cyclic alcohol is a secondary alcohol; hence a ketone is the oxidation product.
d. This is a tertiary alcohol. Tertiary alcohols do not undergo oxidation (Section 14.9).