Final answer:
Acid chlorides can be converted to alcohols using water and a base, while esters require acid or base-catalyzed hydrolysis followed by reduction. Aldehydes are formed by mild oxidation of primary alcohols using PCC or Swern oxidation.
Step-by-step explanation:
To convert acid chlorides to alcohols, a good nucleophile such as water is often used in the presence of a base to neutralize the HCl by-product. The reaction is a simple nucleophilic acyl substitution. In the case of esters, the transformation to alcohols is typically achieved by hydrolysis. Acid-catalyzed hydrolysis involves adding an acid and water, which will convert the ester to the corresponding carboxylic acid and alcohol. However, by using alkaline hydrolysis (saponification), usually with a strong base like NaOH or KOH, and then acidifying the resulting salt, the carboxylic acid can then be reduced to an alcohol using reducing agents like LiAlH4 or BH3.
The formation of aldehydes, or RCHO, can be achieved through the oxidation of alcohols. Primary alcohols can be oxidized using PCC (Pyridinium chlorochromate) or Swern oxidation to form aldehydes without further oxidation to carboxylic acids.