The flavor and odor of fruits comes primarily from the esters they contain. For example, a major component in the flavor of oranges is octyl acetate. Draw the organic products formed when octyl acetate reacts with aqueous sodium hydroxide.

Explanation:

Concepts and reason

This problem is based on the concept of hydrolysis of esters.

An ester is hydrolyzed to a carboxylic acid and an alcohol when treated with aqueous acid or aqueous base. Under alkaline conditions, the carboxylic acid is obtained in the form as its salt.

Fundamentals

Alkaline hydrolysis of ester is done with strong base {\\rm{NaOH}}NaOHand {\\rm{O}}{{\\rm{H}}^ - }OH\u2212acts as nucleophilic reagent. This reaction is reversible, since carboxylate anion has tendency to react with an alcohol and gives back ester.

Step-by-step

Step 1 of 2

Attack of [{ m{O}}{{ m{H}}^ - }]on carbonyl take place as follows resulting formation of tetrahedral intermediate:

\u043e\u043d\u043e\u043d

Explanation | Hint for next step

The {\\rm{O}}{{\\rm{H}}^ - }OH\u2212nucleophile attacks on the electrophilic carbon of an ester {\\rm{C}} = {\\rm{O}}C=O and forms tetrahedral intermediate after breaking the \\pi\u03c0-bond.

Step 2 of 2

Hydrolysis of product formed from step 1 followed by reaction with {\\rm{NaOH}}NaOHis as follows:

The products of the reaction are:

Explanation | Common mistakes

On the reaction of octyl acetate with aqueous sodium hydroxide, the products octyl alcohol and acetate ion are formed after omitting the {\\rm{N}}{{\\rm{a}}^ + }Na+ions.

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