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Synthesis of Isopentyl Acetate (Banana Oil)

Page history last edited by Allison 12 years, 6 months ago

 

2) Changes to published procedure

We used 9 mL of isopentyl alcohol (3-methyl-1-butanol), 12 ml acetic acid, and 3 mL H2SO4.

Reflux was done for 40 min.

The routine liquid-liquid washings were done.

The ester was distilled to its final purified form.

We performed an IR spectrum of the products.

 

3) Positive

+ A classic experiment that covers an important reaction.

+ The product is easy to put between salt plates for the IR.

+ It smells nice.

 

4) Neutral

± It seems like a lot of acid is needed. Isn’t excess acetic acid enough acid?

± During reflux the mixture turns a dark color. Is this because of impurities in the alcohol?

 

5) Negative

- This would be much more interesting if the students could mix-and-match several alcohols and carboxylic acids. Wade P.A.; Rutkowsky S.A.; King D.B. A simple combinatorial experiment based on Fischer esterification - An experiment suitable for the first-semester organic chemistry lab. J Chemical Education 2006, 83(6), 927-928.

 

6) Inquiry & Extension ideas.

● The combinatorial approach is very cool. Any carboxylic acid matched with a primary alcohol should give a decent yield. At a certain point it would be impractical to distill the resulting esters, possibly.

● Acid-catalyzed reactions have the option of changing the acid.

● Acid-catalyzed reactions always have the possibility of interesting side reactions occurring: eliminations, polymerization, etc…

 

Student Comments 2008: Synthesis of Isopentyl Acetate (Banana Oil)

 

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