| 
  • If you are citizen of an European Union member nation, you may not use this service unless you are at least 16 years old.

  • You already know Dokkio is an AI-powered assistant to organize & manage your digital files & messages. Very soon, Dokkio will support Outlook as well as One Drive. Check it out today!

View
 

Synthesis of Isopentyl Acetate (Banana Oil)

Page history last edited by Allison 15 years, 11 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)

 

Photo Gallery

 

 

Comments (0)

You don't have permission to comment on this page.