Sythesis of isopentyl acetate report questions

  • Thread starter Thread starter osumc2014
  • Start date Start date
  • Tags Tags
    Report
Click For Summary
SUMMARY

The discussion focuses on the Fischer esterification process of isopentyl alcohol and acetic acid to produce isopentyl acetate, commonly known as banana oil. Key issues addressed include determining the presence of residual alcohols, factors contributing to low yield (38.13%), and strategies for yield improvement. Participants highlight the importance of distillation, the role of sodium bicarbonate in neutralizing acidity, and the potential benefits of using a Dean-Stark apparatus to sequester products during the reaction.

PREREQUISITES
  • Understanding of Fischer esterification
  • Knowledge of distillation techniques
  • Familiarity with sodium bicarbonate's role in organic reactions
  • Experience with yield optimization strategies in organic synthesis
NEXT STEPS
  • Research the principles of Fischer esterification and its mechanisms
  • Learn about the use of Dean-Stark apparatus for azeotropic distillation
  • Investigate methods to improve yield in esterification reactions
  • Study the effects of reaction conditions such as temperature and catalyst concentration on ester yields
USEFUL FOR

Chemistry students, organic chemists, and laboratory technicians involved in ester synthesis and optimization of reaction yields.

osumc2014
Messages
1
Reaction score
0
Couple questions about the fischer esterification of isopentyl alcohol + acetic acid -----> (acid catalyzed) to form isopentyl acetate or banana oil. Refluxed, used sodium bicarb and na2So4, distilled.
1) how do I know that the final solution did not contain any alcohols?

2)What could have caused a low yield?

3)How to improve the yield? Iknow something w Le chatelier's but anything else?

Thanks!
 
Physics news on Phys.org
The hint is in the use of Na2SO4

Sorry: I Mean its in the use of distillation

(Even though getting a completely pure substance from one distillation is unlikely..)
 
Last edited:
1) NO, the hint is in the use of bicarbonate.
2) time, temperature, catalyst, water in reagents, sloppy work, larger glassware than necessary, warm condenser in the distillation, too much Na2SO4, bad Na2SO4, not enough time over the Na2SO4, bad extraction technique (emulsion), it just goes on and ON!
3) Improve the yield by sequestering one of the products as it is formed. (Dean-Stark?)
 
Whoops, this is what I get for late posting ^^

But why does the use of bicarb have its effects? Surely its just to reduce the acidity after the acid catalysed esterification takes place?
 
Last edited:
The first step of the workup is to extract with water or bicarb. Probably water first followed by a bicarb wash to scavenge the acid. Water is the key of course since the alcohol is isopropyl (water-soluble).

Edit: Whoops! Strike that! Isopentyl alcohol not isopropyl. And isopentyl alcohol is not very water soluble. AbedeuS is right about the distillation being important.
 
Last edited:
what purpose does refluxing serve ?please help.
 
yield was 38.13% and the final ester was 6.87g s opposed to 18.01g.. problems like wat could have caused this?
 

Similar threads

Synthesis of Isopentyl Acetate question
  • · Replies 7 ·
Replies
7
Views
36K