Sythesis of isopentyl acetate report questions

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In summary, during the fischer esterification of isopentyl alcohol and acetic acid using acid catalysis, the final solution can be ensured to be free of alcohols by first extracting with water or sodium bicarbonate. A low yield can be caused by various factors such as time, temperature, catalyst, water in reagents, sloppy work, and the use of too much or bad sodium sulfate during the distillation process. To improve the yield, one can use techniques such as sequestering one of the products as it is formed. Refluxing serves the purpose of allowing the reaction to reach equilibrium and produce a higher yield. In this particular conversation, the yield was 38.13% and the final ester was
  • #1
osumc2014
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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!
 
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  • #2
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..)
 
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  • #3
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?)
 
  • #4
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?
 
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  • #5
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.
 
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  • #6
what purpose does refluxing serve ?please help.
 
  • #7
yield was 38.13% and the final ester was 6.87g s opposed to 18.01g.. problems like wat could have caused this?
 

1. What is isopentyl acetate?

Isopentyl acetate is an organic compound with the chemical formula C7H14O2. It is commonly known as banana oil due to its distinct fruity odor. It is used as a flavoring agent in food products and as a solvent in various industrial applications.

2. What is the purpose of synthesizing isopentyl acetate?

The purpose of synthesizing isopentyl acetate is to produce a pure and concentrated form of the compound for various industrial and commercial uses. It can also be used in laboratory experiments to study the properties and reactions of organic compounds.

3. How is isopentyl acetate synthesized?

Isopentyl acetate can be synthesized through an esterification reaction between isopentyl alcohol and acetic acid, using a catalyst such as concentrated sulfuric acid. This reaction produces isopentyl acetate and water as by-products.

4. What are the potential hazards of working with isopentyl acetate?

Isopentyl acetate is flammable and can form explosive mixtures with air. It can also cause irritation to the eyes, skin, and respiratory tract upon exposure. Proper safety precautions, such as wearing protective equipment and working in a well-ventilated area, should be taken when handling this compound.

5. How is the purity of synthesized isopentyl acetate determined?

The purity of synthesized isopentyl acetate can be determined through various analytical techniques, such as gas chromatography or nuclear magnetic resonance spectroscopy. These methods can identify and quantify the different components present in the compound, ensuring its purity and quality.

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