Question

In: Chemistry

Discuss the reduction of acetophenone with sodium borohydride and a workup of ethanol. My % yield...

Discuss the reduction of acetophenone with sodium borohydride and a workup of ethanol. My % yield is 21.5% . Analyze why is this result and relate to the theories and concepts. Please provide a descriptive paragraph, please

Solutions

Expert Solution

In the reaction between acetophenone and sodium borohydride product formed is 1 - Phenylethanol and boron salts.

In this reaction firstly we take sodium borohydride in beaker and then add ethanol. Reaction between acetophenone and sodium borohydride is highly exothermic so it must be carried out in fumehood and the reaction temperature must be maintained by ice bath. After the reaction is completed then the excess borohydride and ethoxyborohydride destroyed by aqeous acid.Ethanol is water soluble so in this reaction organic and inorganic products formed cannot be seperated by simple extraction with water and diethyl ether so lost of product is more. So first work is to boil off much of the ethanol. And then add water and diethyl ether to seperate the organic and inorganic products.

The pecentage yeild = Actual yeild / Theoritical yeild X 100%

Actual yeild is the actual amount produced when the experiment or reaction is carried out.

Theoritical yeild is the amount of product calculated from the limiting reactant.

Percentage yeild is less because of factors like:

1) The reaction may not produce stiochiometric amount of product. This can be possible because of slow rate, equilibrium set up, decomposition of reactant or product or evaporation.

2) During work of solvent extraction or crystallization, product is not completely seperated and it is discarded so there is loss of product occurs, then the percentage yeild is less.

3) Some product may remain inside the reaction, purification vessel.

4) In our case if temperature is not properly maintained then reactant will not completely react and product form is less in yeild.

Beacause of these factors percentage yeild is less.


Related Solutions

I completed a reduction of 4-tert-butylcyclohexanol with sodium borohydride, which was supposed to yield the cis-...
I completed a reduction of 4-tert-butylcyclohexanol with sodium borohydride, which was supposed to yield the cis- and trans- isomers of 4-tert-butylcyclohexanol. I followed every step exactly as the lab manual said, but yielded no product. How do I explain this?? What step in the process could have led to the loss of any product?
Expt 55 Micro: Borohydride Reduction of a Ketone: Hydrobenzoin from Benzil 3. Sodium borohydride can be...
Expt 55 Micro: Borohydride Reduction of a Ketone: Hydrobenzoin from Benzil 3. Sodium borohydride can be used in ethanol solutions to rapidly reduce aldehydes and ketones at room temperature. Even though lithium aluminum hydride (LiAlH4) is much more reactive than sodium borohydride (NaBH4) it can’t be used to reduce aldehydes and ketones in ethanol solutions. Explain why not? NOTE: The answer is not the quote from the lab book “Unlike lithium aluminum hydride, sodium borohydride is insoluble in ether and...
Sodium Borohydride Reduction of a Ketone 1. How will the dibenzalacetone product be isolated from the...
Sodium Borohydride Reduction of a Ketone 1. How will the dibenzalacetone product be isolated from the reaction mixture and how will it then be further purified? How will the product be characterized? 2. What apparatus and conditions (solvent, temp., reaction time, etc) will be used for the reaction? 3. Identify which is the reducing agent and which is the oxidizing agent in the reaction of benzophenone with sodium borohydride and explain your reasoning, ie. show the changes in oxidation states...
In the reduction of benzophenone with NaBH4... After dissolving benzophenone in methanol and adding sodium borohydride,...
In the reduction of benzophenone with NaBH4... After dissolving benzophenone in methanol and adding sodium borohydride, (a). Why do we add ice water to the mixture and then heat it? (b). Why does the addition of water precipitate the product?
why can sodium borohydride be preferred in reduction to alcohols over H2/Pt?
why can sodium borohydride be preferred in reduction to alcohols over H2/Pt?
In the reduction of 4--tert-butylcyclohexanone using sodium borohydride, what are the products? What is the product...
In the reduction of 4--tert-butylcyclohexanone using sodium borohydride, what are the products? What is the product ratio of these products, and explain mechanistically why this product ratio occurs. Finally, how can you use a NMR spectra to determine the product ratio?
Vanillin Reduction with Sodium Borohydride to form Vanillyl Alcohol Started with 2.517g vanillin and 5.0mL NaBH4...
Vanillin Reduction with Sodium Borohydride to form Vanillyl Alcohol Started with 2.517g vanillin and 5.0mL NaBH4 Crude Product= 7.568g Recrystallized Product= 2.297g a) Calculate the %yield for both the crude and "fully" synthesized product b) Explain why this is likely not 100%. How could this be improved c) Draw mechanism
Calculate the theoretical weight of sodium borohydride needed to reduce 50mg of benzoin.
Calculate the theoretical weight of sodium borohydride needed to reduce 50mg of benzoin.
1. (a) The addition of acetic acid to sodium borohydride will cause the displacement of one...
1. (a) The addition of acetic acid to sodium borohydride will cause the displacement of one or more hydrides from each boron atom with an acetate ion. The resulting borohydride reducing agent is less reactive than the parent sodium borohydride. What does tartaric acid do in the sodium borohydride reduction to cause a chiral reaction environment for the ketone reduction reaction? Illustrate with a structure. (b) What are the specific rotations of pure (R)-ethyl 3-hydroxybutanoate, (S)-ethyl 3-hydroxybutanoate and (L)- tartaric...
Hi, I am doing an experiment that is called NaBH4 reduction of acetophenone. I am having...
Hi, I am doing an experiment that is called NaBH4 reduction of acetophenone. I am having trouble understand the techinque/wording when using a sep funnel. These are some of the procedures below: 1. Pour the mixture into a separatory funnel and add 20 mL of ice water. Rinse the beaker with additional ice water (5 mL) and add the rinsing to the separatory funnel. Rinise the beaker with ether (2 X 15 mL), adding the ether to the separatory funnel....
ADVERTISEMENT
ADVERTISEMENT
ADVERTISEMENT