What would be the difference in reactivity if ethyl 3-methylbenzoate was treated in a reduction with...

What would be the difference in reactivity if ethyl 3-methylbenzoate was treated in a reduction with NaBH4 vs LiAlH4? I know that NaBH4 is only powerful enough to reduce ketones and aldehydes, and ethyl 3-methylbenzoate has a ketone group, but I am confused as to how different LAH would be?

Expert Solution

Ethyl 3-methylbenzoate has a ester group, not a ketone group. In LiAlH₄ the hydride source is AlH₄^-, and in NaBH₄ the hydride source is BH₄^-, the hydride source AlH₄^- is a stronger hydride source than BH₄^-.. This is beacuse aluminium is less electronegative than boron, and thus the electron cloud is shifted more towards the hydrogen in AlH₄^- compare to BH₄^-. This is the reason aluminium hydride is a better hydride donor.

Anoter reason is from the comparision of metals (Lithium and sodium). Lithium is more electropositive than sodium and thus is a better lewis acid, and is therefore able to activate the carbonyl more effectively compared to sodium.

The carbonyl carbon of esters have a lone pair which is in resonance with the double bond of carbonyl group. NaBH₄ being a weaker reducing agent cannot reduce any of these. Thus esters are mostly reduced by LiAlH₄ and not by NaBH₄.

The detailed mechanism of the reduction of esters by LiAlH₄ is given below:

I tried my best to meet your expectations. Kindly motivate me with a THUMBS UP.

Thankyou

queen_honey_blossom answered 11 months ago

what is crime reduction, supply reduction and Demand Reduction of the War on Drugs? How would...

what is crime reduction, supply reduction and Demand Reduction of the War on Drugs? How would you apply the Deviance and Rational Analytical models to the supply reduction and crime reduction strategies?

Describe the observed order of arene reactivity. What will be the order of the arene reactivity...

Describe the observed order of arene reactivity. What will be the order of the arene reactivity and how can i know? Arene: Toluene, Acetanilide, Benzhydrol, Anisole, Diphenyl ether. All five arenes were asked to be mixed with 35mL of acetic acid and 0.5mL of a 0.05M bromine solution. what will be the fastest and slowest? what will be the order of reaction and why?

What temperature change would cause a 1.40% increase in the volume of a quantity of Ethyl...

What temperature change would cause a 1.40% increase in the volume of a quantity of Ethyl alcohol that was initially at 17 °C? (The coefficient of volume expansion of Ethyl alcohol is 1.12×10^−3 oC^−1)

in the hydrolysis of ethyl benzoate, describe what reagents you would use to isolate the product...

in the hydrolysis of ethyl benzoate, describe what reagents you would use to isolate the product form the starting material:

What would be the result of using a very polar solvent like methanol (instead of ethyl...

What would be the result of using a very polar solvent like methanol (instead of ethyl acetate) to develop your TLC plates?

3. If the government were to reduce income taxes, how would the reduction affect output and...

3. If the government were to reduce income taxes, how would the reduction affect output and the price level in the short run? In the long run? Describe how the aggregate supply and aggregate demand curves would be affected?

Given the reactivity difference for the 4- position versus the 1-position, do you think that the...

Given the reactivity difference for the 4- position versus the 1-position, do you think that the chlorine atom stabilizes, destabilizes or has no effect on an adjacent radical? Is it the Resonance or Inductive effect? Use: 1,4-dichlorobutane, 1,3-dichlorobutane, 1,2-dichlorobutane and 1,1-dichlorobutane

What would happen to a sexually reproducing organism if there were no reduction in chromosome number...

What would happen to a sexually reproducing organism if there were no reduction in chromosome number during meiotic division? Give an example

1.What is glaucoma and how can it be treated? 2.What happens if it is not treated?...

1.What is glaucoma and how can it be treated? 2.What happens if it is not treated? 3.What is noise-inducing hearing loss? 4. Name people that are higher likely to get this and what is the treatment?

What is the expected aromatic hydrocarbon reactivity of these compounds and why ? (which is the...

What is the expected aromatic hydrocarbon reactivity of these compounds and why ? (which is the fastest and which is the slowest and why?) a bromine solution in acetic acid was added to these compound. Toluene , Acetanilide , Benzhydrol, Anisole, Diphenyl ether

Question