Why does acrylonitrile (A) react faster with 1,3-butadiene in a pericyclic reaction than methyl vinylether (B)? Check all that apply.CENAO 1. The bond lenght between carbon and nitrogen is greater than the bond lenght between carbon and oxygen which brings the bulky cyano group further away from the carbon-carbon double bond. That reduces stericalO 2. The LUMO of acrylonitrile (A) is has a lower energy than the LUMO of methyl vinylether (B) which makes the reaction go fasterO 3. The high electronegativity of the oxygen atom in ether B polarizes the carbon-carbon double bond which reduces the reaction rate.O 4. The boiling point of nitrile A is higher than the boiling point of ether B, therefore the reaction can be carried out at a higher temperature which accelerates the reaction.hindrance and accelerates the reaction.

Answered: Why does acrylonitrile (A) react faster…

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ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Why does acrylonitrile (A) react faster with 1,3-butadiene in a pericyclic reaction than methyl vinylether (B)? Check all that apply.
CEN
A
O 1. The bond lenght between carbon and nitrogen is greater than the bond lenght between carbon and oxygen which brings the bulky cyano group further away from the carbon-carbon double bond. That reduces sterical
O 2. The LUMO of acrylonitrile (A) is has a lower energy than the LUMO of methyl vinylether (B) which makes the reaction go faster
O 3. The high electronegativity of the oxygen atom in ether B polarizes the carbon-carbon double bond which reduces the reaction rate.
O 4. The boiling point of nitrile A is higher than the boiling point of ether B, therefore the reaction can be carried out at a higher temperature which accelerates the reaction.
hindrance and accelerates the reaction.

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Step 1 Background Information

Reaction of 1,3-butadiene with A or B is an diels alder reaction. In diels alder reaction, diene must be electron rich and dienophile must be electron deficient so that rate of reaction reaction will faster. In diels alder reaction, HOMO of diene and LUMO of dienophile combine to give product. If this energy gap is high rate of reaction is slow and if it is low then rate of reaction will be faster. Dienophile which is bonded with electron withdrawing group then it will lowers the energy of LUMO so that energy between HOMO of diene and LUMO of dienophile decreases and rate will be faster.

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