2. Our knowledge of chair conformations allows us to use them to determine a great deal abouta reaction's mechanism. In particular, using a t-butyl group to 'fix' a cyclohexane in a singleconformation can help us learn about the spatial requirements and energetics of a reaction.Consider the following two reaction products:a.NO NIDALOH1) NaCN2) H+1) NaBH42) H3O+OHGroup-H-CN-OHA Value (kcal/mol)Defined as 00.2 kcal/mol1.0 kcal/molDraw the most stable chair conformation for each of the two products.b. Based on the A values in the table above, do the two products have the most stableconformation at the new stereocenter?

Repulsive interaction between an axial substituent located on carbon atom 1 of a cyclohexane ring…

2. Our knowledge of chair conformations allows us to use them to determine a great deal about a reaction's mechanism. In particular, using a t-butyl group to 'fix' a cyclohexane in a single conformation can help us learn about the spatial requirements and energetics of a reaction. Consider the following two reaction products: 1) NaCN CN 2) H* OH 1) NaBH4 2) H3O+ OH Group -H -CN -OH A Value (kcal/mol) Defined as 0 0.2 kcal/mol 1.0 kcal/mol a. Draw the most stable chair conformation for each of the two products. b. Based on the A values in the table above, do the two products have the most stable conformation at the new stereocenter?

2. Our knowledge of chair conformations allows us to use them to determine a great deal about a reaction's mechanism. In particular, using a t-butyl group to 'fix' a cyclohexane in a single conformation can help us learn about the spatial requirements and energetics of a reaction. Consider the following two reaction products: 1) NaCN CN 2) H* OH 1) NaBH4 2) H3O+ OH Group -H -CN -OH A Value (kcal/mol) Defined as 0 0.2 kcal/mol 1.0 kcal/mol a. Draw the most stable chair conformation for each of the two products. b. Based on the A values in the table above, do the two products have the most stable conformation at the new stereocenter?

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter14: Elimination

Section: Chapter Questions

Problem 46CTQ

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2. Our knowledge of chair conformations allows us to use them to determine a great deal about a reaction's mechanism. In particular, using a t-butyl group to 'fix' a cyclohexane in a single conformation can help us learn about the spatial requirements and energetics of a reaction. Consider the following two reaction products: CN 1) NaCN 2) H+ OH 1) NaBH4 2) H3O+ OH Group -H -CN A Value (kcal/mol) Defined as 0 0.2 kcal/mol -OH 1.0 kcal/mol c. For any products that do have the most stable conformation, does our understanding of the mechanism allow for ‘thermodynamic control'? d. If one of the products is not the most stable, can you explain the observed product based on ‘kinetic control'? (Does the most easily formed transition state result in the observed product?) Consider the chair-like conformation of the starting material.
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