(c) Treatment of 4-tert-butylcyclohexanone with the unusual reducing agent magnesium hydride leads to the cyclohexanols 1 and 2 as shown below. Answer ALL parts (i) to (iii). HO. 1. MgH₂, THF 2. HCI, H₂O + HO 2 minor product major product (i) Draw the lowest energy chair conformation of each of alcohols 1 and 2. (ii) Hence, explain which of the two compounds is lower in energy. (iii) As shown, isomer 2 is the major product. Explain how this result allows you to decide whether the reaction is under kinetic or thermodynamic control.

(c) Treatment of 4-tert-butylcyclohexanone with the unusual reducing agent magnesium hydride leads to the cyclohexanols 1 and 2 as shown below. Answer ALL parts (i) to (iii). HO. 1. MgH₂, THF 2. HCI, H₂O + HO 2 minor product major product (i) Draw the lowest energy chair conformation of each of alcohols 1 and 2. (ii) Hence, explain which of the two compounds is lower in energy. (iii) As shown, isomer 2 is the major product. Explain how this result allows you to decide whether the reaction is under kinetic or thermodynamic control.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions

Section20.6: Sigmatropic Shifts

Problem 20.12P

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