3. Answer the following questions involving the SNAC mechanism. a. Draw the arrow-pushing mechanism for the reaction shown below. (Hints: No good nucleophiles are present. Activate the electrophile in the first step. No O leaving groups!) H2SO4 MeOH H20 OH b. Reconsider the mechanism that you drew in the part a. What was the HOMO in the SNAC mechanism? What was the LUMO? НОМО: LUMO: c. Complete the synthesis (aka. series of reactions) that transforms the alkane into a secondary alcohol by filling in the boxes with the missing reagents for each reaction and the missing intermediate product. Br OH Reaction 1 Reaction 2 Reaction 3

3. Answer the following questions involving the SNAC mechanism. a. Draw the arrow-pushing mechanism for the reaction shown below. (Hints: No good nucleophiles are present. Activate the electrophile in the first step. No O leaving groups!) H2SO4 MeOH H20 OH b. Reconsider the mechanism that you drew in the part a. What was the HOMO in the SNAC mechanism? What was the LUMO? НОМО: LUMO: c. Complete the synthesis (aka. series of reactions) that transforms the alkane into a secondary alcohol by filling in the boxes with the missing reagents for each reaction and the missing intermediate product. Br OH Reaction 1 Reaction 2 Reaction 3

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter14: Elimination

Section: Chapter Questions

Problem 31CTQ

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