Provide a step-wise solution for the synthesis problem below: Available Reactant HO Synthesis Target OH Hint #1: The correct answer includes one new Chapter 19 reaction and one new Chapter 20 reaction Hint #2: Look out for strategies that lead to "dead ends" due to selectivity of reactions!

Provide a step-wise solution for the synthesis problem below: Available Reactant HO Synthesis Target OH Hint #1: The correct answer includes one new Chapter 19 reaction and one new Chapter 20 reaction Hint #2: Look out for strategies that lead to "dead ends" due to selectivity of reactions!

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

Chapter10: Alcohols

Section: Chapter Questions

Problem 10.50P

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Concept explainers

Reactions at the Alpha Carbon Atom

The position next to the ketone or aldehyde functional group is termed as alpha position and the reaction which occurs at alpha position is called alpha substitution reaction. In an alpha substitution reaction, the alpha proton atom is substituted by an electrophile by the formation of an enol intermediate or enolate ion intermediate. Most of the carbonyl compounds go through an alpha substitution reaction.

Question

Provide a step-wise solution for the synthesis problem below:
Available Reactant
HO
Synthesis Target
.OH
Hint #1: The correct answer includes one new Chapter 19 reaction and one new Chapter 20 reaction
Hint #2: Look out for strategies that lead to "dead ends" due to selectivity of reactions!

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