Problem 9: Solvolysis of the following cyclic chloroalkane yield two products corresponding to nucleophilic substitution. Identify the relationship between the predicted substitution products. (Hint: Think about the geometry of the carbocation intermediate and then the direction of nucleophilic attack on the electrophilic carbon. Draw the product or products with appropriate stereochemistry.) OH (solvent) ? The two products are expected to be different conformations of the same compound interconvertible by chair-chair interconversion (also known as chair flip). The substitution products generated in this reaction are diastereomers with two chiral centers in each compound. The substitution products generated in this reaction are constitutional isomers.

Problem 9: Solvolysis of the following cyclic chloroalkane yield two products corresponding to nucleophilic substitution. Identify the relationship between the predicted substitution products. (Hint: Think about the geometry of the carbocation intermediate and then the direction of nucleophilic attack on the electrophilic carbon. Draw the product or products with appropriate stereochemistry.) OH (solvent) ? The two products are expected to be different conformations of the same compound interconvertible by chair-chair interconversion (also known as chair flip). The substitution products generated in this reaction are diastereomers with two chiral centers in each compound. The substitution products generated in this reaction are constitutional isomers.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter30: Orbitals And Organic Chemistry: Pericyclic Reactions

Section30.SE: Something Extra

Problem 14MP: Plastic photochromic sunglasses are based on the following reversible rearrangement of a dye inside...

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