Compound W, C8H17Br, and X, C8H17CI, are products of the radical bromination (W), and chlorination (X), of 2,4-dimethylhexane. W and X are each chiral. W reacts readily in water to form a chiral substitution product Y, C8H₁7OH. Reaction of a single enantiomer of W produces a single enantiomer of Y as the only substitution product. X likewise reacts readily in water though at a slower rate than W; a chiral substitution product Z, C8H₁7OH, is again formed. Unlike W, however, reaction of a single enantiomer of X produces Z that is nearly racemic. Propose structures for W and X. 0 • Do not use stereobonds in your answer. • In cases where there more than one possible structure for each molecule, just give one for each. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu. ChemDoodleⓇ 0 0 • [] 2 0 ChemDoodleⓇ O [F
Compound W, C8H17Br, and X, C8H17CI, are products of the radical bromination (W), and chlorination (X), of 2,4-dimethylhexane. W and X are each chiral. W reacts readily in water to form a chiral substitution product Y, C8H₁7OH. Reaction of a single enantiomer of W produces a single enantiomer of Y as the only substitution product. X likewise reacts readily in water though at a slower rate than W; a chiral substitution product Z, C8H₁7OH, is again formed. Unlike W, however, reaction of a single enantiomer of X produces Z that is nearly racemic. Propose structures for W and X. 0 • Do not use stereobonds in your answer. • In cases where there more than one possible structure for each molecule, just give one for each. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu. ChemDoodleⓇ 0 0 • [] 2 0 ChemDoodleⓇ O [F
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
Chapter2: Alkanes And Cycloalkanes
Section: Chapter Questions
Problem 2.46P
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