Which of the following starting materials and reagents would be best to produce a racemic mixture of 3-methyl-3-hexanol? heptanone and 1. CH3MgBr 2. H3O+ hexanal and 1. CH3MgBr, 2. H3O+ 3-hexanone and 1. CH3MgBr, 2. H3O+ butanal and 1. CH3CH2MgBr, 2. H3O+

Which of the following starting materials and reagents would be best to produce a racemic mixture of 3-methyl-3-hexanol? heptanone and 1. CH3MgBr 2. H3O+ hexanal and 1. CH3MgBr, 2. H3O+ 3-hexanone and 1. CH3MgBr, 2. H3O+ butanal and 1. CH3CH2MgBr, 2. H3O+

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

Chapter24: Catalytic Carbon-carbon Bond Formation

Section: Chapter Questions

Problem 24.9P

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Question

Which of the following starting materials and reagents would be best to produce a racemic mixture of 3-methyl-3-hexanol?

heptanone and 1. CH₃MgBr 2. H₃O⁺

hexanal and 1. CH₃MgBr, 2. H₃O⁺

3-hexanone and 1. CH₃MgBr, 2. H₃O⁺

butanal and 1. CH₃CH₂MgBr, 2. H₃O⁺

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