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Ch.10 - Structure and Synthesis of Alcohols
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Non è quello che usi tu?Cambia libro di testo
Capitolo 10, Problema 12c,d

Predict the products of the following reactions.
(c)
(d)

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Step 1: Analyze the first reaction. The reaction involves 1-bromo-4-fluorocyclohexane reacting with magnesium (Mg) in tetrahydrofuran (THF). This is a typical Grignard reagent formation reaction. The magnesium inserts itself into the carbon-bromine bond, forming a Grignard reagent.
Step 2: Write the product of the first reaction. The Grignard reagent formed will be 1-(fluorocyclohexyl)magnesium bromide. The fluorine atom remains intact as it is not reactive under these conditions.
Step 3: Analyze the second reaction. The reaction involves 3-chloro-1-butene (CH₂=CH-CH₂CH₃) reacting with 2 equivalents of lithium (Li) in ether. This is a typical organolithium formation reaction. Lithium replaces the chlorine atom, forming an organolithium compound.
Step 4: Write the product of the second reaction. The product will be 3-lithio-1-butene (CH₂=CH-CH₂CH₂Li). The double bond remains intact as lithium selectively reacts with the chlorine atom.
Step 5: Summarize the reaction types. The first reaction is a Grignard reagent formation, and the second reaction is an organolithium formation. Both reactions involve the replacement of halogens with metal atoms to form reactive organometallic intermediates.

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