Concept explainers
(a)
Interpretation:
How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.
Concept introduction:
A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an
(b)
Interpretation:
How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.
Concept introduction:
A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.
(c)
Interpretation:
How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.
Concept introduction:
A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.
(d)
Interpretation:
How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.
Concept introduction:
A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.
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- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning