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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Chapter 19 Solutions
ORGANIC CHEMISTRY SMARTWORK5 - ACCESS
- Draw the MAJOR product and a detailed mechanism for the following reaction. Specify stereochemistry where appropriate.arrow_forwardFor each of the following reactions draw the structure of the major organic product in the box provided.Each numbered set of reagents above or below the arrow represents a complete separate reaction.For multi-step reactions give only the structure of the final product.arrow_forwardDraw the complete, detailed mechanism for the reaction shown here, and explain why nucleophilic attack takes place predominantly at the epoxide carbon that is attached to the vinyl group. HCI H,0 ОН 63%arrow_forward
- The attached reaction does not afford the major product that is given.Explain why this is so, and draw the structure of the major productactually formed.arrow_forwardDraw the major organic product for each of the following reactions. You must show the correct stereochemistry of the product where relevant.arrow_forwardThe reaction shown here proceeds via a carbocation rearrangement. Draw a complete, detailed mechanism to account for the product. Explain why the carbocation rearrangement is favorable. CH;OH Brarrow_forward
- Draw the major substitution and elimination products for the reaction shown below. You must show the correct stereochemistry where applicable.arrow_forwardThe attached reaction does not afford the major product that is given.Explain why this is so, and draw the structure of the major product actually formed.arrow_forward
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- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
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