Macmillan Learning Organocuprates are organometallic reagents with the general formula R, CuLi. Predict the organic coupling product in the organocuprate reaction shown. Draw the product.
Macmillan Learning Organocuprates are organometallic reagents with the general formula R, CuLi. Predict the organic coupling product in the organocuprate reaction shown. Draw the product.
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Transcribed Image Text:### Organocuprate Chemistry: Predicting Coupling Products
**Introduction:**
Organocuprates are organometallic reagents with the general formula R₂CuLi. They are used in organic chemistry for carbon-carbon bond formation through coupling reactions.
**Reaction Overview:**
**Reagents:**
- **R₂CuLi (Organocuprate):** This is shown as a compound with a copper (Cu) center bonded to two alkenyl groups and a lithium cation (Li⁺).
- **An Alkyl Halide (1-Bromohexane):** The molecule includes a hexane chain with a terminating bromine (Br) atom.
**Reaction:**
- The organocuprate reacts with the alkyl halide in a coupling reaction, resulting in the formation of a new carbon-carbon bond.
**Task:**
Predict the organic coupling product in the reaction shown.
**Diagram Explanation:**
- The left side of the reaction illustrates the reactants: the organocuprate (with two vinyl groups) and the alkyl halide (1-bromohexane).
- An arrow indicates the transformation into the product.
- To the right, a skeletal structure showing the anticipated coupling product is depicted. This product should incorporate the two vinyl groups from the organocuprate and the alkyl chain originally attached to the bromine atom.
**Conclusion:**
Through this reaction, a new C-C bond is formed between one of the alkenyl groups from the organocuprate and the alkyl group from the halide, effectively extending the carbon skeleton and creating a longer carbon chain. Understanding these reactions is essential for mastering organic synthesis techniques.
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