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Ch. 11 - Organometallic Compounds
Bruice - Organic Chemistry 8th Edition
Bruice8th EditionOrganic ChemistryISBN: 9780135213711Non è quello che usi tu?Cambia libro di testo
Capitolo 11, Problema 27b

What are the products of the following reactions?
b.

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Step 1: Analyze the reactants. The starting material is a diorganocuprate reagent ((C6H5CH2)2CuLi), which is a nucleophile capable of attacking electrophiles such as epoxides.
Step 2: Identify the electrophile. Ethylene oxide is an epoxide, a three-membered ring containing oxygen. It is highly strained and reactive, making it susceptible to nucleophilic attack.
Step 3: Predict the reaction mechanism. The diorganocuprate reagent will attack the less hindered carbon of the ethylene oxide ring, opening the ring and forming a new bond between the benzyl group (C6H5CH2) and the carbon of the epoxide.
Step 4: Consider the second step. After the ring-opening reaction, the intermediate is treated with HCl and H2O. This step protonates the oxygen atom, resulting in the formation of an alcohol group (-OH) at the site of the ring opening.
Step 5: Write the product structure. The final product will have a benzyl group (C6H5CH2) attached to one of the carbons of the former ethylene oxide, and the other carbon will bear a hydroxyl group (-OH).

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