Textbook Question
Suggest a reagent and a reactant that could be used to form the following molecules by conjugate addition of a cuprate. There can be multiple possibilities.
(c)
13. Alcohols and Carbonyl Compounds
Organometallic Cumulative Practice
3:42 minutesProblem 27b
Textbook Question
What are the products of the following reactions?
b. 
Verified step by step guidance1
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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3mKey Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Reaction Mechanisms
Understanding reaction mechanisms is crucial in organic chemistry as they describe the step-by-step process by which reactants transform into products. This includes identifying intermediates, transition states, and the movement of electrons. Familiarity with mechanisms helps predict the outcome of reactions and the stability of products formed.
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Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Recognizing functional groups allows chemists to predict reactivity and the types of products that can be formed in a reaction. Common functional groups include alcohols, carboxylic acids, and amines.
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Stereochemistry
Stereochemistry involves the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. It is essential for understanding isomerism, where compounds with the same molecular formula can have different structures and properties. Stereochemical considerations can significantly influence the products of reactions, especially in chiral environments.
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