Textbook Question
Predict the major product when each reagent reacts with ethylene oxide.
(d) PhNH2 (aniline)
(e) KCN (potassium cyanide)
(f) NaN3 (sodium azide)
10. Addition Reactions
Epoxide Reactions
5:35 minutesProblem 45d(vii)
Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (vii) 1. mCPBA 2. H2SO4, H2O
(d) 
Verified step by step guidance1
Step 1: Recognize the reaction type. The problem involves the reaction of an alkene with mCPBA (meta-chloroperoxybenzoic acid), which is a reagent commonly used for epoxidation. This reaction converts an alkene into an epoxide by adding an oxygen atom across the double bond.
Step 2: Analyze the structure of the alkene. Identify the position of the double bond in the alkene molecule. The epoxidation reaction will occur at the double bond, forming a three-membered cyclic ether (epoxide).
Step 3: Consider the stereochemistry. If the alkene is substituted, the stereochemistry of the epoxide will depend on the stereochemistry of the starting alkene. For example, a cis-alkene will produce a cis-epoxide, and a trans-alkene will produce a trans-epoxide.
Step 4: Understand the second step (d). Without additional information about the reagent or conditions in step (d), it is important to note that the epoxide formed in step 1 could undergo further reactions, such as ring-opening, depending on the reagent used. Common reagents for epoxide ring-opening include acids, bases, or nucleophiles.
Step 5: Predict the product(s). Combine the knowledge from steps 1-4 to predict the intermediate epoxide product from mCPBA and then consider how step (d) might modify the epoxide. If step (d) involves a specific reagent, analyze how it interacts with the epoxide to form the final product(s).
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Alkenes
Alkenes are hydrocarbons that contain at least one carbon-carbon double bond (C=C). They are unsaturated compounds and can undergo various reactions, including addition reactions, where atoms or groups are added across the double bond. Understanding the structure and reactivity of alkenes is crucial for predicting the products of their reactions.
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mCPBA (meta-Chloroperbenzoic Acid)
mCPBA is a peracid commonly used in organic chemistry for the epoxidation of alkenes. It introduces an oxygen atom across the double bond, forming an epoxide, which is a three-membered cyclic ether. The use of mCPBA in reactions is significant for synthesizing various organic compounds and understanding the mechanisms of oxidation.
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Epoxidation
Epoxidation is a chemical reaction that converts alkenes into epoxides through the addition of an oxygen atom. This reaction typically occurs under acidic or basic conditions and is important in organic synthesis due to the reactivity of epoxides, which can be further transformed into a variety of functional groups. Recognizing the conditions and reagents that facilitate epoxidation is essential for predicting reaction outcomes.
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