Textbook Question
What products are obtained from the reaction of cyclohexene oxide with
a. methoxide ion?
10. Addition Reactions
Epoxide Reactions
5:21 minutesProblem 30b
Textbook Question
What products are obtained from the reaction of cyclohexene oxide with
b. methylamine?
Verified step by step guidance1
Identify the functional group in cyclohexene oxide: Cyclohexene oxide is an epoxide, which is a three-membered cyclic ether. Epoxides are highly reactive due to ring strain and can undergo nucleophilic ring-opening reactions.
Understand the reactivity of methylamine: Methylamine (CH₃NH₂) is a nucleophile due to the lone pair of electrons on the nitrogen atom. It can attack the electrophilic carbon atoms of the epoxide ring.
Determine the site of nucleophilic attack: In an epoxide, the nucleophile typically attacks the less sterically hindered carbon atom of the ring. This is because the transition state is more stable when the nucleophile approaches the less hindered carbon.
Predict the ring-opening mechanism: The nucleophilic attack by methylamine will open the epoxide ring. The nitrogen atom of methylamine will form a bond with the less hindered carbon, while the oxygen atom from the epoxide will remain bonded to the other carbon, forming an alcohol group.
Draw the final product: The product will be a compound where the epoxide ring has been opened, resulting in a 1-amino-2-alcohol structure. Specifically, the methyl group from methylamine will be attached to the nitrogen atom, and the hydroxyl group (OH) will be attached to the other carbon from the original epoxide ring.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Epoxide Chemistry
Epoxides, or oxiranes, are three-membered cyclic ethers that are highly reactive due to the strain in their ring structure. They can undergo various nucleophilic ring-opening reactions, where a nucleophile attacks the less hindered carbon atom of the epoxide, leading to the formation of alcohols or other functional groups. Understanding the reactivity of epoxides is crucial for predicting the products of their reactions with nucleophiles like methylamine.
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Nucleophilic Substitution
Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile replaces a leaving group in a molecule. In the case of cyclohexene oxide reacting with methylamine, the amine acts as a nucleophile, attacking the epoxide and leading to the formation of an amine product. Recognizing the nature of the nucleophile and the substrate is essential for determining the outcome of the reaction.
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Amine Reactivity
Amines are organic compounds derived from ammonia, where one or more hydrogen atoms are replaced by alkyl or aryl groups. They can act as nucleophiles due to the lone pair of electrons on the nitrogen atom, allowing them to participate in various reactions, including the ring-opening of epoxides. The reactivity of methylamine, a primary amine, is particularly relevant in this context as it can lead to the formation of a substituted alcohol or amine product.
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