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Ch.13 Alkenes, Alkynes, and Aromatic Compounds
McMurry - Fundamentals of GOB 8th Edition
McMurry8th EditionFundamentals of GOBISBN: 9780134015187Not the one you use?Change textbook
Chapter 13, Problem 42

When ethylbenzene is reacted with nitric acid, three possible benzenes containing both a nitro group and an ethyl group are obtained. Draw and name them.

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Step 1: Understand the reaction. Ethylbenzene reacts with nitric acid in the presence of sulfuric acid, undergoing an electrophilic aromatic substitution reaction. This introduces a nitro group (-NO₂) onto the benzene ring.
Step 2: Identify the positions on the benzene ring where substitution can occur. The ethyl group (-CH₂CH₃) is an electron-donating group, which directs the incoming nitro group to the ortho and para positions relative to itself.
Step 3: Draw the three possible products. These are: (1) ortho-nitroethylbenzene, where the nitro group is adjacent to the ethyl group, (2) meta-nitroethylbenzene, where the nitro group is one position away from the ethyl group, and (3) para-nitroethylbenzene, where the nitro group is opposite the ethyl group on the benzene ring.
Step 4: Name the compounds systematically. Use IUPAC nomenclature: (1) 1-ethyl-2-nitrobenzene for the ortho product, (2) 1-ethyl-3-nitrobenzene for the meta product, and (3) 1-ethyl-4-nitrobenzene for the para product.
Step 5: Verify the stability and likelihood of formation. The ortho and para products are favored due to the electron-donating nature of the ethyl group, which stabilizes the intermediate carbocation during the reaction. The meta product is less favored but still possible.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Electrophilic Aromatic Substitution

Electrophilic aromatic substitution (EAS) is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. In the case of ethylbenzene reacting with nitric acid, the nitronium ion (NO2+) acts as the electrophile, leading to the introduction of a nitro group onto the benzene ring. Understanding EAS is crucial for predicting the products formed in this reaction.
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Regioselectivity

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple possibilities exist. In the reaction of ethylbenzene with nitric acid, the position where the nitro group attaches to the benzene ring is influenced by the ethyl group's electron-donating effects, leading to specific regioisomers. Recognizing regioselectivity helps in identifying the major products of the reaction.

Nomenclature of Aromatic Compounds

Nomenclature of aromatic compounds involves the systematic naming of organic molecules based on established rules, such as those set by the International Union of Pure and Applied Chemistry (IUPAC). For the products formed from the reaction of ethylbenzene and nitric acid, understanding how to name the resulting nitro-ethylbenzenes is essential for clear communication in chemistry. This includes recognizing the positions of substituents on the benzene ring.
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