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Ch.12 Introduction to Organic Chemistry: Alkanes
McMurry - Fundamentals of GOB 8th Edition
McMurry8th EditionFundamentals of GOBISBN: 9780134015187Not the one you use?Change textbook
Chapter 12, Problem 35c

Propose structures for molecules that fit the following descriptions:
(c) An aromatic compound that is also an ether, C8H10O

Verified step by step guidance
1
Step 1: Recall the definition of an aromatic compound. Aromatic compounds contain a benzene ring or a similar conjugated cyclic structure that follows Huckel's rule (4n + 2 π electrons, where n is an integer).
Step 2: Understand the functional group 'ether'. An ether contains an oxygen atom bonded to two alkyl or aryl groups (R-O-R').
Step 3: Combine the aromatic and ether characteristics. The molecule must have a benzene ring (aromatic) and an oxygen atom bonded to two groups, one of which can be the benzene ring itself.
Step 4: Use the molecular formula C8H10O to guide the structure. The benzene ring contributes C6H6, leaving C2H4O for the ether group. This suggests the ether group could be an -OCH3 (methoxy) or -OCH2CH3 (ethoxy) group attached to the benzene ring.
Step 5: Propose possible structures. For example, one structure could be anisole (methoxybenzene), where a methoxy group (-OCH3) is attached to the benzene ring. Another possibility is ethoxybenzene, where an ethoxy group (-OCH2CH3) is attached to the benzene ring.

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Key Concepts

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

Aromatic Compounds

Aromatic compounds are a class of cyclic compounds characterized by their stable ring structure and delocalized pi electrons, which follow Hückel's rule (4n + 2 pi electrons). These compounds often exhibit unique chemical properties, such as increased stability and distinct reactivity patterns, making them essential in organic chemistry.
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Ethers

Ethers are organic compounds that contain an oxygen atom connected to two alkyl or aryl groups, represented by the general formula R-O-R'. They are known for their relatively low reactivity and are commonly used as solvents in organic reactions. The presence of the ether functional group influences the physical and chemical properties of the molecule.
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Molecular Formula and Structure

The molecular formula C8H10O indicates that the compound consists of eight carbon atoms, ten hydrogen atoms, and one oxygen atom. Understanding how to derive the structural representation from the molecular formula is crucial, as it helps in visualizing the arrangement of atoms and functional groups, which is essential for identifying the compound's properties and reactivity.
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