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Ch. 18 - Reactions of Benzene and Substituted Benzenes
Bruice - Organic Chemistry 8th Edition
Bruice8th EditionOrganic ChemistryISBN: 9780135213711Not the one you use?Change textbook
Chapter 19, Problem 45a

Draw the structure for each of the following:
a. m-ethylphenol

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1
Step 1: Understand the naming convention. The prefix 'm-' stands for 'meta-', which indicates the relative position of substituents on a benzene ring. In a meta-substitution, the substituents are located at positions 1 and 3 on the benzene ring.
Step 2: Identify the substituents. The name 'm-ethylphenol' indicates two substituents: an ethyl group (-CH₂CH₃) and a hydroxyl group (-OH). The 'phenol' part of the name means the hydroxyl group is directly attached to the benzene ring.
Step 3: Assign the positions of the substituents. The hydroxyl group (-OH) is at position 1 (as it is the defining group of phenol), and the ethyl group (-CH₂CH₃) is at position 3 relative to the hydroxyl group.
Step 4: Draw the benzene ring. Place the hydroxyl group (-OH) at position 1 and the ethyl group (-CH₂CH₃) at position 3, ensuring the correct meta-relationship between the two substituents.
Step 5: Verify the structure. Double-check that the substituents are correctly placed in the meta-positions (1 and 3) and that the benzene ring is intact with alternating double bonds.

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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 that exhibit resonance stability due to the delocalization of π electrons across the ring structure. They typically follow Huckel's rule, which states that a compound must have (4n + 2) π electrons to be considered aromatic. Understanding the properties of aromaticity is crucial for drawing structures like m-ethylphenol, which contains a benzene ring.
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Substituent Positioning

In organic chemistry, the positioning of substituents on a benzene ring is described using ortho (adjacent), meta (one carbon apart), and para (opposite) nomenclature. For m-ethylphenol, the 'm' indicates that the ethyl group and the hydroxyl group (from phenol) are positioned at the meta positions relative to each other. This understanding is essential for accurately representing the molecular structure.
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Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In m-ethylphenol, the hydroxyl (-OH) group is the functional group that defines its properties as a phenol. Recognizing functional groups is vital for predicting reactivity and understanding the compound's behavior in chemical reactions.
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