Ch.12 Alcohols, Thiols, Ethers, Aldehydes, and Ketones

Timberlake - Chemistry: An Introduction to General, Organic, and Biological Chemistry 14th Edition

Timberlake14th EditionChemistry: An Introduction to General, Organic, and Biological ChemistryISBN: 9781292472249Not the one you use?Change textbook

Timberlake 14th Edition

Ch.12 Alcohols, Thiols, Ethers, Aldehydes, and Ketones

Problem 48d

Chapter 12, Problem 48d

Draw the condensed structural formula, or line-angle formula if cyclic, for each of the following: (12.1)
d. 2,4-dibromophenol

Verified step by step guidance

Identify the base structure: The name '2,4-dibromophenol' indicates that the compound is based on a benzene ring (a cyclic aromatic structure) with substituents attached.

Determine the substituents: The 'phenol' part of the name means there is an -OH group attached to the benzene ring. The '2,4-dibromo' indicates that there are bromine (Br) atoms attached to the 2nd and 4th positions of the benzene ring.

Assign positions on the benzene ring: Number the carbon atoms in the benzene ring starting from the carbon attached to the -OH group as position 1. Then, assign the bromine atoms to positions 2 and 4 based on the name.

Draw the condensed structural formula: Represent the benzene ring as a hexagon with alternating double bonds. Attach the -OH group to position 1 and bromine atoms to positions 2 and 4. Use condensed notation for clarity.

Alternatively, draw the line-angle formula: Represent the benzene ring as a hexagon with vertices for carbon atoms. Add the -OH group and bromine atoms at the appropriate positions using lines or symbols to indicate bonds.

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Key Concepts

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

Condensed Structural Formula

A condensed structural formula is a way of representing a chemical compound that shows the arrangement of atoms and the connectivity between them without depicting all the bonds explicitly. It typically groups atoms together to indicate how they are connected, making it easier to visualize the structure of the molecule in a compact form.

Line-Angle Formula

The line-angle formula, also known as the skeletal formula, is a shorthand representation of organic molecules where vertices represent carbon atoms and lines represent bonds. This method simplifies the drawing of complex structures, especially cyclic compounds, by omitting hydrogen atoms and focusing on the connectivity of the carbon skeleton.

Substituents in Aromatic Compounds

Substituents are atoms or groups of atoms that replace hydrogen atoms in an aromatic compound, affecting its chemical properties and reactivity. In the case of 2,4-dibromophenol, the 'dibromo' indicates two bromine atoms are attached to the benzene ring at the second and fourth positions, while 'phenol' indicates the presence of a hydroxyl (-OH) group, which influences the compound's acidity and overall behavior.

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