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Chapter 21: Problem 29

Give the structure of each of the following aromatic hydrocarbons. a. \(o\) -ethyltoluene b. \(p\) -di-tert-butylbenzene c. \(m\) -diethylbenzene d. \(1-\) phenyl- 2 -butene

Short Answer

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Step by step solution

01

Understand IUPAC Nomenclature

The IUPAC naming system for organic compounds is a standardized method for naming organic molecules based on the main carbon chain and the attached functional groups. The prefixes "ortho" (o), "meta" (m), and "para" (p) are used to describe the relative positions of substituents on the benzene ring. Ortho- means the substituents are on adjacent carbon atoms, meta- means they are separated by one carbon atom, and para- means they are opposite to each other. Additionally, numbers may also be used to indicate the positions more explicitly. Now let's draw the structures for each given aromatic hydrocarbon.
02

Draw the Structure of o-ethyltoluene

First, identify the main structure as a benzene ring. Toluene has a methyl group (CH₃) attached to the benzene ring. In o-ethyltoluene, an ethyl group (CH₂CH₃) is also attached to the benzene ring ortho- to the methyl group (i.e., adjacent to the methyl group). The structure of o-ethyltoluene is: ![o-ethyltoluene](https://www.cheminfo.org/flavor-molecules/records/o-ethyltoluene/index.files/mol.svg)
03

Draw the Structure of p-di-tert-butylbenzene

Start with a benzene ring. In this case, two tert-butyl groups (C(CH₃)₃) are positioned para- to each other (i.e., opposite to each other) on the benzene ring. The structure of p-di-tert-butylbenzene is: ![p-di-tert-butylbenzene](https://upload.wikimedia.org/wikipedia/commons/thumb/9/9f/Para-Di-tert-butylbenzene-2D-skeletal.png/320px-Para-Di-tert-butylbenzene-2D-skeletal.png)
04

Draw the Structure of m-diethylbenzene

Again, start with a benzene ring. For m-diethylbenzene, there are two ethyl groups (CH₂CH₃) attached to the benzene ring in meta-positions (i.e., separated by one carbon atom). The structure of m-diethylbenzene is: ![m-diethylbenzene](https://upload.wikimedia.org/wikipedia/commons/thumb/c/c6/M_diethyl_benzene.PNG/1280px-M_diethyl_benzene.PNG)
05

Draw the Structure of 1-phenyl-2-butene

In this case, we have a butene molecule (four carbon atoms in a chain with a double bond between the 2nd and 3rd carbons). The 1-phenyl- part indicates that a benzene ring (phenyl group) is attached to the first carbon of the butene chain. The structure of 1-phenyl-2-butene is: ![1-phenyl-2-butene](https://assets0.pubchem.ncbi.nlm.nih.gov/image/imagefly.cgi?regid=70355%2C&conf=3%2C&id=2028%2C=375%2CIMAGE_THUMBNAIL)

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