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Four (of six possible) dimethylhexanes are named below. Draw the structures of each, and determine which of these isomers has a chiral carbon center. (a) 2,2 -dimethylhexane (b) 2,3 -dimethylhexane (c) 2,4 -dimethylhexane (d) 2,5 -dimethylhexane

Short Answer

Expert verified
The chiral isomer is 2,3-dimethylhexane.

Step by step solution

01

Understanding the Molecule Base

Hexane is a saturated hydrocarbon with six carbon atoms sequenced in a chain. It forms the base structure onto which additional methyl groups are attached to form the given dimethylhexanes.
02

Analyzing 2,2-Dimethylhexane

For 2,2-dimethylhexane, two methyl groups are attached to the second carbon of the hexane chain. This structure results in a molecule with no chiral centers because the second carbon already has two identical methyl groups attached.
03

Analyzing 2,3-Dimethylhexane

In 2,3-dimethylhexane, one methyl group is attached to the second carbon and another to the third carbon. The structure can lead to a chiral carbon at either C-2 or C-3, because each carbon is bonded to four different groups, fulfilling the condition for chirality.
04

Analyzing 2,4-Dimethylhexane

For 2,4-dimethylhexane, a methyl group is attached to the second carbon and another to the fourth carbon. This configuration doesn't necessarily make any carbon chiral, depending on the symmetry of the rest of the molecule.
05

Analyzing 2,5-Dimethylhexane

In the case of 2,5-dimethylhexane, a methyl group on C-2 doesn't make this carbon chiral due to symmetry, nor does a methyl group on C-5 confer chirality due to the nature of the other bonds.
06

Identifying the Chiral Isomer

From the analysis, 2,3-dimethylhexane is the only structure that can contain a chiral center, either on C-2 or C-3, because it can have four different groups attached to those carbons.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Dimethylhexanes
Dimethylhexanes are a subset of hexanes, which are hydrocarbons with the chemical formula C\(_8\)H\(_{18}\). Hexanes are saturated molecules, meaning they contain only single bonds between the carbon atoms. Dimethylhexanes specifically are hexanes with two methyl (CH\(_3\)) groups attached at various positions on the carbon chain.
These variations in the attachment points of methyl groups result in different molecules collectively known as isomers. For example, depending on where the methyl groups are placed, you can have 2,2-dimethylhexane, 2,3-dimethylhexane, and so on. Each unique arrangement creates different physical and chemical properties, despite having the same overall molecular formula.
Understanding the different possible structures of dimethylhexanes can offer insights into their behavior and potential applications in organic chemistry.
Organic Chemistry
Organic chemistry is the branch of chemistry focused on the study of carbon-containing compounds. Most of these compounds also contain hydrogen, with oxygen, nitrogen, sulfur, and halogens as common constituents. This branch is fast-paced and dynamic, exploring everything from biological systems to pharmaceuticals and materials science.
A significant part of organic chemistry involves understanding the structure and reactivity of various functional groups and how they influence molecular behavior. Compounds like dimethylhexanes fall under hydrocarbons, a large class of organic compounds composed entirely of hydrogen and carbon atoms.
In organic chemistry, the study of isomers—compounds with the same molecular formula but different structures—is crucial. Isomers can have drastically different properties and uses, highlighting the importance of structural comprehension in chemistry and related fields.
Structural Isomers
Structural isomers, or constitutional isomers, are molecules that share the same molecular formula but differ in how the atoms are arranged in space. This category of isomers is prevalent in organic chemistry, especially among hydrocarbons like dimethylhexanes.
For instance, 2,2-dimethylhexane and 2,3-dimethylhexane are structural isomers. Although they share the same chemical formula, their properties can be very different because of how the carbon atoms are connected to each other.
Recognizing and drawing the structures of isomers helps chemists predict their physical and chemical properties, which can be vastly different despite having the same types and numbers of atoms. This concept is fundamental in synthesis and analysis within organic chemistry.
Chirality
Chirality is a property of a molecule that makes it non-superimposable on its mirror image. Think of it like your left and right hands: they are mirror images but cannot be perfectly aligned on each other. In molecules, a chiral center typically involves a carbon atom bonded to four different groups.
In the case of dimethylhexanes, chirality can play a critical role in determining the molecule's reactivity and interactions. For example, 2,3-dimethylhexane is the only isomer in the given exercise that can possess a chiral center, because the carbon atoms at positions 2 and 3 can have four different substituents surrounding them.
Chirality is an important concept in chemistry because enantiomers, or chiral isomers, can exhibit very different biological activities and properties. These differences are especially crucial in pharmaceuticals, where one enantiomer can be beneficial while its mirror image can be harmful.

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Most popular questions from this chapter

Maleic acid is prepared by the catalytic oxidation of benzene. It is a dicarboxylic acid; that is, it has two carboxylic acid groups. (a) Combustion of \(0.125 \mathrm{g}\) of the acid gives \(0.190 \mathrm{g}\) of \(\mathrm{CO}_{2}\) and \(0.0388 \mathrm{g}\) of \(\mathrm{H}_{2} \mathrm{O} .\) Calculate the empirical formula of the acid. (b) A 0.261 -g sample of the acid requires 34.60 mL of \(0.130 \mathrm{M} \mathrm{NaOH}\) for complete titration (so that the H ions from both carboxylic acid groups are used). What is the molecular formula of the acid? (c) Draw a Lewis structure for the acid. (d) Describe the hybridization used by the C atoms. (e) What are the bond angles around each \(C\) atom?

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