Chapter 3: Problem 25
There are seven constitutional isomers with the formula \(\mathrm{C}_{4} \mathrm{H}_{10} \mathrm{O}\). Draw as many as you can.
Short Answer
Expert verified
There are seven constitutional isomers for \( \mathrm{C}_{4}\mathrm{H}_{10}\mathrm{O} \).
Step by step solution
01
Understanding Constitutional Isomers
Constitutional isomers have the same molecular formula but different connectivity of atoms. For the formula \( \mathrm{C}_{4}\mathrm{H}_{10}\mathrm{O} \), we need to explore different ways to connect four carbon atoms, ten hydrogen atoms, and one oxygen atom.
02
Identifying Carbon Skeletons
Consider the possible carbon backbones. For four carbon atoms, we can have a straight chain \( (\text{butane}) \) or a branched chain \( (\text{isobutane}) \).
03
Exploring Oxygen Positions in Butane
Place the oxygen within the straight chain of butane. You can attach the oxygen to a terminal carbon as an alcohol (1-butanol) or to an internal carbon (2-butanol). Also, placing oxygen as ethers can create 1-methoxypropane and 2-methoxypropane.
04
Exploring Oxygen Positions in Isobutane
In isobutane, connect the oxygen as an alcohol to one of the primary carbons (2-methyl-1-propanol) or to the secondary carbon (2-methyl-2-propanol). Lastly, consider ether forms like tert-butyl methyl ether.
05
Drawing Isomers
Compile all unique structures: 1-butanol, 2-butanol, 1-methoxypropane, 2-methoxypropane, 2-methyl-1-propanol, 2-methyl-2-propanol, and tert-butyl methyl ether.
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Molecular Structure
In organic chemistry, the term "molecular structure" refers to the three-dimensional arrangement of atoms within a molecule. Each molecule has a distinct arrangement that defines its physical and chemical properties. For example, when we look at constitutional isomers like the ones with the molecular formula \(\mathrm{C}_4\mathrm{H}_{10}\mathrm{O}\), the atoms are connected in different ways, even though the molecular formula remains the same.
Molecular structure isn’t just about which atoms are in a molecule. It also involves how these atoms are arranged in space and their connectivity. Key points about molecular structure include:
Molecular structure isn’t just about which atoms are in a molecule. It also involves how these atoms are arranged in space and their connectivity. Key points about molecular structure include:
- Atom Connectivity: The sequence in which atoms are bonded together.
- Geometric Arrangement: The 3D orientation of these connected atoms.
- Structural Variations: Different structures lead to different isomers, even for the same molecular formula, affecting properties and reactions.
Organic Chemistry
Organic chemistry is the branch of chemistry that studies carbon-based compounds, primarily composed of carbon and hydrogen atoms. The unique chemistry of carbon allows it to form numerous stable bonds with itself and other elements, creating an almost infinite variety of structures and compounds.
In the exploration of constitutional isomers, organic chemists focus on how atoms are rearranged to create distinct molecules with different properties. The study of these compounds often involves several concepts, including:
In the exploration of constitutional isomers, organic chemists focus on how atoms are rearranged to create distinct molecules with different properties. The study of these compounds often involves several concepts, including:
- Functional Groups: Specific groups of atoms within molecules that are responsible for the characteristic reactions of those molecules. In \(\mathrm{C}_4\mathrm{H}_{10}\mathrm{O}\), functional groups like alcohols and ethers are explored.
- Stereochemistry: The study of spatial arrangements of atoms in molecules and how this affects their chemical behavior, crucial in differentiating isomers.
- Mechanisms of Reactions: Detailed step-by-step procedures showing the progression from reactants to products. Reaction mechanisms often depend heavily on the molecular structure of the compounds involved.
Carbon Connectivity
Carbon connectivity refers to the various ways through which carbon atoms in a molecule are linked. This connectivity is the foundation for creating structural diversity in organic compounds. In the world of constitutional isomers, different linkages create different isomer configurations for the same molecular formula.
For example, with the seven constitutional isomers of \(\mathrm{C}_4\mathrm{H}_{10}\mathrm{O}\), the connectivity changes lead to different skeletons, such as butane and isobutane, impacting the molecular structure and corresponding physical and chemical properties.
For example, with the seven constitutional isomers of \(\mathrm{C}_4\mathrm{H}_{10}\mathrm{O}\), the connectivity changes lead to different skeletons, such as butane and isobutane, impacting the molecular structure and corresponding physical and chemical properties.
- Straight Chain Carbon Connectivity: All carbon atoms are connected in a row; an example is the straight butane chain.
- Branched Chain Carbon Connectivity: Some carbon atoms connect to others at a branch point, leading to structures like isobutane.
- Impact of Connectivity on Properties: This can affect boiling points, solubility, and reactivity.