Chapter 3: Problem 26
Calculate the degrees of unsaturation \((\Omega)\) for the following formulas. Give two possible structures for each one. (a) \(\mathrm{C}_{5} \mathrm{H}_{6}\) (b) \(\mathrm{C}_{7} \mathrm{H}_{8} \mathrm{O}\) (c) \(\mathrm{C}_{7} \mathrm{H}_{10}\) (d) \(\mathrm{C}_{5} \mathrm{H}_{8} \mathrm{Br}_{2}\)
Short Answer
Expert verified
Degrees of unsaturation \(\Omega\): (a) 3, (b) 4, (c) 3, (d) 1. Multiple structures with rings or double bonds are possible.
Step by step solution
01
Understanding Degrees of Unsaturation
Degrees of unsaturation \(\Omega\) can be calculated using the formula: \[ \Omega = C + 1 - \frac{H}{2} - \frac{X}{2} + \frac{N}{2} \] where \(C\) is the number of carbon atoms, \(H\) is the number of hydrogen atoms, \(X\) is the number of halogens, and \(N\) is the number of nitrogen atoms.
02
Calculate \(\Omega\) for \(\mathrm{C}_{5} \mathrm{H}_{6}\)
Substitute the values into the formula: \[ \Omega = 5 + 1 - \frac{6}{2} = 5 + 1 - 3 = 3 \] Therefore, \(\Omega = 3\). This indicates 3 degrees of unsaturation, which could correspond to rings or double bonds.
03
Possible Structures for \(\mathrm{C}_{5} \mathrm{H}_{6}\)
Two possible structures include: 1. A benzene ring with one double bond (1,2-cyclopentadiene). 2. An aromatic ring (Cyclopentatriene).
04
Calculate \(\Omega\) for \(\mathrm{C}_{7} \mathrm{H}_{8} \mathrm{O}\)
Substitute the values into the formula: \[ \Omega = 7 + 1 - \frac{8}{2} = 7 + 1 - 4 = 4 \] Therefore, \(\Omega = 4\). This indicates 4 degrees of unsaturation, which could correspond to rings, double bonds, or combined.
05
Possible Structures for \(\mathrm{C}_{7} \mathrm{H}_{8} \mathrm{O}\)
Two possible structures include: 1. A benzene ring with a methoxy group (methoxybenzene). 2. A benzene ring with a hydroxy group (p-cresol).
06
Calculate \(\Omega\) for \(\mathrm{C}_{7} \mathrm{H}_{10}\)
Substitute the values into the formula: \[ \Omega = 7 + 1 - \frac{10}{2} = 7 + 1 - 5 = 3 \] Therefore, \(\Omega = 3\). This indicates 3 degrees of unsaturation, which could be rings and/or double bonds.
07
Possible Structures for \(\mathrm{C}_{7} \mathrm{H}_{10}\)
Two possible structures include: 1. A benzene ring with one extra double bond (1,3,5-cycloheptatriene). 2. A chain with two double bonds in conjugation (hepta-1,3-diene).
08
Calculate \(\Omega\) for \(\mathrm{C}_{5} \mathrm{H}_{8} \mathrm{Br}_{2}\)
Substitute the values into the formula: \[ \Omega = 5 + 1 - \frac{8}{2} - \frac{2}{2}= 5 + 1 - 4 - 1 = 1 \] Therefore, \(\Omega = 1\). This indicates 1 degree of unsaturation, which could correspond to a ring or double bond.
09
Possible Structures for \(\mathrm{C}_{5} \mathrm{H}_{8} \mathrm{Br}_{2}\)
Two possible structures include: 1. A ring with two bromine atoms (1,2-dibromocyclopentane). 2. A chain with one double bond and two bromine atoms (1-bromo-2-bromobutene).
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Organic Chemistry
Organic chemistry is a fascinating branch of chemical science that focuses on the structure, properties, and reactions of organic compounds and materials. These compounds primarily contain carbon atoms, which can form long chains and complex structures. Understanding organic chemistry is essential because it forms the basis of many industrial, biological, and pharmaceutical processes. Carbons can bond with elements like hydrogen, oxygen, and halogens, leading to a wide variety of molecules with different properties. Most organic compounds are employed in everyday life, from the fuels we use to the medicines we take. This field not only involves the synthesis of compounds but also delves deep into their reactivity and mechanisms. One key concept in organic chemistry is the degree of unsaturation, which provides insights into the types of bonds or rings within a molecule.
Molecular Formula
The molecular formula of a compound gives the number and types of atoms present. For example, \(\text{C}_{5} \text{H}_{6} \) tells us there are 5 carbon atoms and 6 hydrogen atoms. This information helps chemists to determine possible structures and properties of the compound. Molecular formulas differ from empirical formulas, which show the simplest ratio of elements. Knowing the exact molecular formula is essential for calculating the degree of unsaturation, using the formula: \[ \Omega = \text{C} + 1 - \frac{H}{2} - \frac{X}{2} + \frac{N}{2}\ \] where \(\text{C}\) is the number of carbons, \(\text{H}\) is hydrogens, \(\text{X}\) is halogens, and \(\text{N}\) is nitrogens. This equation helps in identifying double bonds, triple bonds, and rings within the structure. For example, the molecular formula \(\text{C}_{7} \text{H}_{8} \text{O}\) leads us to calculate the degrees of unsaturation and consequently infer parts of its structure. By analyzing molecular formulas, chemists can predict the behavior and reactivity of substances.
Chemical Structure
A chemical structure represents the arrangement of atoms within a molecule. This arrangement determines the molecule’s properties and reactivity. Visualizing how atoms are connected in three-dimensional space can provide critical insights into a molecule’s behavior. For instance, different structures can arise from the same molecular formula due to the phenomenon of isomerism. Calculating the degrees of unsaturation is a step towards hypothesizing possible structures. Consider \(\text{C}_{7} \text{H}_{10}\): it can be structured as 1,3,5-cycloheptatriene (a ring with alternating bonds) or as hepta-1,3-diene (a chain with double bonds). These structures, although sharing the same formula, exhibit different reactivities and physical properties. For compounds containing halogens like \(\text{C}_{5} \text{H}_{8} \text{Br}_{2}\), degrees of unsaturation can indicate the presence of rings or double bonds, leading to structures like 1,2-dibromocyclopentane or 1-bromo-2-bromobutene. Understanding chemical structures is fundamental for interpreting molecular behavior and guiding the synthesis of new compounds. Always visualize the molecule to better understand its potential interactions and properties.