Question

Write the structural formulas for as many alcohols as you can think of thathave empirical formula \(\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{O}\).

Short answer

The three possible structural formulas for alcohols with an empirical formula of \(\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{O}\) are: 1. Propan-1-ol: \(\mathrm{CH}_{3}\) - \(\mathrm{CH}_{2}\) - \(\mathrm{CH}_{2}\) \(\mathrm{OH}\) 2. Propan-2-ol: \(\mathrm{CH}_{3}\) - \(\mathrm{CH}\) (\(\mathrm{OH}\)) - \(\mathrm{CH}_{3}\) 3. 2-methylpropan-2-ol: \(\mathrm{CH}_{3}\) - \(\mathrm{C}\) (\(\mathrm{CH}_{3}\)) (\(\mathrm{OH}\)) - \(\mathrm{CH}_{3}\)

Step-by-step solution

Identify possible carbon arrangements

For a molecule with three carbon atoms, there are two possible arrangements, which are linear or branched. Now let's add hydrogen atoms and an oxygen atom to create alcohols following these arrangements.

Linear arrangement

The linear arrangement involves three carbon atoms placed sequentially. In order to create an alcohol, we need to add the OH functional group to one of the carbon atoms. There are two primary possibilities, with the OH group attached at the first or second carbon atom: 1. Propan-1-ol: \(\mathrm{CH}_{3}\) - \(\mathrm{CH}_{2}\) - \(\mathrm{CH}_{2}\) \(\mathrm{OH}\) 2. Propan-2-ol: \(\mathrm{CH}_{3}\) - \(\mathrm{CH}\) (\(\mathrm{OH}\)) - \(\mathrm{CH}_{3}\)

Branched arrangement

The branched arrangement involves having two carbon atoms in the main chain and one carbon atom branching off. When creating an alcohol with this arrangement, the OH group can only be placed on one carbon (the central carbon), resulting in only one possible structure: 3. 2-methylpropan-2-ol: \(\mathrm{CH}_{3}\) - \(\mathrm{C}\) (\(\mathrm{CH}_{3}\)) (\(\mathrm{OH}\)) - \(\mathrm{CH}_{3}\) Here are the three possible structural formulas for alcohols with an empirical formula of \(\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{O}\): 1. Propan-1-ol: \(\mathrm{CH}_{3}\) - \(\mathrm{CH}_{2}\) - \(\mathrm{CH}_{2}\) \(\mathrm{OH}\) 2. Propan-2-ol: \(\mathrm{CH}_{3}\) - \(\mathrm{CH}\) (\(\mathrm{OH}\)) - \(\mathrm{CH}_{3}\) 3. 2-methylpropan-2-ol: \(\mathrm{CH}_{3}\) - \(\mathrm{C}\) (\(\mathrm{CH}_{3}\)) (\(\mathrm{OH}\)) - \(\mathrm{CH}_{3}\)

Key concepts

Empirical Formula

An empirical formula represents the simplest whole-number ratio of atoms in a chemical compound. It is important to understand that the empirical formula does not provide specific information about the arrangement or the number of atoms in each molecule. Instead, it offers a basic overview of the types and relative amounts of atoms present.
For example, in the exercise, the empirical formula for the alcohols is given as \(\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{O}\). This formula tells us that each unit of these alcohols, in its simplest form, contains 3 carbon, 6 hydrogen, and 1 oxygen atom. However, without additional structural data, we cannot know how these atoms are arranged. This is why the structural formulas are crucial—they allow us to visualize how these atoms connect to form different alcohol isomers. When analyzing compounds, it starts with identifying the empirical formula to understand what elements are present and in what proportion.

Propanol Isomers

Isomers are compounds that have the same chemical formula but differ in the arrangement of their atoms. For propanol, we have several isomers due to different ways the carbon skeleton can be arranged and where the hydroxyl (OH) group is attached.
Propanol isomers derived from the empirical formula \(\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{O}\) include structural variations:

• Propan-1-ol: This is a linear form where the OH group attaches to the first carbon atom, resulting in the structure \(\mathrm{CH}_{3} - \mathrm{CH}_{2} - \mathrm{CH}_{2} \mathrm{OH}\).
• Propan-2-ol: Here, the OH is on the second carbon in the linear chain, represented as \(\mathrm{CH}_{3} - \mathrm{CH}(\mathrm{OH}) - \mathrm{CH}_{3}\).
• 2-methylpropan-2-ol: This is a branched isomer where the central carbon carries both methyl and hydroxyl groups, creating \(\mathrm{CH}_{3} - \mathrm{C}(\mathrm{CH}_{3})(\mathrm{OH}) - \mathrm{CH}_{3}\).

Understanding these isomers helps in grasping how flexible the structures can be even with the same empirical formula. This structural diversity is crucial in organic chemistry for identifying chemical properties and potential reactivity.

Functional Groups

Functional groups are specific groups of atoms responsible for the characteristic chemical reactions of those molecules. In alcohols, the key functional group is the hydroxyl group \(\mathrm{OH}\).
Functional groups define the behavior of molecules in chemical reactions. In our case, alcohols all share the hydroxyl group, which can significantly influence their physical properties, such as boiling point and solubility, and chemical reactivity. When looking at alcohols:

• The placement of the hydroxyl group within a molecule can create different isomers, as seen in the propanol example.
• Functional groups impact naming conventions in organic chemistry, such as 'propanol' indicating the presence of a 3-carbon chain with an \(\mathrm{OH}\) group.
• The number and position of functional groups contribute to the classification and identification of molecules.

By recognizing the functional groups present in a compound, chemists can predict the types of reactions that the compound can undergo, which is pivotal in synthesis and analysis.