Problem 97 Draw the condensed structural fo... [FREE SOLUTION]

Chapter 17: Problem 97

Draw the condensed structural formulas and write the IUPAC names for all eight alcohols that have the molecular formula \(\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O} .(17.4)\)

Short Answer

Expert verified

The eight alcohols are 1-Pentanol, 2-Pentanol, 3-Pentanol, 2-Methyl-1-butanol, 3-Methyl-1-butanol, 3-Methyl-2-butanol, 2-Methyl-2-butanol, and tert-Pentanol.

Step by step solution

- Determine the structure of the carbon chain

Identify all potential carbon chain structures for a molecule with the formula \( \text{C}_5 \text{H}_{12} \text{O} \). These include linear, branched, and corresponding isomers.

- Identify the positions for the hydroxyl group (鈥揙H)

For each carbon chain structure, determine all possible locations for the 鈥揙H group. Remember it can be attached to different carbon atoms.

- Draw the condensed structural formulas

For each isomer identified in the previous steps, draw their condensed structural formulas. This involves writing out the carbon and hydrogen layout along with the 鈥揙H group for each configuration.

- Name each structure according to IUPAC rules

Assign IUPAC names to each isomer. This includes identifying the longest carbon chain and numbering it in such a way that the 鈥揙H group gets the lowest possible number.

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Key Concepts

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

Condensed Structural Formulas

A condensed structural formula provides a straightforward way to represent a molecule without drawing all the individual bonds between atoms. It's a shorthand notation that still conveys detailed information about the structure. It shows the sequence of carbon (C) atoms and any hydrogen (H) atoms attached to them, as well as the functional groups like hydroxyl (鈥揙H) in the molecule. For the alcohols with the molecular formula \(\text{C}_5 \text{H}_{12} \text{O}\), write the condensed structural formulas as follows:

颁贬袄迟别虫迟蝉耻产蝉肠谤颈辫迟调3皑鈥�(颁贬袄迟别虫迟蝉耻产蝉肠谤颈辫迟调2皑)袄迟别虫迟蝉耻产蝉肠谤颈辫迟调4皑鈥揙贬
颁贬袄迟别虫迟蝉耻产蝉肠谤颈辫迟调3皑鈥揅贬袄迟别虫迟蝉耻产蝉肠谤颈辫迟调2皑鈥揅贬(翱贬)鈥揅贬袄迟别虫迟蝉耻产蝉肠谤颈辫迟调2皑鈥揅贬袄迟别虫迟蝉耻产蝉肠谤颈辫迟调3皑

Continue this process to cover all eight possible isomers. Break each formula where the hydroxyl group is attached to different carbons or result in branching.

IUPAC Naming

IUPAC naming is the standardized method to name chemical compounds. It ensures each compound has a unique and universally accepted name. To assign IUPAC names for alcohols with the formula \(\text{C}_5 \text{H}_{12} \text{O}\), follow these steps:

Identify the longest carbon chain that includes the 鈥揙H group.
Number the chain so that the carbon with the 鈥揙H group gets the lowest number.
Name the compound by adding the suffix 鈥�-ol鈥� to the name of the parent hydrocarbon.

For example, for the chain CH\textsubscript{3}鈥揅H\textsubscript{2}鈥揅H\textsubscript{2}鈥揅H\textsubscript{2}鈥揅H\textsubscript{2}鈥揙H, the longest chain is five carbons (pentane), and the 鈥揙H group is on carbon 1, thus the name is pentan-1-ol. Be sure to properly name each different isomer resulting from different positions of the 鈥揙H group.

Isomer Identification

Isomers are compounds that have the same molecular formula but different structures. Here, we identify structural isomers for \(\text{C}_5 \text{H}_{12} \text{O}\), which are molecules that contain the same combination of atoms but arranged in distinct configurations. To identify the isomers:

Draw all the unique carbon skeletons for five carbons, considering both straight and branched chains.
For each skeleton, place the hydroxyl (鈥揙H) group on every possible carbon atom except where it would result in the same molecule after counting from the other end.

For instance, straight-chain pentan-1-ol and pentan-2-ol are different because the 鈥揙H group is at different carbons. Once you have identified the chains and all positions for the hydroxyl group, you can correctly determine the eight isomers.

Hydroxyl Group Positions

The position of the hydroxyl group is critical in the identification and naming of alcohol isomers. Its placement affects the properties and the name of the alcohol:

For a linear chain like pentane, the 鈥揙H group can be placed on carbons 1, 2, or 3, resulting in different isomers (pentan-1-ol, pentan-2-ol, and pentan-3-ol, though pentan-3-ol mirrors the structure of pentan-2-ol viewed from the other end).
For branched chains like 2-methylbutane, the 鈥揙H group can be placed on different carbons yielding 2-methylbutan-1-ol or 2-methylbutan-2-ol. Each position results in distinct properties and names for the molecule.

By systematically placing the hydroxyl group in all possible positions while considering symmetry and carbon chain branching, you can ensure that all unique isomers are identified and named correctly.

91影视

Draw the condensed structural formulas and write the IUPAC names for all eight alcohols that have the molecular formula \(\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O} .(17.4)\)

Short Answer

Step by step solution

- Determine the structure of the carbon chain

- Identify the positions for the hydroxyl group (鈥揙H)

- Draw the condensed structural formulas

- Name each structure according to IUPAC rules

Key Concepts

Condensed Structural Formulas

IUPAC Naming

Isomer Identification

Hydroxyl Group Positions

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