Question

Tertiary alcohols are resistant to oxidation because the carbon bearing the - OH is already bonded to three carbon atoms and, therefore, cannot form an additional caubon-axygen bond. 1-Methylcyclopentanod Thus, the prerequisite for the oxidation of an alcohol to an aldehyde or ketone is at least one Hon the carbon bearing the OH gromp.

Short answer

Answer: Tertiary alcohols are resistant to oxidation because the carbon attached to the -OH group is already bonded to three other carbon atoms, leaving no room for forming an additional carbon-oxygen bond. In order for an alcohol to be oxidized to an aldehyde or ketone, there must be at least one hydrogen atom on the carbon bearing the -OH group to ensure a carbon-hydrogen bond can be broken and a new carbon-oxygen bond can be formed.

Step-by-step solution

Understand the structure of tertiary alcohols

Tertiary alcohols are those alcohols in which the carbon atom attached to the hydroxyl group (-OH) is bonded to three other carbon atoms. In other words, the carbon bonded to the -OH group is tertiary (3°) carbon.

Observe the resistance of tertiary alcohols to oxidation

For oxidation of alcohol to occur and form an aldehyde or a ketone, there must be a possibility of forming a new carbon-oxygen double bond (C=O) by removing hydrogen atoms from the carbon bearing the -OH group. Since in tertiary alcohols, the carbon bonded to the -OH is already connected to three other carbon atoms, there is no possibility of bond formation to oxygen by breaking an existing carbon-hydrogen bond. This implies that tertiary alcohols cannot be easily oxidized into aldehydes or ketones. Tertiary alcohols are thus resistant to oxidation.

Learn the prerequisite for oxidation of an alcohol to aldehyde or ketone

In order for an alcohol to be oxidized to an aldehyde or ketone, there must be at least one hydrogen atom on the carbon bearing the -OH group. This ensures that during oxidation, it is possible to break the carbon-hydrogen bond and form a new carbon-oxygen bond. For example, if we consider a primary alcohol, the carbon bonded to the -OH group is also bonded to only one other carbon atom and contains two hydrogen atoms. During oxidation, one of the carbon-hydrogen bonds will be broken, and a carbon-oxygen double bond will be formed, yielding an aldehyde. Similarly, in the case of secondary alcohols, the carbon bonded to the -OH group is attached to two other carbons and has one hydrogen atom bonded to it. This results in the formation of a ketone upon oxidation by breaking the carbon-hydrogen bond and forming a carbon-oxygen double bond.

Conclusion

Tertiary alcohols are resistant to oxidation because the carbon bearing the -OH group is already bonded to three carbon atoms, and therefore, no additional carbon-oxygen bond can be formed. For oxidation of an alcohol to an aldehyde or ketone to occur, there must be at least one hydrogen atom on the carbon bearing the -OH group.

Key concepts

Oxidation Resistance in Tertiary Alcohols

Understanding the unique chemical properties of different classes of alcohols is crucial for students of chemistry. One of these distinctive characteristics is the oxidation resistance observed in tertiary alcohols. Oxidation is a chemical reaction that involves the loss of electrons or an increase in oxidation state by a molecule, atom, or ion. In the case of alcohols, oxidation typically results in the formation of aldehydes or ketones. However, tertiary alcohols, like 1-Methylcyclopentanol, stand out due to their structural resistance to this transformation.

At the heart of this resistance is the tertiary carbon atom—the carbon connected to the hydroxyl (-OH) group. This carbon is already fully saturated with three carbon bonds, leaving no space or available bonds to form an additional bond with oxygen. Without the flexibility to create a new carbon-oxygen double bond, tertiary alcohols cannot undergo the typical oxidation process that would lead to aldehydes or ketones. Hence, they demonstrate a natural resistance to oxidation which is both protective and limiting from a chemical reactivity standpoint.

Formation of Carbon-Oxygen Double Bond

A fundamental aspect of alcohol oxidation is the formation of a carbon-oxygen double bond—it's the signature move of this chemical phenomenon. For primary and secondary alcohols, this process takes center stage when they are oxidized to become aldehydes and ketones respectively. To form this critical double bond, there must be available hydrogen atoms attached to the carbon with the hydroxyl group that can be removed.

During the oxidation process, specific reagents facilitate the removal of these hydrogen atoms, thus allowing the formation of a double bond between the carbon and oxygen (C=O). This double bond is what defines the new molecules—aldehydes and ketones—as oxidation products. The straightforward breakage of a carbon-hydrogen bond and the subsequent formation of a carbon-oxygen bond underscore the simplicity and elegance of this key chemical transformation. Understanding this central concept helps illuminate why tertiary alcohols, lacking these appointable hydrogen atoms, are resistant to the oxidation process and do not form the characteristic carbon-oxygen double bond.

Prerequisite for Alcohol Oxidation

The oxidation of an alcohol to yield an aldehyde or ketone is not a random occurrence; it follows precise chemical criteria. One of the essential prerequisites for this reaction is the presence of at least one hydrogen atom on the carbon that is bonded to the hydroxyl (-OH) group. This prerequisite comes down to the need for a breakable bond, a removable hydrogen, that can make way for the formation of a carbon-oxygen double bond.

In primary alcohols, the carbon hosting the -OH group has two such hydrogens, paving the way for the formation of an aldehyde. In secondary alcohols, one hydrogen is present, which allows the creation of a ketone. This requirement is a perfect example of how something as small as a single hydrogen atom can dictate the path and products of a chemical reaction. By highlighting this condition in the classroom, educators can help students appreciate the role of molecular structure in the reactivity and transformations of organic compounds. Consequently, it becomes clear why tertiary alcohols, with no hydrogens on the carbon attached to the -OH group, are spared from undergoing this specific oxidative fate.