Answer the question on the basis of passage given below: Strong oxidizing agents, oxidize toluene and its derivatives to benzoic acid. However, it is possible to stop the oxidation at the aldehyde stage with suitable reagents that convert methyl group to an intermediate that is difficult to oxidize further. |
A here is: |
No reaction
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No reaction |
The correct answer is option 3. No reaction. The given reactant in the question is 2-methyl-2-phenylpropane. Let us break down the explanation step by step to understand why 2-methyl-2-phenylpropane (also known as tert-butylbenzene) does not undergo oxidation. The structure of 2-methyl-2-phenylpropane is:
In this structure: The central carbon atom (which is the "2-position" carbon) is bonded to three other groups: Two methyl groups (\( \text{-CH}_3 \)). One phenyl group (\( \text{-C}_6\text{H}_5 \)). This central carbon is known as a tertiary carbon because it is bonded to three other carbon atoms and has no hydrogen atoms attached directly to it. Oxidation Reactions and Carbon Atoms: Oxidation typically involves either: Removal of hydrogen atoms from a carbon atom. Addition of oxygen atoms to a carbon atom. In organic chemistry, oxidation reactions often transform: Primary alcohols \((R-CH_2OH)\) into aldehydes or carboxylic acids. Secondary alcohols \((R_2CHOH)\) into ketones. Hydrocarbons into various oxidation products like alcohols, aldehydes, ketones, or acids depending on the structure. Lack of Hydrogen Atoms on the Tertiary Carbon: The central carbon in 2-methyl-2-phenylpropane is a tertiary carbon. For an oxidation reaction to occur, there typically needs to be hydrogen atoms attached to the carbon atom that is being oxidized. In 2-methyl-2-phenylpropane, the tertiary carbon does not have any hydrogen atoms attached to it—only carbon-carbon bonds \((C-C)\). Without hydrogen atoms, there are no protons available to be removed, which is a necessary step in most oxidation reactions. Stability of Tertiary Carbons: Tertiary carbons are generally more stable than primary or secondary carbons because they are surrounded by more carbon groups, which helps to stabilize the molecule. This stability means that tertiary carbons are less reactive and less likely to participate in oxidation reactions. Primary and Secondary Alcohols or Hydrocarbons: In primary or secondary alcohols (like ethanol or isopropanol), the carbon attached to the -OH group has hydrogen atoms that can be removed during oxidation, allowing these compounds to be oxidized to aldehydes, ketones, or acids. For example: Ethanol (a primary alcohol) can be oxidized to acetaldehyde or acetic acid. Isopropanol (a secondary alcohol) can be oxidized to acetone. 2-Methyl-2-phenylpropane (Tertiary): Unlike primary or secondary alcohols, 2-methyl-2-phenylpropane does not have the necessary hydrogen atoms on the carbon that would typically be oxidized. Therefore, standard oxidizing agents like potassium permanganate (\( \text{KMnO}_4 \)) or chromic acid (\( \text{H}_2\text{CrO}_4 \)) will not be able to oxidize this compound under normal conditions. Conclusion: 2-Methyl-2-phenylpropane (tert-butylbenzene) does not undergo oxidation because it has a tertiary carbon center that lacks hydrogen atoms. Oxidation reactions typically require the presence of hydrogen atoms on the carbon being oxidized, and the absence of these hydrogen atoms in this molecule makes it resistant to oxidation under standard conditions. |