For the oxidation of diphenylmethanol, shown below, which of the following statements is false?[Fill in the blank]

Question

BlackTom AI · Accepted Answer

To tackle this question, I will examine each provided statement about the oxidation of diphenylmethanol to the corresponding ketone, addressing what is true or false based on standard oxidation chemistry and structural implications.

Option a: 'The oxidation of diphenylmethanol involves replacing a C–H bond with a C–O bond.' In an oxidation of a secondary alcohol to a ketone, the carbon bearing the hydroxyl group loses the hydrogen (and the oxygen forms a carbonyl). Conceptually, one can view this as removing a C–H and forming a C=O bond, which involves incorporating oxygen into the bond framework and changing the carbon's oxidation state. This statement captures the essential bond-change idea and is consistent with this oxidation type, so it is correct.

Option b: 'The ketone product only contains sp2 hybridised carbon centres.' The ketone product in this case is benzophenone (diphenyl methyl ketone), where the carbonyl carbon is sp2-hybridized, and the aromatic rings are comprised of sp2 carbons as well. There are no sp3 carbons in the benzophenone skeleton. Therefore this statement is true.

Option c: 'The oxidation of diphenylmethanol to the ketone product will result in an increase in the number of C–H bonds in the ketone product.' Here we consider the change in hydrogen count on the carbon framework. In diphenylmethanol, the carbon attached to the OH bears one hydrogen (CH–OH). After oxidation to the ketone, that carbon becomes the carbonyl carbon with no hydrogens (C=O attached to two phenyl groups). Consequently, the total number of C–H bonds in the product is not increased; it is actually decreased at that carbon. This makes the statement false, since oxidation to a ketone does not increase the C–H bond count; it reduces it at the oxidized carbon.

Option d: 'Oxidation of diphenylmethanol gives the ketone product.' This is the defining outcome of this oxidation sequence (secondary alcohol to ketone). The statement is true by standard organic chemistry.

In summary, each option was evaluated for how it aligns with the structural and mechanistic realities of oxidizing a secondary alcohol to a ketone, including bond changes, hybridization, and hydrogen accounting. The analysis shows that the claim about increasing C–H bonds (Option c) does not hold under these oxidation conditions, while the other statements accurately describe aspects of the process and product.

For the oxidation of diphenylmethanol, shown below, which of the following statements is false?[Fill in the blank]

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