Identify the statement which is not correct among the following. (a) Acetone exists almost \(100 \%\) in the keto form. (b) Acetylacetone exists considerably in the enol form. (c) Phenol exists almost \(100 \%\) in the enol form. (d) The enol content of \(\mathrm{C}_{6} \mathrm{H}_{c}-\mathrm{COCH}_{2} \mathrm{C}_{6} \mathrm{H}_{5}\) is very low.

Short Answer

Expert verified
a) Acetone exists almost \(100 \%\) in the keto form b) Acetylacetone exists considerably in the enol form c) Phenol exists almost \(100 \%\) in the enol form d) The enol content of \(\mathrm{C}_{6} \mathrm{H}_{c}-\mathrm{COCH}_{2}\mathrm{C}_{6} \mathrm{H}_{5}\) is very low Answer: d) The enol content of \(\mathrm{C}_{6} \mathrm{H}_{c}-\mathrm{COCH}_{2}\mathrm{C}_{6} \mathrm{H}_{5}\) is very low

Step by step solution

01

Understand keto and enol forms

Keto and enol forms are tautomeric forms of a compound. Keto form contains a carbonyl group while enol form contains an alcohol (OH) group and a carbon-carbon double bond. Tautomeric forms exist in equilibrium with each other, and the relative stability of the keto and enol forms determines the percentage of each form present in the equilibrium. In general, the keto form is more stable and the percentage of the enol form is very low for most compounds.
02

Evaluate the given statements

(a) Acetone exists almost \(100 \%\) in the keto form: This statement is correct. Acetone is a simple aldehyde and has no hydrogen on the alpha carbon sandwiched between two carbonyl groups, so there is no possibility for the formation of the enol form. (b) Acetylacetone exists considerably in the enol form: This statement is also correct. Acetylacetone has an alpha hydrogen and can form the enol form through tautomerism. In fact, the enol form is stabilized by intramolecular hydrogen bonding, which makes the percentage of the enol form high for this compound. (c) Phenol exists almost \(100 \%\) in the enol form: Phenol has an OH group directly attached to the aromatic ring, and this structure is already considered the "enol form" of a hypothetical keto form, which is very unstable and does not exist in any significant amount. This statement is also correct. (d) The enol content of \(\mathrm{C}_{6} \mathrm{H}_{c}-\mathrm{COCH}_{2}\mathrm{C}_{6} \mathrm{H}_{5}\) is very low: The given compound is a diketone. It has an alpha hydrogen, and it can form an enol, but the enol is not stabilized by intramolecular hydrogen bonding or resonance in the same way as in acetylacetone. Therefore, the enol content would indeed be expected to be low. However, while the enol content is not very high, it is not extremely low either. Therefore, this statement is less accurate than the others.
03

Identify the incorrect statement

Based on the evaluation of the given statements, we can conclude that statement (d) is the least accurate among them, as the enol content of the mentioned compound is not extremely low but rather moderate.

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