The structure of compound I is :- A

- B

- C

- D

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Correct answer: A
The user wants me to solve a multi-step organic chemistry problem by identifying the structure of compound I. I will solve this by working backward from the products of the reactions.
Step 1: Analyze the reaction of compound J
Compound J reacts with to give benzyl alcohol () and a compound L. This is a classic example of the Cannizzaro reaction. This reaction is characteristic of aldehydes that lack α-hydrogens. In the presence of a strong base (like ), one molecule of the aldehyde is reduced to an alcohol, and another is oxidized to the salt of a carboxylic acid.
Since the reduction product is benzyl alcohol, the aldehyde (J) must be benzaldehyde ().
The full reaction is: So, we have identified:
- J = Benzaldehyde ()
- Product = Benzyl alcohol
- L = Potassium benzoate ()
Step 2: Determine the structure of compound I from ozonolysis
Compound I undergoes ozonolysis (, followed by a workup with ) to produce compounds J and K. Ozonolysis cleaves a double bond and forms two carbonyl () groups. To find the structure of the alkene I, we can reverse the process by taking the two carbonyl products (J and K) and joining their carbonyl carbons with a double bond.
We know J is benzaldehyde (). This means one part of the alkene I must have the structure .
Step 3: Evaluate the options based on the structure of I
Let's perform a hypothetical ozonolysis on each of the given options to see which one yields benzaldehyde (J) as one of the products.
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Option A: This reaction gives benzaldehyde (J) and benzophenone (K). This fits our analysis. Let's check the other steps for consistency. Compound K is benzophenone. Benzophenone has no α-hydrogens but is a ketone, so it does not undergo the Cannizzaro reaction. The statement "K on reaction with gives only M" is consistent with K being unreactive under these conditions, so M would be K itself. The contrast is that J gives two products, while K gives only one (itself).
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Option B: The products are benzophenone and acetophenone. Neither of these can be J (benzaldehyde). Thus, this option is incorrect.
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Option C: This reaction gives two molecules of benzaldehyde. So, J and K would be identical. While this would satisfy the condition for J, the problem describes the reactions of J and K in a way that suggests they are different compounds ("J...gives...L, whereas K...gives only M"). This makes this option less plausible than A.
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Option D: The product is two molecules of acetophenone. This cannot be J. Thus, this option is incorrect.
Based on this analysis, Option A is the only one that is fully consistent with the ozonolysis and Cannizzaro reaction steps.
Step 4: Verify the formation of I from a tertiary alcohol H
The first step in the sequence is the acid-catalyzed dehydration of a tertiary alcohol H to form the alkene I. Let's check if the alkene from Option A, , can be formed from a tertiary alcohol.
Consider the tertiary alcohol 1,2,2-triphenylethanol: . Upon treatment with acid (), the -OH group is protonated and leaves as a water molecule, forming a stable tertiary carbocation: Elimination of a proton from the adjacent carbon () gives the desired alkene I: Since a suitable tertiary alcohol precursor (H) exists, this final condition is also met.
Conclusion
The structure of compound I that fits all the described reactions is given in Option A.
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