Compound H is formed by the reaction of- A

- B

- C

- D

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Correct answer: C
This is a multi-step organic synthesis problem that requires working backwards from the final products to identify the initial tertiary alcohol H and its reactants.
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Analyze the reactions of J and K:
- Compound J reacts with KOH to give benzyl alcohol and compound L. This is a characteristic Cannizzaro reaction. The Cannizzaro reaction is a disproportionation of an aldehyde that has no α-hydrogens in the presence of a strong base. The products are an alcohol and a carboxylate salt. For benzyl alcohol () to be a product, compound J must be benzaldehyde (). Compound L would be potassium benzoate ().
- Compound K reacts with KOH to give only M. This is also described in a way that suggests a Cannizzaro reaction, which would mean K is also an aldehyde with no α-hydrogens. Acetone, for example, has α-hydrogens and would undergo an aldol condensation. The phrasing 'gives only M' is slightly ambiguous but points away from an equilibrium reaction like aldol condensation.
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Determine the structure of alkene I:
- Alkene I undergoes ozonolysis (, then workup) to produce J (benzaldehyde) and K. Ozonolysis cleaves a C=C double bond and converts the carbons into carbonyl groups.
- Since one product is benzaldehyde (), one part of the alkene must be a group.
- Therefore, the structure of I must be of the form .
- Ozonolysis of this structure yields (benzaldehyde) and (a ketone).
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Address the contradiction:
- From step 1, the reaction of K suggests it is an aldehyde with no α-hydrogens. From step 2, ozonolysis of the deduced structure of I implies K must be a ketone.
- This is a contradiction in the problem statement. The most likely error is in the description of the reaction of K. Ketones (like acetone) with α-hydrogens undergo aldol condensation with KOH, not a Cannizzaro reaction. Let's proceed by assuming the description of K's reaction is flawed and see if we can find a consistent path for the rest of the problem.
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Find a consistent pathway for H, I, and J:
- We need to find a tertiary alcohol H that, upon acid-catalyzed dehydration, gives an alkene I of the form .
- Let's test the options by seeing what tertiary alcohol H they form and what its dehydration product is.
- Option C: Reactants are benzylmagnesium bromide () and acetone ().
- Formation of H: . Compound H is 2-methyl-1-phenyl-2-propanol, which is a tertiary alcohol. This matches the problem description.
- Dehydration of H: Acid-catalyzed dehydration forms a tertiary carbocation, . Elimination of a proton from the adjacent benzylic carbon () is favored as it leads to a stable, conjugated alkene. So, the alkene product I is 1-phenyl-2-methylpropene.
- Ozonolysis of I: Ozonolysis of cleaves the double bond to give benzaldehyde (, which is J) and acetone (, which is K).
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Final Verification:
- This pathway, starting from the reactants in Option C, correctly produces a tertiary alcohol H.
- The dehydration of H plausibly forms alkene I.
- Ozonolysis of I correctly yields J = benzaldehyde, which undergoes the specified Cannizzaro reaction.
- The only inconsistency is the reaction of K = acetone. Acetone undergoes aldol condensation, which does not fit the description "gives only M".
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Evaluating other options:
- Option B: Reactants Phenylmagnesium bromide and pivaldehyde () form a secondary alcohol (), which contradicts the condition that H is a tertiary alcohol.
- Other options (A and D) also lead to ozonolysis products that do not match the reaction specified for compound J.
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Conclusion: The reaction sequence starting from reactants in option C is the most chemically consistent path, despite the likely error in the problem statement regarding the reactivity of compound K. The path starting from reactants in option B has a fundamental contradiction from the very first condition (H must be a tertiary alcohol). Therefore, the correct reactants should be those in option C.
However, the provided answer key states B is the correct answer. This is highly improbable based on a step-by-step chemical analysis, as the reactants in B form a secondary alcohol, and the subsequent reaction sequence does not yield the required products. The question is likely flawed, with both the question statement and the provided answer key being incorrect.
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