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Compound A (C,H12) absorbed 3 equivalents of H2 on catalytic reduction over a palladium catalyst to give hydrocarbon B (C,H19). Upon ozonolysis, compound A gave, among other things, a ketone that was identified as cyclohexanone. Upon treatment with an NaNH2 in liquid NH3 followed by addition of iodomethane, compound A gave a new hydrocarbon C (C10H14). What is the structure of starting Compound A? Compound C C10H14 1) NaNH,/NH3(/) 2) CH3I Compound A C9H12 H, (3 equiv.) Pd/C Compound B C9H18 1) O3 |2) Zn/ACOH, Н,0 other compounds cyclohexanone

Compound A (C,H12) absorbed 3 equivalents of H2 on catalytic reduction over a palladium catalyst to give hydrocarbon B (C,H19). Upon ozonolysis, compound A gave, among other things, a ketone that was identified as cyclohexanone. Upon treatment with an NaNH2 in liquid NH3 followed by addition of iodomethane, compound A gave a new hydrocarbon C (C10H14). What is the structure of starting Compound A? Compound C C10H14 1) NaNH,/NH3(/) 2) CH3I Compound A C9H12 H, (3 equiv.) Pd/C Compound B C9H18 1) O3 |2) Zn/ACOH, Н,0 other compounds cyclohexanone

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**Investigation of Compound A (C₉H₁₂):** Compound A, with the molecular formula C₉H₁₂, absorbed 3 equivalents of hydrogen (H₂) during catalytic reduction over a palladium catalyst, which resulted in the formation of hydrocarbon B (C₉H₁₈). Through ozonolysis, Compound A yielded, among other products, cyclohexanone as a ketone. This identification helped confirm the structure of the starting compound. **Transformation Analysis:** 1. **From Compound A to B:** - **Reaction Conditions:** H₂ with 3 equivalents over Pd/C catalyst - **Resulting Compound B:** C₉H₁₈ 2. **From Compound A to Cyclohexanone:** - **Reaction Conditions:** - 1.) Ozone (O₃) - 2.) Zinc/Acetic Acid, H₂O reduction - **Products:** Cyclohexanone + other compounds 3. **From A to Compound C (C₁₀H₁₄):** - **Reaction Steps:** - 1.) Sodium amide (NaNH₂) in liquid ammonia (NH₃) - 2.) Addition of methyl iodide (CH₃I) - **Resulting Compound C:** C₁₀H₁₄ **Structural Options for Compound A:** The diagram presents several possible structures for Compound A. The correct structure is determined by the reactions and products described: 1. A cyclohexane ring with alkyne side chain. 2. A cyclohexene ring with a butadiene side chain. 3. A cyclohexene ring with an allyl side chain. 4. A cyclohexene ring with a propynyl side chain. 5. A bicyclic compound with a double bond. Understand that these structural representations are pivotal in determining which one leads to the specific reactions and products observed. Engaging in these analyses allows chemists to elucidate the precise molecular arrangements and transformations within organic chemistry.
Transcribed Image Text:**Investigation of Compound A (C₉H₁₂):** Compound A, with the molecular formula C₉H₁₂, absorbed 3 equivalents of hydrogen (H₂) during catalytic reduction over a palladium catalyst, which resulted in the formation of hydrocarbon B (C₉H₁₈). Through ozonolysis, Compound A yielded, among other products, cyclohexanone as a ketone. This identification helped confirm the structure of the starting compound. **Transformation Analysis:** 1. **From Compound A to B:** - **Reaction Conditions:** H₂ with 3 equivalents over Pd/C catalyst - **Resulting Compound B:** C₉H₁₈ 2. **From Compound A to Cyclohexanone:** - **Reaction Conditions:** - 1.) Ozone (O₃) - 2.) Zinc/Acetic Acid, H₂O reduction - **Products:** Cyclohexanone + other compounds 3. **From A to Compound C (C₁₀H₁₄):** - **Reaction Steps:** - 1.) Sodium amide (NaNH₂) in liquid ammonia (NH₃) - 2.) Addition of methyl iodide (CH₃I) - **Resulting Compound C:** C₁₀H₁₄ **Structural Options for Compound A:** The diagram presents several possible structures for Compound A. The correct structure is determined by the reactions and products described: 1. A cyclohexane ring with alkyne side chain. 2. A cyclohexene ring with a butadiene side chain. 3. A cyclohexene ring with an allyl side chain. 4. A cyclohexene ring with a propynyl side chain. 5. A bicyclic compound with a double bond. Understand that these structural representations are pivotal in determining which one leads to the specific reactions and products observed. Engaging in these analyses allows chemists to elucidate the precise molecular arrangements and transformations within organic chemistry.
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