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Which of the following mechanisms is drawn correctly? Remember to check arrows, formal charges, stereochemistry, and intermediates (if any).

Which of the following mechanisms is drawn correctly? Remember to check arrows, formal charges, stereochemistry, and intermediates (if any).

Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter18: Aromaticity
Section: Chapter Questions
Problem 12E
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Please help me I am trying to study for an upcoming final and was confused on some of the practice problems.
**Question:** *Which of the following mechanisms is drawn correctly? Remember to check arrows, formal charges, stereochemistry, and intermediates (if any).* --- **Mechanism A:** In Mechanism A, the first diagram shows a molecule with a hydroxyl group (-OH) shown interacting with a carbanion intermediate. Specifically, the hydroxyl ion (-OH) arrows towards the hydrogen atom (H) connected to a carbonyl group (C=O), indicating a deprotonation step. The resulting product is depicted on the right, showing a structure where the hydroxyl ion (OH-) has left, and the carbonyl group has been reformed, with a phenyl (C6H5) ring, methyl group (Me), and carbonyl group (C=O) in a stable formation. --- **Mechanism B:** Image B represents a two-step mechanism. 1. The first step shows a structure where the hydroxyl group (OH) leaves, indicating elimination. The arrow directs from the bond between the hydroxyl group and the carbon, leading towards the oxygen, showing the formation of a water molecule. 2. The intermediate formed has a positive charge on the carbon adjacent to the former hydroxyl group shown by the arrow forming a double bond, leading to the final product which features a methyl group and reformed carbonyl group on a phenyl ring. --- **Mechanism C:** (Note: The image does not show Mechanism C and only lists diagrams for Mechanism A and Mechanism B.) --- **Explanation of Diagrams/Graphs:** - **Mechanism A Diagram:** - Left structure: A six-membered ring (phenyl) with a methyl group (Me), adjacent to a carbon bonded with a hydroxyl group and another carbonyl group. - Right structure: Similar to the left structure, but without the hydroxyl group, depicting the deprotonation step completion. - **Mechanism B Diagram:** - Left structure: A molecule with a hydroxyl group illustrated initially. - Intermediate: Shows a positively charged carbon and a departing water molecule, denoted by arrows indicating electron movement. - Right structure: Final product with the elimination of hydroxyl group oxygen, forming a new structure. This content explains the molecular mechanisms involved, providing visual chemical structures and the steps in the reaction, assisting educational understanding in organic chemistry.
Transcribed Image Text:**Question:** *Which of the following mechanisms is drawn correctly? Remember to check arrows, formal charges, stereochemistry, and intermediates (if any).* --- **Mechanism A:** In Mechanism A, the first diagram shows a molecule with a hydroxyl group (-OH) shown interacting with a carbanion intermediate. Specifically, the hydroxyl ion (-OH) arrows towards the hydrogen atom (H) connected to a carbonyl group (C=O), indicating a deprotonation step. The resulting product is depicted on the right, showing a structure where the hydroxyl ion (OH-) has left, and the carbonyl group has been reformed, with a phenyl (C6H5) ring, methyl group (Me), and carbonyl group (C=O) in a stable formation. --- **Mechanism B:** Image B represents a two-step mechanism. 1. The first step shows a structure where the hydroxyl group (OH) leaves, indicating elimination. The arrow directs from the bond between the hydroxyl group and the carbon, leading towards the oxygen, showing the formation of a water molecule. 2. The intermediate formed has a positive charge on the carbon adjacent to the former hydroxyl group shown by the arrow forming a double bond, leading to the final product which features a methyl group and reformed carbonyl group on a phenyl ring. --- **Mechanism C:** (Note: The image does not show Mechanism C and only lists diagrams for Mechanism A and Mechanism B.) --- **Explanation of Diagrams/Graphs:** - **Mechanism A Diagram:** - Left structure: A six-membered ring (phenyl) with a methyl group (Me), adjacent to a carbon bonded with a hydroxyl group and another carbonyl group. - Right structure: Similar to the left structure, but without the hydroxyl group, depicting the deprotonation step completion. - **Mechanism B Diagram:** - Left structure: A molecule with a hydroxyl group illustrated initially. - Intermediate: Shows a positively charged carbon and a departing water molecule, denoted by arrows indicating electron movement. - Right structure: Final product with the elimination of hydroxyl group oxygen, forming a new structure. This content explains the molecular mechanisms involved, providing visual chemical structures and the steps in the reaction, assisting educational understanding in organic chemistry.
### Chemical Reaction Pathways #### Reaction Pathway C: 1. **Initial Structure**: - The first molecule has a benzene ring attached to a complex structure that includes an oxygen bonded to a hydroxy group (OH), a methyl group (Me), and an ethylene bridge (CH₂). The structure features several curved arrows indicating electron movement in a reaction process. Specifically, an electron pair from the oxygen-hydroxy bond is moving to oxygen, making it negatively charged, and another arrow suggests breaking the ethylene bridge. 2. **Intermediate Structure**: - Following the defined electron movements, the intermediate structure is formed. Here, the benzene ring is still attached to the main complex, which now has a double-bonded oxygen (carbonyl group) and a separate hydroxy anion (OH⁻). 3. **Final Structure**: - The final product of this pathway is obtained after stabilization, forming a ketone. The benzene ring is now directly attached to a carbonyl (C=O) and a methyl group. A five-membered ring (cyclopentane) is also present, completing the structure. #### Reaction Pathway D: 1. **Initial Structure**: - Similar to Pathway C, the initial molecule in Pathway D starts with a benzene ring linked to a complex structure featuring a hydroxy group (OH), a methyl group (Me), and a hydroxide anion (OH⁻). Arrow symbols indicate electron pair movements, which will facilitate the reaction. 2. **Intermediate Structure**: - During the reaction, electrons shift as indicated by the curved arrows. The intermediate then forms, displaying a benzene ring with a ketone group (carbonyl group) and maintains an ethylene bridge but without the hydroxy group. 3. **Final Structure**: - The final product in Pathway D results in the benzene ring attached to a carbonyl group (C=O), a methyl group, and a five-membered ring (cyclopentane) maintaining the overall structure integrity but with a rearrangement. #### Multiple-Choice Question: - _Which of the Initially shown Reactions is represented by Options A, B, C, and D?_ - **O A.** - **O B.** - **O C.** - **O D.** This content provides a detailed step-by-step mechanism for chemical reactions illustrating molecular rearrangements
Transcribed Image Text:### Chemical Reaction Pathways #### Reaction Pathway C: 1. **Initial Structure**: - The first molecule has a benzene ring attached to a complex structure that includes an oxygen bonded to a hydroxy group (OH), a methyl group (Me), and an ethylene bridge (CH₂). The structure features several curved arrows indicating electron movement in a reaction process. Specifically, an electron pair from the oxygen-hydroxy bond is moving to oxygen, making it negatively charged, and another arrow suggests breaking the ethylene bridge. 2. **Intermediate Structure**: - Following the defined electron movements, the intermediate structure is formed. Here, the benzene ring is still attached to the main complex, which now has a double-bonded oxygen (carbonyl group) and a separate hydroxy anion (OH⁻). 3. **Final Structure**: - The final product of this pathway is obtained after stabilization, forming a ketone. The benzene ring is now directly attached to a carbonyl (C=O) and a methyl group. A five-membered ring (cyclopentane) is also present, completing the structure. #### Reaction Pathway D: 1. **Initial Structure**: - Similar to Pathway C, the initial molecule in Pathway D starts with a benzene ring linked to a complex structure featuring a hydroxy group (OH), a methyl group (Me), and a hydroxide anion (OH⁻). Arrow symbols indicate electron pair movements, which will facilitate the reaction. 2. **Intermediate Structure**: - During the reaction, electrons shift as indicated by the curved arrows. The intermediate then forms, displaying a benzene ring with a ketone group (carbonyl group) and maintains an ethylene bridge but without the hydroxy group. 3. **Final Structure**: - The final product in Pathway D results in the benzene ring attached to a carbonyl group (C=O), a methyl group, and a five-membered ring (cyclopentane) maintaining the overall structure integrity but with a rearrangement. #### Multiple-Choice Question: - _Which of the Initially shown Reactions is represented by Options A, B, C, and D?_ - **O A.** - **O B.** - **O C.** - **O D.** This content provides a detailed step-by-step mechanism for chemical reactions illustrating molecular rearrangements
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