Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Fill out the mechanism for the carbonyl condensation mechanism below. Be sure to use the necessary curved arrows and appropriate lone pairs to represent electron flow.
Transcribed Image Text:The image illustrates a complex chemical reaction mechanism, specifically involving the formation and transformation of organic compounds. Below is a detailed explanation of the process depicted:
1. **Initial Reactants**: The process begins with two reactants:
- A compound with a nitro group (NO₂) attached to a benzene ring along with other functional groups.
- A five-membered lactone ring containing a carbonyl (C=O) and hydroxy groups (OH).
2. **Formation of Key Intermediate**:
- The reactants combine to form an intermediate featuring a new bond between the original two molecules. This is indicated by the overall forward reaction arrow leading into a bracketed structure.
3. **Proton Transfers (P.T.)**:
- The next step is a proton transfer, indicated by the label "P.T. (no arrows)." Here, a proton is relocated within the molecule, facilitating further transformation.
4. **Water Elimination**:
- A dehydration step occurs, shown as "-H₂O," where water is removed from the molecule. This is followed by a reverse reaction arrow leading to an updated structure.
5. **Rearrangement Steps**:
- Further rearrangement occurs through additional proton transfers. Each structural change is bracketed, demonstrating an alteration in the molecular arrangement, maintaining stability throughout.
6. **Formation of Final Products**:
- The process culminates in the formation of two smaller organic products plus a hydronium ion (H₃O⁺).
- The first product retains a fragment resembling the original lactone.
- The second product is an aromatic compound reflecting transformation from the initial benzene-based reactant.
7. **Tautomerization**:
- The final sequence shows a conversion from a diketone form to its enol tautomer, denoted by "diketone to enol (no arrows)."
This detailed sequence exemplifies various reaction types, including condensation, rearrangement, and tautomerization, found in organic synthesis. The diagram emphasizes the importance of proton transfers and water elimination in driving the transformation forward.
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