Chemistry
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ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Transcribed Image Text:**Topic: SN2 Reaction Mechanism**
Below is the SN2 reaction between chlorocyclohexane and cyanide (CN⁻). The task is to draw the missing curved arrow notation in the first box to reflect electron movements. In both boxes, you are required to add lone pairs of electrons and nonzero formal charges.
**Diagram Explanation:**
- **Left Box**:
- Reactants include chlorocyclohexane with a chlorine (Cl) atom attached to a cyclohexane ring, and a cyanide ion (CN⁻) depicted with a negative charge.
- The curved arrow needs to be drawn to indicate the nucleophilic attack by the cyanide ion on the cyclohexane carbon that is bonded to chlorine, demonstrating the electron movement.
- **Right Box**:
- Products show the cyanide ion now bonded to the cyclohexane ring, with chlorine (Cl⁻) having a negative charge as it leaves.
**Instructions:**
- Add the appropriate curved arrows to depict the electron shifts.
- Include lone pairs of electrons on relevant atoms.
- Denote nonzero formal charges where applicable.
Interactive tools and hints are available to aid in solving the problem. To continue with similar questions, proceed through the sequence.
Transcribed Image Text:This image contains a chemical structure along with a task prompt. The prompt says: "Add lone pairs of electrons and nonzero formal charges."
### Description of the Chemical Structure:
1. **Ring Structure:**
- The main feature is a six-membered carbon ring, which is a cyclohexane structure.
2. **Functional Groups:**
- Attached to one of the carbon atoms in the ring is a triple bond (alkyne) leading to a nitrogen atom, which is indicative of a nitrile group (C≡N).
3. **Chlorine Ion:**
- Nearby, there is a "Cl" symbol with a negative charge (Cl⁻), indicating the presence of a chloride ion.
### Explanation for Educational Context:
The structure outlines a cyclohexyl nitrile with a chloride counterion. When adding lone pairs of electrons and formal charges, consider:
- **Nitrogen in Nitrile Group:** Typically has one lone pair of electrons.
- **Chloride Ion (Cl⁻):** Should have three lone pairs of electrons as it is in a negatively charged state.
- **Carbon Atoms:** Usually do not carry lone pairs, but it's essential to show any necessary hydrogen atoms for full representation.
- **Formal Charges:** Check all atoms to ensure they have the correct number of valence electrons based on typical bonding patterns (e.g., carbon typically forms four bonds).
Adding these details accurately reflects a full understanding of structural representation for organic compounds.
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