6. In an organic chemistry lab, chemists were attempting to convert compound I into compound II via a substitution reaction. To their surprise, compound II was the only obscrved compound after treating compound I with cyanide. :CEN : CN CI -CN II observed not observed a. Pruvide a detailed, stepwise mechanism for the transformation above that accounts livr the formation of pruduct II. Use the curved arIow lurmalism to show the tlow of electroLs. Show all lone pairs, intermediates, formul charges, und pertinent resonance structures.

Chemistry
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Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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**Educational Content for Organic Chemistry:**

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**Substitution Reaction in Organic Chemistry:**

In an organic chemistry lab, chemists were attempting to convert compound I into compound III via a substitution reaction. To their surprise, compound II was the only observed compound after treating compound I with cyanide.

**Diagram Explanation:**

- **Compound I**: This structure features a cyclopentane ring with a chlorine atom attached, depicted to the left in the diagram.
- **Reaction with Cyanide**: The reaction mechanism shows the addition of cyanide to compound I.
- **Compound II (Observed)**: The resulting structure features a cyclopentane ring where cyanide has replaced the chlorine atom, shown in the center of the diagram.
- **Compound III (Not Observed)**: The expected structure, not formed, features a similar ring with different structural arrangements after the substitution, shown in brackets to the right.

**Exercise:**

a. Provide a detailed, stepwise mechanism for the transformation above that accounts for the formation of product II. Use the curved arrow formalism to show the flow of electrons. Show all lone pairs, intermediates, formal charges, and pertinent resonance structures.

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This content introduces a classic substitution reaction mechanism, inviting further exploration of the electron flow and structural changes during the reaction process.
Transcribed Image Text:**Educational Content for Organic Chemistry:** --- **Substitution Reaction in Organic Chemistry:** In an organic chemistry lab, chemists were attempting to convert compound I into compound III via a substitution reaction. To their surprise, compound II was the only observed compound after treating compound I with cyanide. **Diagram Explanation:** - **Compound I**: This structure features a cyclopentane ring with a chlorine atom attached, depicted to the left in the diagram. - **Reaction with Cyanide**: The reaction mechanism shows the addition of cyanide to compound I. - **Compound II (Observed)**: The resulting structure features a cyclopentane ring where cyanide has replaced the chlorine atom, shown in the center of the diagram. - **Compound III (Not Observed)**: The expected structure, not formed, features a similar ring with different structural arrangements after the substitution, shown in brackets to the right. **Exercise:** a. Provide a detailed, stepwise mechanism for the transformation above that accounts for the formation of product II. Use the curved arrow formalism to show the flow of electrons. Show all lone pairs, intermediates, formal charges, and pertinent resonance structures. --- This content introduces a classic substitution reaction mechanism, inviting further exploration of the electron flow and structural changes during the reaction process.
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