Curved arrows are used to illustrate the flow of electrons. Using the provided starting structure, draw the curved electron-pushing arrows for the following reaction or mechanistic step(s). Be sure to account for all bond-breaking and bond-making steps. Then draw the organic product of this reaction. Include all lone pairs in the structures. Ignore inorganic byproducts and counterions. NECO CI Select to Add Arrows NaCN Na Ⓒ THF

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Chapter1: Chemical Foundations
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**Problem 5 of 44**

Curved arrows are used to illustrate the flow of electrons. Using the provided starting structure, draw the curved electron-pushing arrows for the following reaction or mechanistic step(s).

Be sure to account for all bond-breaking and bond-making steps. Then draw the organic product of this reaction.

Include all lone pairs in the structures. Ignore inorganic byproducts and counterions.

---

**Diagram Description:**

- The initial structure shows a carbon chain with a chlorine atom (Cl) attached. 
- There is also a cyano group (C≡N) shown, likely as part of a sodium cyanide (Na⁺ CN⁻) reagent. 
- The setup indicates that a nucleophilic substitution reaction is likely taking place.

**Reaction:**

The reaction involves sodium cyanide (NaCN) in tetrahydrofuran (THF) as a solvent. The CN⁻ ion functions as the nucleophile, attacking the carbon that bears the chlorine, which is the leaving group.

**Instructions:**

1. Use curved arrows to indicate the movement of electrons.
2. Show all lone pairs on atoms.
3. Ignore any inorganic byproducts (like NaCl) and counterions.

(End of Diagram Description)
Transcribed Image Text:**Problem 5 of 44** Curved arrows are used to illustrate the flow of electrons. Using the provided starting structure, draw the curved electron-pushing arrows for the following reaction or mechanistic step(s). Be sure to account for all bond-breaking and bond-making steps. Then draw the organic product of this reaction. Include all lone pairs in the structures. Ignore inorganic byproducts and counterions. --- **Diagram Description:** - The initial structure shows a carbon chain with a chlorine atom (Cl) attached. - There is also a cyano group (C≡N) shown, likely as part of a sodium cyanide (Na⁺ CN⁻) reagent. - The setup indicates that a nucleophilic substitution reaction is likely taking place. **Reaction:** The reaction involves sodium cyanide (NaCN) in tetrahydrofuran (THF) as a solvent. The CN⁻ ion functions as the nucleophile, attacking the carbon that bears the chlorine, which is the leaving group. **Instructions:** 1. Use curved arrows to indicate the movement of electrons. 2. Show all lone pairs on atoms. 3. Ignore any inorganic byproducts (like NaCl) and counterions. (End of Diagram Description)
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