8.30 Draw the complete, detailed mechanism (including curved arrows) for each of the following reactions occurring via (a) an SN2 mechanism and (b) an Sy1 mechanism. Pay attention to stereochemistry. (1) Br (i) NaOH NaOH Problems / 457

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Chapter1: Chemical Foundations
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**Exercise 8.30**

**Objective:** Draw the complete, detailed mechanism, including curved arrows, for each of the following reactions occurring via (a) an S<sub>N</sub>2 mechanism and (b) an S<sub>N</sub>1 mechanism. Pay attention to stereochemistry.

---

**(i)** 

**Reactants:** A cyclohexane ring with a bromine (Br) substituent.

- **Reagents:** NaOH

- **Reaction:** ?

---

**(ii)** 

**Reactants:** A cyclohexane ring with an iodine (I) substituent, showing a wedge bond indicating stereochemistry. There is also a methyl (CH<sub>3</sub>) group on the cyclohexane in the back.

- **Reagents:** NaOH 

- **Reaction:** ?

---

**(iii)** 

**Reactants:** A cyclohexane ring with an iodine (I) substituent, depicted with a dashed bond, indicating stereochemistry. Also includes a methyl (CH<sub>3</sub>) group in the front.

- **Reagents:** NaOH

- **Reaction:** ?

---

**(iv)** 

**Reactants:** A cyclohexane ring with an iodine (I) and a methyl (CH<sub>3</sub>) substituent, both depicted with wedge bonds, indicating stereochemistry.

- **Reagents:** KBr

- **Reaction:** ?

---

**Page Reference:** Problems / 457

**Instructions:** Consider the stereochemistry when proposing mechanism pathways.
Transcribed Image Text:**Exercise 8.30** **Objective:** Draw the complete, detailed mechanism, including curved arrows, for each of the following reactions occurring via (a) an S<sub>N</sub>2 mechanism and (b) an S<sub>N</sub>1 mechanism. Pay attention to stereochemistry. --- **(i)** **Reactants:** A cyclohexane ring with a bromine (Br) substituent. - **Reagents:** NaOH - **Reaction:** ? --- **(ii)** **Reactants:** A cyclohexane ring with an iodine (I) substituent, showing a wedge bond indicating stereochemistry. There is also a methyl (CH<sub>3</sub>) group on the cyclohexane in the back. - **Reagents:** NaOH - **Reaction:** ? --- **(iii)** **Reactants:** A cyclohexane ring with an iodine (I) substituent, depicted with a dashed bond, indicating stereochemistry. Also includes a methyl (CH<sub>3</sub>) group in the front. - **Reagents:** NaOH - **Reaction:** ? --- **(iv)** **Reactants:** A cyclohexane ring with an iodine (I) and a methyl (CH<sub>3</sub>) substituent, both depicted with wedge bonds, indicating stereochemistry. - **Reagents:** KBr - **Reaction:** ? --- **Page Reference:** Problems / 457 **Instructions:** Consider the stereochemistry when proposing mechanism pathways.
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