See Figure 11-5. The reaction shown would not happen as written because It would require the formation of a primary carbocation which is unstable. The proton would go on the primary carbon to make the secondary carbocation. The secondary carbocation that forms in the first mechanistic step would likely rearrange to form the more stable tertiary carbocation All of the above.

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**Question:**

See Figure 11-5. The reaction shown would not happen as written because:

1. ○ It would require the formation of a primary carbocation which is unstable.
2. ○ The proton would go on the primary carbon to make the secondary carbocation.
3. ○ The secondary carbocation that forms in the first mechanistic step would likely rearrange to form the more stable tertiary carbocation.
4. ○ All of the above.
Transcribed Image Text:**Question:** See Figure 11-5. The reaction shown would not happen as written because: 1. ○ It would require the formation of a primary carbocation which is unstable. 2. ○ The proton would go on the primary carbon to make the secondary carbocation. 3. ○ The secondary carbocation that forms in the first mechanistic step would likely rearrange to form the more stable tertiary carbocation. 4. ○ All of the above.
### Figure 11-5

The image illustrates the chemical reaction of a cyclopentene compound with HBr to produce a bromocyclopentane compound.

#### Reaction Pathways

A) **Stepwise Reaction:**
1. \( \text{Hg(OAc)}_2, \, \text{H}_2\text{O}, \, \text{H}^+ \)
2. \( \text{NaBH}_4 \)
3. \( \text{HBr} \)

B) **Hydroboration-Oxidation and Tosylation:**
1. \( \text{BH}_3 \)
2. \( \text{H}_2\text{O}_2, \, \text{OH}^-, \, \text{H}_2\text{O} \)
3. \( \text{TsCl} \)
4. \( \text{Br}^- \)

C) **Anti-Markovnikov Addition and Tosylation:**
1. \( \text{HBr} \)
2. \( \text{OH}^-, \, \text{DMF} \)
3. \( \text{TsCl} \)
4. \( \text{HBr} \)

D) **Oxymercuration-Demercuration and Halogenation:**
1. \( \text{Hg(OAc)}_2, \, \text{H}_2\text{O}, \, \text{H}^+ \)
2. \( \text{Br}_2, \, \text{H}_2\text{SO}_4 \)

The figure illustrates different reaction pathways to introduce bromine into a cyclopentane ring through various chemical transformations, including hydroboration, oxymercuration, and halogenation. Each step involves specific reagents that lead to the intermediate or final product formation.
Transcribed Image Text:### Figure 11-5 The image illustrates the chemical reaction of a cyclopentene compound with HBr to produce a bromocyclopentane compound. #### Reaction Pathways A) **Stepwise Reaction:** 1. \( \text{Hg(OAc)}_2, \, \text{H}_2\text{O}, \, \text{H}^+ \) 2. \( \text{NaBH}_4 \) 3. \( \text{HBr} \) B) **Hydroboration-Oxidation and Tosylation:** 1. \( \text{BH}_3 \) 2. \( \text{H}_2\text{O}_2, \, \text{OH}^-, \, \text{H}_2\text{O} \) 3. \( \text{TsCl} \) 4. \( \text{Br}^- \) C) **Anti-Markovnikov Addition and Tosylation:** 1. \( \text{HBr} \) 2. \( \text{OH}^-, \, \text{DMF} \) 3. \( \text{TsCl} \) 4. \( \text{HBr} \) D) **Oxymercuration-Demercuration and Halogenation:** 1. \( \text{Hg(OAc)}_2, \, \text{H}_2\text{O}, \, \text{H}^+ \) 2. \( \text{Br}_2, \, \text{H}_2\text{SO}_4 \) The figure illustrates different reaction pathways to introduce bromine into a cyclopentane ring through various chemical transformations, including hydroboration, oxymercuration, and halogenation. Each step involves specific reagents that lead to the intermediate or final product formation.
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