Assuming that each of the following alkyl bromides undergoes an SN1 reaction, which substrate's carbocation intermediate is most likely to undergoes a rearrangement? (......Hint: Remember that a 1,2-shift can involve a shift of -H or -R). ||| Br Br || IV Br Br

Chemistry for Today: General, Organic, and Biochemistry
9th Edition
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Chapter14: Aldehydes And Ketones
Section: Chapter Questions
Problem 14.55E: The addition of water to aldehydes and ketones occurs rapidly, although it is not thermodynamically...
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**Question:**

Assuming that each of the following alkyl bromides undergoes an Sₙ1 reaction, which substrate's carbocation intermediate is most likely to undergo a rearrangement? *(Hint: Remember that a 1,2-shift can involve a shift of -H or -R.)*

**Diagrams of Alkyl Bromides:**

- **Structure I:** A linear chain with a bromine (Br) attached to the second carbon.
- **Structure II:** A cyclohexane ring with a bromine (Br) attached to one of the carbons.
- **Structure III:** A branched chain with a bromine (Br) attached to a carbon that is connected to a methyl group.
- **Structure IV:** A tertiary structure with a bromine (Br) attached to a carbon with two methyl groups.

**Options:**
- **A.** II
- **B.** III
- **C.** IV
- **D.** I

The question prompts the reader to identify which alkyl bromide structure would likely undergo a rearrangement during an Sₙ1 reaction. The hint suggests considering a 1,2-shift, where a hydrogen or an alkyl group migrates to stabilize the carbocation intermediate.
Transcribed Image Text:**Question:** Assuming that each of the following alkyl bromides undergoes an Sₙ1 reaction, which substrate's carbocation intermediate is most likely to undergo a rearrangement? *(Hint: Remember that a 1,2-shift can involve a shift of -H or -R.)* **Diagrams of Alkyl Bromides:** - **Structure I:** A linear chain with a bromine (Br) attached to the second carbon. - **Structure II:** A cyclohexane ring with a bromine (Br) attached to one of the carbons. - **Structure III:** A branched chain with a bromine (Br) attached to a carbon that is connected to a methyl group. - **Structure IV:** A tertiary structure with a bromine (Br) attached to a carbon with two methyl groups. **Options:** - **A.** II - **B.** III - **C.** IV - **D.** I The question prompts the reader to identify which alkyl bromide structure would likely undergo a rearrangement during an Sₙ1 reaction. The hint suggests considering a 1,2-shift, where a hydrogen or an alkyl group migrates to stabilize the carbocation intermediate.
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