9.53 Rank the following substrates in order from slowest SN2 reaction rate to fastest. Br Br H3C Br Br A В D

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**Problem 9.53**

Rank the following substrates in order from slowest \( S_N2 \) reaction rate to fastest.

**Substrates:**

- **A:** 2-Bromo-2-methylpropane
- **B:** 1-Bromo-2-butene
- **C:** 3-Bromo-1-butene
- **D:** 4-Bromo-1-butene

### Explanation:

The image shows four different organic molecules labeled A, B, C, and D, each containing a bromine (Br) atom. The task requires ranking these substrates according to their susceptibility to an \( S_N2 \) (bimolecular nucleophilic substitution) reaction, from the slowest to the fastest.

### Structural Details:

- **A** is a branched alkane, which typically hinders \( S_N2 \) reactions due to steric factors.
- **B, C,** and **D** are butene derivatives, with the location of the bromine atom varying. These are more linear, allowing easier nucleophilic attack.

Factors such as steric hindrance and the position of substituents play crucial roles in determining the rate of \( S_N2 \) reactions. Linear or less hindered substrates generally exhibit faster reaction rates. As a result, one can anticipate that:

- **A** will likely display the slowest reaction rate due to significant steric hindrance.
- **D** is likely to have the fastest rate due to the least steric hindrance, given its primary position and linear structure.

The list is likely ordered from slowest to fastest: A, B, C, D.
Transcribed Image Text:**Problem 9.53** Rank the following substrates in order from slowest \( S_N2 \) reaction rate to fastest. **Substrates:** - **A:** 2-Bromo-2-methylpropane - **B:** 1-Bromo-2-butene - **C:** 3-Bromo-1-butene - **D:** 4-Bromo-1-butene ### Explanation: The image shows four different organic molecules labeled A, B, C, and D, each containing a bromine (Br) atom. The task requires ranking these substrates according to their susceptibility to an \( S_N2 \) (bimolecular nucleophilic substitution) reaction, from the slowest to the fastest. ### Structural Details: - **A** is a branched alkane, which typically hinders \( S_N2 \) reactions due to steric factors. - **B, C,** and **D** are butene derivatives, with the location of the bromine atom varying. These are more linear, allowing easier nucleophilic attack. Factors such as steric hindrance and the position of substituents play crucial roles in determining the rate of \( S_N2 \) reactions. Linear or less hindered substrates generally exhibit faster reaction rates. As a result, one can anticipate that: - **A** will likely display the slowest reaction rate due to significant steric hindrance. - **D** is likely to have the fastest rate due to the least steric hindrance, given its primary position and linear structure. The list is likely ordered from slowest to fastest: A, B, C, D.
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