
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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Transcribed Image Text:**Question:**
Which of the following nucleophiles is most reactive in \( S_N2 \) reactions?
**Structures:**
- **I.** \( \text{C}_2\text{H}_5\text{NH}_2 \)
- **II.** \( \text{C}_2\text{H}_5\text{NH}^- \)
- **III.** \( \text{C}_6\text{H}_5\text{NH}_2 \)
**Options:**
- A. I
- B. II
- C. III
- D. All the nucleophiles are equally reactive.

Transcribed Image Text:**Question:**
Examine the alkyl bromides below. Which is the most reactive as a substrate in \(S_N2\) reactions with \( I^- \) (acetone solvent)?
**Structures:**
- **Structure I**: Tertiary butyl bromide (2-bromo-2-methylpropane)
- **Structure II**: 1-bromobutane
- **Structure III**: 1-bromopropane
- **Structure IV**: Methyl bromide
**Select one:**
- A. IV
- B. I
- C. II
- D. III
- E. All are equally reactive
**Description of the Structures:**
1. **Structure I** is a tertiary alkyl bromide with the bromine atom bonded to a carbon that is connected to three other carbon atoms.
2. **Structure II** is a primary alkyl bromide where the bromine is bonded to a carbon connected to one other carbon atom and two hydrogen atoms.
3. **Structure III** is similar to Structure II but with a shorter chain.
4. **Structure IV** is a methyl bromide with the bromine atom bonded directly to a methyl group (CH\(_3\)).
**Explanation:**
In \(S_N2\) reactions, the reactivity is highest for primary halides and lowest for tertiary halides. This makes Structure IV (methyl bromide) the most reactive option due to its minimal steric hindrance, allowing for faster nucleophilic attack.
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