Which of the following nucleophiles is most reactive in SN2 reactions? I. II. NH, NH II NH- Select one: А. I B. II C. II D. All the nucleophiles are equally reactive.

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
icon
Related questions
icon
Concept explainers
Question
**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:** 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.
**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.
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.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 1 images

Blurred answer
Knowledge Booster
Aromatic Compounds
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY