Write the products of the following SN2 reaction: SN2 OCN + CH3B" Write the mechanism.

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
The image shows a chemical reaction equation involving an Sₙ2 reaction.

**Reaction:**

⊖CN + CH₃Br → (Sₙ2 reaction arrow) →

**Instruction:**

Write the products of the following Sₙ2 reaction.

**Task:**

Write the mechanism.

**Explanation:**

The reaction involves a cyanide ion (⊖CN) and methyl bromide (CH₃Br) undergoing an Sₙ2 reaction. In this bimolecular nucleophilic substitution reaction, the nucleophile (⊖CN) attacks the carbon atom in CH₃Br, displacing the bromide ion (Br⁻). This results in the formation of a new carbon-carbon bond, yielding acetonitrile (CH₃CN) and a bromide ion as products.

**Mechanism:**

1. The lone pair on the nitrogen atom of the cyanide ion attacks the carbon atom in methyl bromide from the opposite side of the Br group.
2. This attack forms a transition state where a bond between CN and the carbon is partially formed, while the bond between the carbon and bromine is partially broken.
3. The Br group leaves as the bromide ion (Br⁻), completing the formation of acetonitrile (CH₃CN).

Sₙ2 reactions typically proceed with inversion of configuration at the carbon center, due to the backside attack of the nucleophile.
Transcribed Image Text:The image shows a chemical reaction equation involving an Sₙ2 reaction. **Reaction:** ⊖CN + CH₃Br → (Sₙ2 reaction arrow) → **Instruction:** Write the products of the following Sₙ2 reaction. **Task:** Write the mechanism. **Explanation:** The reaction involves a cyanide ion (⊖CN) and methyl bromide (CH₃Br) undergoing an Sₙ2 reaction. In this bimolecular nucleophilic substitution reaction, the nucleophile (⊖CN) attacks the carbon atom in CH₃Br, displacing the bromide ion (Br⁻). This results in the formation of a new carbon-carbon bond, yielding acetonitrile (CH₃CN) and a bromide ion as products. **Mechanism:** 1. The lone pair on the nitrogen atom of the cyanide ion attacks the carbon atom in methyl bromide from the opposite side of the Br group. 2. This attack forms a transition state where a bond between CN and the carbon is partially formed, while the bond between the carbon and bromine is partially broken. 3. The Br group leaves as the bromide ion (Br⁻), completing the formation of acetonitrile (CH₃CN). Sₙ2 reactions typically proceed with inversion of configuration at the carbon center, due to the backside attack of the nucleophile.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 2 images

Blurred answer
Knowledge Booster
Catalysis and Enzymatic Reactions
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
  • SEE MORE 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