H3C CH3CH₂ 14 Br Nat CN DMSO ?

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...
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What would be the major product of the following reaction?

**Chemical Reaction Description**

In this diagram, we observe a chemical reaction involving an organic molecule and a reagent. 

**Starting Material:**
The molecule depicted on the left is 2-bromo-2-methylbutane. It has a chiral center with the configuration:
- A bromine (Br) atom
- A hydrogen (H) atom
- A methyl group (CH₃)
- An ethyl group (CH₃CH₂)

**Reagent:**
- Sodium cyanide (Na⁺CN⁻)
- Solvent: Dimethyl sulfoxide (DMSO)

**Reaction Arrow:**
The arrow indicates that a chemical reaction is occurring. The question mark (?) signifies the unknown product of this reaction.

**Possible Reaction Analysis:**
Given the conditions (NaCN in DMSO), this setup suggests a nucleophilic substitution reaction, likely an SN2 mechanism due to the presence of a strong nucleophile (CN⁻) and polar aprotic solvent (DMSO). The CN⁻ ion would likely attack the carbon atom bonded to the bromine, leading to the substitution of the bromine atom with a cyano group (CN).

**Expected Outcome:**
The expected product would be 2-methyl-2-butanenitrile, with the configuration:
- CN group replacing the Br
- The attack should lead to an inversion of configuration at the chiral center.
Transcribed Image Text:**Chemical Reaction Description** In this diagram, we observe a chemical reaction involving an organic molecule and a reagent. **Starting Material:** The molecule depicted on the left is 2-bromo-2-methylbutane. It has a chiral center with the configuration: - A bromine (Br) atom - A hydrogen (H) atom - A methyl group (CH₃) - An ethyl group (CH₃CH₂) **Reagent:** - Sodium cyanide (Na⁺CN⁻) - Solvent: Dimethyl sulfoxide (DMSO) **Reaction Arrow:** The arrow indicates that a chemical reaction is occurring. The question mark (?) signifies the unknown product of this reaction. **Possible Reaction Analysis:** Given the conditions (NaCN in DMSO), this setup suggests a nucleophilic substitution reaction, likely an SN2 mechanism due to the presence of a strong nucleophile (CN⁻) and polar aprotic solvent (DMSO). The CN⁻ ion would likely attack the carbon atom bonded to the bromine, leading to the substitution of the bromine atom with a cyano group (CN). **Expected Outcome:** The expected product would be 2-methyl-2-butanenitrile, with the configuration: - CN group replacing the Br - The attack should lead to an inversion of configuration at the chiral center.
Expert Solution
Step 1: Introduction to the concept of SN2 reaction:

Here is the reaction in between alkyl halide and the nucleophile CN- (from NaCN), in presence of aprotic solvent DMSO.

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