Provide the systematic name of the major product after (S)-1-bromo-4-methylhexane reacts with sodium hydroxide in diethyl ether.

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:**

Provide the systematic name of the major product after (S)-1-bromo-4-methylhexane reacts with sodium hydroxide in diethyl ether.

---

**Explanation:**

When (S)-1-bromo-4-methylhexane reacts with sodium hydroxide (NaOH) in a solvent like diethyl ether, an S_N2 reaction mechanism typically occurs. In this mechanism, the bromine (Br) atom is replaced by a hydroxide ion (OH^-), yielding an alcohol. The stereochemistry inverts because of the backside attack characteristic of S_N2 reactions.

**Solution:**

Starting with (S)-1-bromo-4-methylhexane:
- The Br is at the 1-position.
- The methyl group is at the 4-position.

After the substitution reaction using NaOH:
- The Br group is replaced by an OH group.
- The stereochemistry inverts from (S) to (R) due to the S_N2 mechanism.

Thus, the major product of this reaction is (R)-1-hydroxy-4-methylhexane.

**Systematic Name:**

The systematic name of the major product is (R)-1-hydroxy-4-methylhexane.

---

This text outlines the chemical reaction process, explains the mechanism, and identifies the product's stereochemistry to assist students in understanding and identifying reaction outcomes in organic chemistry.
Transcribed Image Text:**Question:** Provide the systematic name of the major product after (S)-1-bromo-4-methylhexane reacts with sodium hydroxide in diethyl ether. --- **Explanation:** When (S)-1-bromo-4-methylhexane reacts with sodium hydroxide (NaOH) in a solvent like diethyl ether, an S_N2 reaction mechanism typically occurs. In this mechanism, the bromine (Br) atom is replaced by a hydroxide ion (OH^-), yielding an alcohol. The stereochemistry inverts because of the backside attack characteristic of S_N2 reactions. **Solution:** Starting with (S)-1-bromo-4-methylhexane: - The Br is at the 1-position. - The methyl group is at the 4-position. After the substitution reaction using NaOH: - The Br group is replaced by an OH group. - The stereochemistry inverts from (S) to (R) due to the S_N2 mechanism. Thus, the major product of this reaction is (R)-1-hydroxy-4-methylhexane. **Systematic Name:** The systematic name of the major product is (R)-1-hydroxy-4-methylhexane. --- This text outlines the chemical reaction process, explains the mechanism, and identifies the product's stereochemistry to assist students in understanding and identifying reaction outcomes in organic chemistry.
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
IR Spectroscopy of Organic Molecules
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