16) What is the product of the following reaction? A) (1) (2) H30 ОН B) OH OH -ов об c) OH D)

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 16:**

What is the product of the following reaction?

**Reaction:**

The given reaction involves two steps:

1. The starting compound is a benzaldehyde derivative with a ketone group (C=O) attached to a phenyl group. It is treated with cyclohexyl lithium (cyclohexane ring attached to lithium).
   
2. The intermediate product is then treated with hydronium ion (\( \text{H}_3\text{O}^+ \)).

**Options:**

The possible products are designated as A, B, C, and D, each representing different structural isomers formed from the reaction.

- **A):** The phenyl group is attached to a secondary alcohol group, with the cyclohexane ring adjacent to the ketone origin.
  
- **B):** The structure shows the phenyl group attached to a primary alcohol group, with the cyclohexane ring at the end of the new chain.
  
- **C):** Similar to A, the structure contains a secondary alcohol with phenyl adjacent to the ketone origin but differs in orientation.
  
- **D):** The structure results in a secondary alcohol, with the phenyl group positioned between cyclohexane and the hydroxyl group.

These structures represent different stereochemical outcomes of the reaction. The correct answer should be determined based on the mechanism of organolithium addition to the carbonyl group and subsequent reaction with water.
Transcribed Image Text:**Question 16:** What is the product of the following reaction? **Reaction:** The given reaction involves two steps: 1. The starting compound is a benzaldehyde derivative with a ketone group (C=O) attached to a phenyl group. It is treated with cyclohexyl lithium (cyclohexane ring attached to lithium). 2. The intermediate product is then treated with hydronium ion (\( \text{H}_3\text{O}^+ \)). **Options:** The possible products are designated as A, B, C, and D, each representing different structural isomers formed from the reaction. - **A):** The phenyl group is attached to a secondary alcohol group, with the cyclohexane ring adjacent to the ketone origin. - **B):** The structure shows the phenyl group attached to a primary alcohol group, with the cyclohexane ring at the end of the new chain. - **C):** Similar to A, the structure contains a secondary alcohol with phenyl adjacent to the ketone origin but differs in orientation. - **D):** The structure results in a secondary alcohol, with the phenyl group positioned between cyclohexane and the hydroxyl group. These structures represent different stereochemical outcomes of the reaction. The correct answer should be determined based on the mechanism of organolithium addition to the carbonyl group and subsequent reaction with water.
Expert Solution
Step 1

Organolithium compound react carbonyl compound and produce alcohol 

steps

Step by step

Solved in 2 steps with 1 images

Blurred answer
Knowledge Booster
Ionic Equilibrium
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.
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