raw the major product of this reaction. Ignore inorganic byproducts and the carboxylic acid side product. O 1. (CH3)2CuLi (excess) 2. H₂O

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
**Reaction Task:**

**Objective:** Draw the major product of the given reaction. Inorganic byproducts and the carboxylic acid side product should be ignored.

**Starting Material:**
- The structure shown is a symmetric compound known as benzil, featuring:
  - Two benzene rings attached to a central two-carbon chain.
  - Each carbon in the chain is doubly bonded to oxygen (carbonyl groups), forming two ketone groups.
  - The compound structure is: C₆H₅C(O)C(O)C₆H₅.

**Reaction Conditions:**
1. The first step involves the use of lithium dimethylcuprate, \((CH_3)_2CuLi\), in excess.
2. The second step involves the addition of water \((H_2O)\).

**Expected Major Product:** 
- In a typical reaction involving lithium diorganocopper reagents, a 1,4-addition to unsaturated carbonyl compounds may occur, leading to the addition of methyl groups. However, this compound does not have unsaturation compatible with 1,4-addition.
- Instead, a nucleophilic addition reaction at the ketone carbonyl groups is expected, likely resulting in the reduction of one or more of the ketone groups to secondary alcohol groups.

**Note:** The structure and exact nature of the final product are determined by the excess reagent and specifics of the reaction mechanism involved in organocopper chemistry.
Transcribed Image Text:**Reaction Task:** **Objective:** Draw the major product of the given reaction. Inorganic byproducts and the carboxylic acid side product should be ignored. **Starting Material:** - The structure shown is a symmetric compound known as benzil, featuring: - Two benzene rings attached to a central two-carbon chain. - Each carbon in the chain is doubly bonded to oxygen (carbonyl groups), forming two ketone groups. - The compound structure is: C₆H₅C(O)C(O)C₆H₅. **Reaction Conditions:** 1. The first step involves the use of lithium dimethylcuprate, \((CH_3)_2CuLi\), in excess. 2. The second step involves the addition of water \((H_2O)\). **Expected Major Product:** - In a typical reaction involving lithium diorganocopper reagents, a 1,4-addition to unsaturated carbonyl compounds may occur, leading to the addition of methyl groups. However, this compound does not have unsaturation compatible with 1,4-addition. - Instead, a nucleophilic addition reaction at the ketone carbonyl groups is expected, likely resulting in the reduction of one or more of the ketone groups to secondary alcohol groups. **Note:** The structure and exact nature of the final product are determined by the excess reagent and specifics of the reaction mechanism involved in organocopper chemistry.
Expert Solution
Step 1: Interpretation of given problem

Given is organic reaction. 

The reactant is acid anhydride. 

Reagent Gilman reagent.

steps

Step by step

Solved in 3 steps with 2 images

Blurred answer
Knowledge Booster
Reactive Intermediates
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