Which of the following sequences would successfully accomplish the transformation shown below? (A) (B) (C) (D) H₂ Lindlar's cat. 1) BuLi 2) Mel H₂ Lindlar's cat. 1) BuLi 2) Mel 1) 03 2) Me₂S HgSO4 H₂SO4, H₂O H₂O [H₂SO4] 1) 03 2) Me₂S
Which of the following sequences would successfully accomplish the transformation shown below? (A) (B) (C) (D) H₂ Lindlar's cat. 1) BuLi 2) Mel H₂ Lindlar's cat. 1) BuLi 2) Mel 1) 03 2) Me₂S HgSO4 H₂SO4, H₂O H₂O [H₂SO4] 1) 03 2) Me₂S
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...
Related questions
Question
![**Question:**
Which of the following sequences would successfully accomplish the transformation shown below?
**Diagram:**
The initial structure is a terminal alkyne with a triple bond. The target structure is a ketone with a propyl group attached to the carbonyl carbon.
**Reaction Sequences:**
(A)
1. \( \text{H}_2 \) with Lindlar's catalyst ➔ partial hydrogenation to a cis-alkene
2. \( \text{O}_3 \), \( \text{Me}_2\text{S} \) ➔ ozonolysis and reduction to form aldehydes or ketones
(B)
1. \( \text{BuLi} \) ➔ strong base, often used for deprotonation
2. \( \text{MeI} \) ➔ alkylation with methyl iodide
3. \( \text{HgSO}_4 \), \( \text{H}_2\text{SO}_4 \), \( \text{H}_2\text{O} \) ➔ hydration of alkynes to form ketones
(C)
1. \( \text{H}_2 \) with Lindlar's catalyst ➔ partial hydrogenation to a cis-alkene
2. \( \text{H}_2\text{O} \), \([ \text{H}_2\text{SO}_4 ] \) ➔ hydration to form alcohols or ketones
(D)
1. \( \text{BuLi} \) ➔ strong base, often used for deprotonation
2. \( \text{MeI} \) ➔ alkylation with methyl iodide
3. \( \text{O}_3 \), \( \text{Me}_2\text{S} \) ➔ ozonolysis and reduction to form aldehydes or ketones
**Answer:**
The correct sequence is **(B)**: Using \( \text{HgSO}_4 \), \( \text{H}_2\text{SO}_4 \), \( \text{H}_2\text{O} \) with an alkyne will lead to the formation of a ketone through the hydration of the alkyne.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F28000c02-e2c6-4a8b-b2f9-904011bfd87b%2Fb1ac72e1-28fb-4612-ba01-3e903ec02217%2Fpuis14g_processed.png&w=3840&q=75)
Transcribed Image Text:**Question:**
Which of the following sequences would successfully accomplish the transformation shown below?
**Diagram:**
The initial structure is a terminal alkyne with a triple bond. The target structure is a ketone with a propyl group attached to the carbonyl carbon.
**Reaction Sequences:**
(A)
1. \( \text{H}_2 \) with Lindlar's catalyst ➔ partial hydrogenation to a cis-alkene
2. \( \text{O}_3 \), \( \text{Me}_2\text{S} \) ➔ ozonolysis and reduction to form aldehydes or ketones
(B)
1. \( \text{BuLi} \) ➔ strong base, often used for deprotonation
2. \( \text{MeI} \) ➔ alkylation with methyl iodide
3. \( \text{HgSO}_4 \), \( \text{H}_2\text{SO}_4 \), \( \text{H}_2\text{O} \) ➔ hydration of alkynes to form ketones
(C)
1. \( \text{H}_2 \) with Lindlar's catalyst ➔ partial hydrogenation to a cis-alkene
2. \( \text{H}_2\text{O} \), \([ \text{H}_2\text{SO}_4 ] \) ➔ hydration to form alcohols or ketones
(D)
1. \( \text{BuLi} \) ➔ strong base, often used for deprotonation
2. \( \text{MeI} \) ➔ alkylation with methyl iodide
3. \( \text{O}_3 \), \( \text{Me}_2\text{S} \) ➔ ozonolysis and reduction to form aldehydes or ketones
**Answer:**
The correct sequence is **(B)**: Using \( \text{HgSO}_4 \), \( \text{H}_2\text{SO}_4 \), \( \text{H}_2\text{O} \) with an alkyne will lead to the formation of a ketone through the hydration of the alkyne.
Expert Solution
This question has been solved!
Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.
This is a popular solution!
Trending now
This is a popular solution!
Step by step
Solved in 3 steps with 1 images
Knowledge Booster
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
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY