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

Transcribed Image Text:**Predict the product for the following reaction sequence:**
1) LiAlH₄
2) H₂O
3) TsCl, pyridine
**Given compound:**
The structure shows a cyclic compound with a five-membered ring attached to an aldehyde functional group (–CHO).
**Options:**
1. Cyclohexylmethyl alkene (double bond present)
2. Cyclohexylmethyl tosylate (with carbonyl group)
3. Cyclohexylmethyl alkene (double bond present)
4. Cyclohexylmethyl tosylate (with an –OTs group)
5. Cyclohexylmethyl tosylate (with an –OTs group)
**Explanation:**
1) **LiAlH₄:** This is a strong reducing agent commonly used to reduce aldehydes to primary alcohols. Thus, the aldehyde group (-CHO) will be reduced to a primary alcohol (-CH₂OH).
2) **H₂O:** Water is used during the workup phase to quench the reaction and neutralize the reaction mixture.
3) **TsCl, pyridine:** Tosyl chloride (TsCl) along with pyridine (a base) is used to convert alcohols into tosylates. Tosylation converts the -OH group into an -OTs group, making it a good leaving group.
**Final Product:**
The aldehyde is first reduced to produce a primary alcohol, and this alcohol is then converted into a tosylate group, yielding the final product as a cyclohexylmethyl tosylate (-OTs group).
Thus, the correct answer is most likely the fifth option, which shows the cyclohexylmethyl tosylate structure.
Expert Solution

This question has been solved!
Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.
Step by step
Solved in 2 steps with 2 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