Homework Help is Here – Start Your Trial Now!
Science
Chemistry
(A) The literature reports that when alcohol 1 (see structure below) is treated with thionyl chloride in diethyl ether, the single product is (35,5S)-3- chloro-5-methylcyclohexene (2) (no enantiomer of diastereomer of 2 is formed). Explain by writing a detailed mechanism. Look at the solution to LC-39 (B) Using a mechanism, predict what single stereoisomer of 2 should form when pyridine is substituted for the diethyl ether. (C) Finally, predict mechanistically what additional stereoisomers of 3- chloro-5-methylcyclohexene should form when 1 is treated with Lucas reagent (ZnCl₂/H₂0 CI).

(A) The literature reports that when alcohol 1 (see structure below) is treated with thionyl chloride in diethyl ether, the single product is (35,5S)-3- chloro-5-methylcyclohexene (2) (no enantiomer of diastereomer of 2 is formed). Explain by writing a detailed mechanism. Look at the solution to LC-39 (B) Using a mechanism, predict what single stereoisomer of 2 should form when pyridine is substituted for the diethyl ether. (C) Finally, predict mechanistically what additional stereoisomers of 3- chloro-5-methylcyclohexene should form when 1 is treated with Lucas reagent (ZnCl₂/H₂0 CI).

Chemistry
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...
See similar textbooks
icon
Related questions
Question

Can you make sure to include what the reactions follow SN1, SN2, SNi etc

1. (A) (B) (C) The literature reports that when alcohol 1 (see structure below) is treated with thionyl chloride in diethyl ether, the single product is (35,5S)-3- chloro-5-methylcyclohexene (2) (no enantiomer of diastereomer of 2 is formed). Explain by writing a detailed mechanism. Look at the solution to LC-39 Using a mechanism, predict what single stereoisomer of 2 should form when pyridine is substituted for the diethyl ether. Finally, predict mechanistically what additional stereoisomers of 3- chloro-5-methylcyclohexene should form when 1 is treated with Lucas reagent (ZnCl₂/H₂O*CI). CH3 OH H CH3 H 2
Transcribed Image Text:1. (A) (B) (C) The literature reports that when alcohol 1 (see structure below) is treated with thionyl chloride in diethyl ether, the single product is (35,5S)-3- chloro-5-methylcyclohexene (2) (no enantiomer of diastereomer of 2 is formed). Explain by writing a detailed mechanism. Look at the solution to LC-39 Using a mechanism, predict what single stereoisomer of 2 should form when pyridine is substituted for the diethyl ether. Finally, predict mechanistically what additional stereoisomers of 3- chloro-5-methylcyclohexene should form when 1 is treated with Lucas reagent (ZnCl₂/H₂O*CI). CH3 OH H CH3 H 2
Expert Solution
steps

Step by step

Solved in 4 steps with 3 images

SEE SOLUTIONCheck out a sample Q&A here
Blurred answer
Knowledge Booster
Organomagnesium Compounds
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
SEE MORE TEXTBOOKS