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CHM 7200 Organic Structures and Mechanisms Fall Term 2005 Problem Set 1: This problem set is now available at (www.blackboard.wayne.edu). It will be due in
 

Summary: CHM 7200 Organic Structures and Mechanisms Fall Term 2005
Problem Set 1: This problem set is now available at (www.blackboard.wayne.edu). It will be due in
class 7 days (09/16/05) from today (09/09/05). Grades will be administered as follows: 5 (exceptional
effort), 4 (complete), 3 (incomplete or inadequate effort), 2 (poor effort), 0 (nonexistent). No late problem
sets will be accepted.
1. Problem: Consider the structures XCH2OH where X = OCH3 and F. What is the most
favorable conformation of each molecule? Illustrate the dihedral angle relationship along the CO
bond. Why is it the most favorable conformation? Explain using FMO principles learned in class.
Answer:
Fluoromethanol F-CH2OH
Methoxymethanol MeO-CH2OH
The most favorable conformation of the molecules listed above can be accounted for by the anomeric
effect. In the case of fluoromethanol, where an oxygen lon-pair is anti to fluorine, the conformation
having the hydroxyl hydrogen GAUCHE to the fluorine is preferred.
H O
F
H
H
Gauche
H O

  

Source: Andreana, Peter R. - Department of Chemistry, Wayne State University

 

Collections: Chemistry