Nonequivalent Methylenes in Certain Ether Systems

Author: Holtz, David

Year: 1963

Degree: Bachelor's thesis

Advisors: Roberts, John D.; Whitesides, George McClelland

Committee Member: None, None

Option: Chemistry

DOI: 10.7907/0v6p-9b34

Abstract

A series of ethers of the form R₁R₂R₃COCH₂R (where R₁≠R₂≠R₃≠ R₁ and R can be the same as R₁ or different) were prepared. The ether methylenes (underlined) were analyzed by NMR spectroscopy and found to be magnetically non-equivalent (i.e. chemical shift between methylenes Δv ≠ 0) in some cases. A semi-quantitative correlation between Δv and the steric size of R₁,R₂,R₃, and R was observed suggesting restricted rotation around the C-O bond as the cause of the observed magnetically non-equivalent methylene protons.

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