University Chemistry ›› 2015, Vol. 30 ›› Issue (1): 68-71.doi: 10.3866/PKU.DXHX20150114

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The Acidity Sequence of Alcohols in Vapor Phase in Terms of No-bond Resonance

Wang Wenfeng, Yuan Yaofeng   

  1. College of Chemistry, Fuzhou University, Fuzhou 350108, Fujian, China
  • Published:2015-02-25


By comparing bond energies of C—O single bond and C=O double bond, it can be predicted that the conjugate bases of alcohols are able to form C=O double bond via no-bond resonance. Since the bond energy of C—C single bond is much lower than that of the C—H single bond, methyl group is easier to stabilize alkoxide ions via no-bond resonance compared with H atom, the acidity sequence of alcohols in vapor phase is: (CH3)3COH >(CH3)2CHOH >CH3CH2OH >CH3OH. This viewpoint has been supported by the result of quantum chemistry calculation.

Key words: Bond energy, No-bond resonance, Alcohol, Acidity sequence