Icohols are acidic in nature. Therefore, a strong base can bstract the acidic hydrogen atom of the alcohol in a process nown as deprotonation. The alcohol forms an alkoxide ion by sing the proton attached to the oxygen atom of the hydroxyl ( OH) group. The alkoxide formed can act as a base or a ucleophile depending on the substrate and reaction conditions. owever, not all bases can abstract the acidic proton of alcohols nd not all alcohols easily lose the proton. Deprotonation epends on the strength of the base and the acidity of the cohol. Strong bases, such as NaNH₂, can easily abstract a roton from almost all alcohols. Likewise, more acidic alcohols se a proton more easily. Determine which of the following reactions would undergo deprotonation based on the strength of the base and the acidity of the alcohol. Check all that apply. ▸ View Available Hint(s) CH3CH₂OH + NH3 CH3CH₂O-NH- CH3 CH3 H3C-C-H+NH3 → H3C-C-H OH O-NH * CH3CH,OH + NaNH, → CH3CH,O-Na* + NH ✓ CHCL Cl₂ HC-CH-OH+NaOH → Cl₂ HC-CH-O-Na+ CHC12 CH3 CH3 H3C-C-OH + NaOH → H3C-C-O-Na+ + H₂O CH3 CH3
Icohols are acidic in nature. Therefore, a strong base can bstract the acidic hydrogen atom of the alcohol in a process nown as deprotonation. The alcohol forms an alkoxide ion by sing the proton attached to the oxygen atom of the hydroxyl ( OH) group. The alkoxide formed can act as a base or a ucleophile depending on the substrate and reaction conditions. owever, not all bases can abstract the acidic proton of alcohols nd not all alcohols easily lose the proton. Deprotonation epends on the strength of the base and the acidity of the cohol. Strong bases, such as NaNH₂, can easily abstract a roton from almost all alcohols. Likewise, more acidic alcohols se a proton more easily. Determine which of the following reactions would undergo deprotonation based on the strength of the base and the acidity of the alcohol. Check all that apply. ▸ View Available Hint(s) CH3CH₂OH + NH3 CH3CH₂O-NH- CH3 CH3 H3C-C-H+NH3 → H3C-C-H OH O-NH * CH3CH,OH + NaNH, → CH3CH,O-Na* + NH ✓ CHCL Cl₂ HC-CH-OH+NaOH → Cl₂ HC-CH-O-Na+ CHC12 CH3 CH3 H3C-C-OH + NaOH → H3C-C-O-Na+ + H₂O CH3 CH3
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter10: Alcohols
Section10.7: The Pinacol Rearrangement
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