Alcohols are acidic in nature. Therefore, a strong base canabstract the acidic hydrogen atom of the alcohol in a processknown as deprotonation. The alcohol forms an alkoxide ion bylosing the proton attached to the oxygen atom of the hydroxyl (-OH) group. The alkoxide formed can act as a base or anucleophile depending on the substrate and reaction conditions.However, not all bases can abstract the acidic proton of alcoholsand not all alcohols easily lose the proton. Deprotonationdepends on the strength of the base and the acidity of thealcohol. Strong bases, such as NaNH2, can easily abstract aproton from almost all alcohols. Likewise, more acidic alcoholslose 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)CH3CH,OH + NH3 →CH,CH,O-NHCH3CH3H3C-C-H+NH3 → H3 C-C-HOHO-NHCH3CH2OH + NaNH, → CH3CH,O-Na* + NH3CHC12Cl₂ HC-CH-OH+NaOH → Cl₂ HC-CH-O-Na+CHC12Submit+CH3CH3ⒸH3C-C-OH + NaOH → H₂C—C—O¯Na+ + H₂OCH3CH3Previous Answers

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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