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Chapter 10: Q46P (page 538)

Vinyl alcohols are generally unstable, quickly isomerizing to carbonyl compounds. Propose mechanisms for the following isomerizations.

(a)

(b)

c)

Short Answer

Expert verified

a)

b)

c)

Step by step solution

01

Vinyl alcohols

Vinyl alcohols are the simplest enols(CH2CHOH) , also named ethenol. They are unstable compounds and gets quickly isomerizes to carbonyl compounds.

02

Mechanism for the isomerizations in (a)

a) Here, H-A is a generic acid and A-1is the conjugate base. An aldehyde is formed along with H-A.


Mechanism of vinyl alcohol

03

Mechanism for the isomerizations in (b)

b) Here, H-A is a generic acid and A-1 is the conjugate base. A cyclohexanone is formed along with H-A.


The mechanism for the isomerization

04

Mechanism for the isomerizations in (c)

c) Here, the base attacks the cyclic alcohol. A cyclohexanone is formed along with -OH .


The mechanism for the isomerization

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