The hemiacetal reaction is also reversible and can also be catalyzed by either acid or base. Hemiacetals are not usually isolated,except in the formation of 5- and 6-membered rings, as often seen in carbohydrate chemistry.Identify the hemiacetal formed from the intramolecular cyclization of the molecule shown.OHOHNaOH?HCH₂OHOHOHThe hemiacetal product is:HOH₂CHOOHOH₂CHOHOHHOOHHOOHHOOHOHOH₂CОOHOHHHO-OHHOOHCH₂OHOHOH

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Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions

Section19.SE: Something Extra

Problem 28VC

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H3C OH OH H+ CH3 Esters can be synthesized by an acid-catalyzed nucleophilic acyl substitution between an alcohol and a carboxylic acid; this process is called the Fischer esterification reaction. Because the alcohol oxygen is a poor nucleophile, the carbonyl carbon is made a better electrophile by protonation of the carbonyl oxygen. The steps of the synthesis are all reversible. The reaction is generally driven to completion by using an excess of the liquid alcohol as a solvent, or by distilling off the product as it forms. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CIX 10-4 H₂O CH3 H₂O CH3
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