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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Answered: The hemiacetal reaction is also…

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. H3C. CH3 nnc» XT :OH 2 CH₂OH HCI catalyst Aldehydes and ketones react reversibly with two equivalents of alcohol in the presence of an acid catalyst to give acetals. Alcohols are poor nucleophiles, and so protonation of the carbonyl oxygen is used to make the carbonyl carbon a stronger electrophile. Addition of the first equivalent of alcohol gives a hemiacetal, a hydroxyether. Addition of the second equivalent of alcohol is accompanied by loss of water to yield the product acetal. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CH3 H3C CH3OH H3CQ OCH3 CH3 H3C. H HO: :OCH 3 CH3 46
Give the product(s) for the following reaction, predicting the major product, anc indicating by which mechanism each is formed. Br MeOH heat

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