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. OH OH NaOH ? H CH₂OH OH OH The hemiacetal product is: HOH₂C HO O HOH₂C H OH OH HO OH HO OH HO OH O HOH₂C О OH OH H HO- OH HO OH CH₂OH OH OH

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
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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.
OH
OH
NaOH
?
H
CH₂OH
OH
OH
The hemiacetal product is:
HOH₂C
HO
O
HOH₂C
H
OH
OH
HO
OH
HO
OH
HO
OH
O
HOH₂C
О
OH
OH
H
HO-
OH
HO
OH
CH₂OH
OH
OH
Transcribed Image Text: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. OH OH NaOH ? H CH₂OH OH OH The hemiacetal product is: HOH₂C HO O HOH₂C H OH OH HO OH HO OH HO OH O HOH₂C О OH OH H HO- OH HO OH CH₂OH OH OH
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