Acetyl chloride, CH3COCl, reacts with the hydroxyl groupsof alcohols to form ester groups with the elimination ofHCl. When an unknown compound X with formulaC4H8O3 reacted with acetyl chloride, a new compound Ywith formula C8H12O5 was formed.(a) How many hydroxyl groups were there in X?(b) Assume that X is an aldehyde. Write a possible structure for X and a                 possible structure for Y consistent     with your structure for X.

Chemistry: Principles and Practice
3rd Edition
ISBN:9780534420123
Author:Daniel L. Reger, Scott R. Goode, David W. Ball, Edward Mercer
Publisher:Daniel L. Reger, Scott R. Goode, David W. Ball, Edward Mercer
Chapter22: Organic Chemistry And Biochemistry
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Problem 88QE
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Acetyl chloride, CH3COCl, reacts with the hydroxyl groups
of alcohols to form ester groups with the elimination of
HCl. When an unknown compound X with formula
C4H8O3 reacted with acetyl chloride, a new compound Y
with formula C8H12O5 was formed.
(a) How many hydroxyl groups were there in X?
(b) Assume that X is an aldehyde. Write a possible structure for X and a                 possible structure for Y consistent
     with your structure for X.

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