1. (a) A cyclic sugar known as a furanose is shown below. This molecule is in equilibrium with an acyclic species. Provide the structure of the acyclic molecule and a detailed mechanism of its formation, using curved arrows. HO HO HO OH OH cat. H+ (b) Provide a product for the reaction below. Note that no water is lost or removed during this reaction. (The product is called a hemiketal rather than a hemiacetal since the reactant is a ketone rather than an aldehyde.) OH cat H+ A hemiketal OH OH OH (c) Provide a product for the reaction below. Note that water is removed during this reaction. OH HO cat. H+ in CH3OH O remove water HO OH OH

1. (a) A cyclic sugar known as a furanose is shown below. This molecule is in equilibrium with an acyclic species. Provide the structure of the acyclic molecule and a detailed mechanism of its formation, using curved arrows. HO HO HO OH OH cat. H+ (b) Provide a product for the reaction below. Note that no water is lost or removed during this reaction. (The product is called a hemiketal rather than a hemiacetal since the reactant is a ketone rather than an aldehyde.) OH cat H+ A hemiketal OH OH OH (c) Provide a product for the reaction below. Note that water is removed during this reaction. OH HO cat. H+ in CH3OH O remove water HO OH OH

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Concept explainers

Aldehydes and Ketones

Aldehydes and ketones are organic compounds that have a carbonyl group, C = O, as their functional group. They both differ in the placement of this carbonyl group in their structures.

Question

1. (a) A cyclic sugar known as a furanose is shown below. This
molecule is in equilibrium with an acyclic species. Provide the
structure of the acyclic molecule and a detailed mechanism of its
formation, using curved arrows.
HO
HO
HO
OH
cat. H+
OH
(b) Provide a product for the reaction below. Note that no water
is lost or removed during this reaction. (The product is called a
hemiketal rather than a hemiacetal since the reactant is a ketone
rather than an aldehyde.)
OH
cat H+
A hemiketal
OH
OH
OH
(c) Provide a product for the reaction below. Note that water is
removed during this reaction.
OH
HO
cat. H+ in CH3OH
O
remove water
HO
OH
OH

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