OH H+ - H a cyclic hemiacetal

Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter17: Aldehydes And Ketones
Section: Chapter Questions
Problem 17.47P: 17-47 What is the characteristic structural feature of a hemiacetal? Of an acetal?
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5-Hydroxyhexanal forms a six-membered cyclic hemiacetal, which predominates at equilibrium in aqueous solution.

(a) Draw a structural formula for this cyclic hemiacetal.

(b) How many stereoisomers are possible for 5-hydroxyhexanal?

(c) How many stereoisomers are possible for this cyclic hemiacetal?

(d) Draw alternative chair conformations for each stereoisomer and label groups axial or Also predict which of the alternative chair conformations for each stereoisomer is more stable.

OH
H+
- H
a cyclic hemiacetal
Transcribed Image Text:OH H+ - H a cyclic hemiacetal
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