5-Hydroxyhexanal forms a six-membered cyclic hemiacetal, which predominates

Chapter 16, Problem 16.29

(choose chapter or problem)

5-Hydroxyhexanal forms a six-membered cyclic hemiacetal, which predominates atequilibrium 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 axialor equatorial. Also predict which of the alternative chair conformations for each ste-reoisomer is more stable.

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