b. Out of the four isomers shown above (menthol, isomenthol, neomenthol, and neoisomenthol), which isomer do you predict is the most stable? It may help to draw out each isomer in its most stable chair conformer to determine which has the most equatorial groups.

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Chapter1: Chemical Foundations
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8. EXTRA PRACTICE: Menthol is a naturally occurring molecule found in the peppermint plant. Other
possible stereoisomers of menthol include isomenthol, neomenthol, and neoisomenthol.
܀ ܀ ܀ ܀
QH
menthol
oH
isomenthol
QH
neomenthol
*OH
neoisomenthol
a. Menthol has two possible chair conformers. Draw both conformers and predict which one is more
stable.
b. Out of the four isomers shown above (menthol, isomenthol, neomenthol, and neoisomenthol), which
isomer do you predict is the most stable? It may help to draw out each isomer in its most stable chair
conformer to determine which has the most equatorial groups.
Transcribed Image Text:8. EXTRA PRACTICE: Menthol is a naturally occurring molecule found in the peppermint plant. Other possible stereoisomers of menthol include isomenthol, neomenthol, and neoisomenthol. ܀ ܀ ܀ ܀ QH menthol oH isomenthol QH neomenthol *OH neoisomenthol a. Menthol has two possible chair conformers. Draw both conformers and predict which one is more stable. b. Out of the four isomers shown above (menthol, isomenthol, neomenthol, and neoisomenthol), which isomer do you predict is the most stable? It may help to draw out each isomer in its most stable chair conformer to determine which has the most equatorial groups.
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