(−)-Menthol is the most stable stereoisomer of 2-isopropyl-5-methylcyclohexanol and has the R configuration at the hydroxyl-substituted carbon. (a) Draw the preferred conformation of (−)-menthol. (b) (+)-Isomenthol has the same constitution as (−)-menthol. The configurations at C-1 and C-2 of (+)-isomenthol are the opposite of the corresponding chirality centers of (−)-menthol. Write the preferred conformation of (+)-isomenthol.

(−)-Menthol is the most stable stereoisomer of 2-isopropyl-5-methylcyclohexanol and has the R configuration at the hydroxyl-substituted carbon. (a) Draw the preferred conformation of (−)-menthol. (b) (+)-Isomenthol has the same constitution as (−)-menthol. The configurations at C-1 and C-2 of (+)-isomenthol are the opposite of the corresponding chirality centers of (−)-menthol. Write the preferred conformation of (+)-isomenthol.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter2: Alkanes And Cycloalkanes

Section: Chapter Questions

Problem 2.64P

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(A)Menthol, used to flavor various foods and tobacco, is the most stable stereoisomer of 2-isopropyl-5-methylcyclohexanol. Draw its most stable conformation. Is the hydroxyl group cis or trans to the isopropyl group? To the methyl group? (b) Neomenthol is a stereoisomer of menthol. That is, it has the same constitution but differs in the arrangement of its atoms in space. Neomenthol is the second most stable stereoisomer of 2-isopropyl-5methylcyclohexanol; it is less stable than menthol but more stable than any other stereoisomer. Write the structure of neomenthol in its most stable conformation.
8. Two structures of Lipitor (a drug used to lower cholesterol) are shown below. (a) Determine the absolute configuration of each indicated stereocenter. Fill in the correct circle. (b) Determine if the two structures are the same compound or stereoisomers. Fill in the correct circle. (a) НО. Carbon a HO O OH Carbon a: OR OS Carbon b H N Carbon b: R OS of H Carbon c: OR OS OH OH Carbon c F Carbon d: R OS OH Carbon d (b) The two structures are: O the same compound O stereoisomers
7) Draw bond-line formula (use solid and dash wedges to show proper stereochemistry) and a Fischer projection formula of (R)-6-bromo-1-hexen-3-ol.
(a) Draw all stereoisomers formed by monochlorination of the cis and trans isomers of 1,2-dimethylcyclobutane drawn below. (b) How many constitutional isomers are formed in each reaction? (c) Label any pairs of enantiomers formed.
(a) (R)-1,1,2-trimethylcyclohexane, label each structure you have drawn as chiral or achiral.
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Determine the configuration of each stereogenic center in the compound below. Highlight the carbon in red if the configuration is R, and in blue if the configuration is S. |||| OH OH D X 5 Ć
(v) Identify every chiral center in cholesterol (below) with an asterisk. HO (vi) Draw an energy vs. dihedral angle diagram that represents all the conformations of butane starting from the anti-conformation. (vii) Draw both chair conformations for the compound shown below using the templates provided. Circle the chair conformation that is lowest in energy. Br (viii) Draw a chair conformation that meets the following criteria. Axial chlorine at C5 Equatorial methyl at C4 Bromine on C2 that is cis to the chlorine 6 2 5 3 4
Q2 / Draw the following compounds so that they are optically active. A ) Br-CH2-CH2 -CH(CI)-CH(CI)-CH2-CH2-Br B) OH-CH2-CH(CH3)-CH2-CH(CH3)-CH2-OH B/ Draw the following compound in a chair position. RA
Be sure to answer all parts. Label each stereogenic center as R or S. CH3 CH(CH3)2 H HO C CH3 SH Stereocenter 1l:(select) Stereocenter 2: (select)
Dehydration of 1,2,2-trimethylcyclohexanol with H2SO4 affords 1-tertbutylcyclopentene as a minor product. (a) Draw a stepwise mechanism that shows how this alkene is formed. (b) Draw other alkenes formed in this dehydration. At least one must contain a five-membered ring.