stereoisomer (isomenthol), and the
1S,2S,5R
stereoisomer (neomenthol).
OH
b. Of the stereoisomers described above, natural menthol ([
α
]
D
= –51) and neomenthol ([
α
]
D
= +21) are the major
constituents in mentha oil, their main natural source.
The menthol-neomenthol mixture in a natural sample of mentha oil
exhibits ([
α
]
D
= –33).
What are the percentages of natural menthol and neomenthol in this oil?
menthol
9. Draw 4 structural isomers of molecular formula C
4
H
7
Cl that each have a configurational stereoisomer.
Provide the
structure of the stereoisomer and label it appropriately.
Chem 33, Kanan & Stack, 2012, PS 4; pg 5
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11. Indicate whether each of the following pairs of compounds are identical/meso, enantiomeric, or diastereomeric.
Cl
3
C
CH
3
Cl
Cl
Cl
3
C
CH
3
Cl
Cl
CO
2
H
I
CO
2
H
I
C
H
3
C
H
3
C
CH
3
H
C
H
3
C
H
3
C
H
CH
3
OH
Et
OH
Et
OH
OH
OH
H
H
Et
H
H
Et
H
H
H
H
HO
O
O
CH
3
OH
H
3
C
CH
3
HO
CH
3
Br
Br
Br
Br
CH
3
H
3
C
H
3
C
CH
3
H
3
C
CH
3
CH
3
H
3
C
Chem 33, Kanan & Stack, 2012, PS 4; pg 6
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- Spring '10
- Dunremember
- Chem, H3C, Conformational isomerism, kcal mol-1, Isomer
