Stereoisomer isomenthol and the 1s2s5r stereoisomer

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

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