Chemistry Reference
In-Depth Information
a.
5.35
C
H
C
H
3
3
H
and
H
CH 3 CH 2
HS
C 6
H
I
5
b.
CH
CH 3
CH
Br
2
CH 2
CH 3
and
CH 3
CH 3
CH 2 CH 2
HOCH 2
CH
O
OH
There are many ways to write these structures. They have been drawn here by
putting the lowest-priority group receding away from the viewer and the remaining
three groups in a clockwise (a) or counterclockwise (b) array, with the highest-priority
group at the lower right extending toward the viewer.
5.36
In each case, write down the groups in the proper priority order. Then view the
stereogenic center from the face opposite the lowest-priority group and determine
whether the remaining array is clockwise ( R ) or counterclockwise ( S ). If you have
difficulty, construct and examine molecular models.
a.
Carbon-5
CH 3
H
O
5
C 2 C
>
C 2
C 2
>
C 3
>
H
therefore R
Carbon-2
2
O
O
H
CH
(
CH 3
) 2
C
>
>
C 2
>
H
CH CH 3
(
) 2
therefore
S
b.
C O 2 H
H 2 N
H
N 2
>
CO 2 H
>
CH 2 OH
>
H
therefore
S
CH 2 OH
c.
C
H 3
H
N
CH 2
H 2
NH 2
>
CH 2 CH
>
CH 3
>
H
6
5
therefore
S
5.37
O
C
H 3
H
*
C
H 2
C
H 3
(+)-carvone
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