zj
1/ If "
Name:_ _ _ _~(""\_'-'_l.l__~_
MOct,2015
5C225 Quiz, ChapterY,
Prof. Urban
1. Identify these pairs of compounds as identical, structural isomers, enantiomers, or
diastereomers. (2 points)
Br
~
~
I 1) e;,rIf Cift.
Br
0
0
~
~
H
OH
HO
H
OH
H
H
]; (M Te I2-f!O yt tlLS
OH
OH
OH
2. For each structure below:
a. Label as Chiral or Achiral
b. Circle any chirality centers present
c. Assign R/5 configuration to any chirality centers present.
CI
HO
,
/
lt~uP
~H t>t@ Ct­
H C,® X'
s
~. ~C~
H
b==c=c(
~
(4.5 points)
3
OH d.;.. tJ.. C("ut;
~j'r()\lt;~
H
CH 3
~
(\0
C~)
(j)
pOin~:s
f-a1.s..f
().rA lyJ
1. True or False? If false, indicate why the statement is false.a,....
(1.5
a. Enantiomers must exhibit identical properties in a-eftirel environment.
~~ ,. iJ~{.;cA'·
.to ~;f-tU~ ':
b. Molecules that possess chirality centers must be chira!.
Mes~ ~fo{jt\Js
P"SSlSf
@
~~ ~
VfJN. wrf
c. A reaction taking place on an achiral molecule that generates a new chirality center
must produce a racemic mixture if run under achiral condition@
o1ft
H~ _ _"'>
~ /kh.'rol
C~-(J~~t
~~
~
glt
+ ~
:
~
~D~/6
~rv~
~
2. Provide the following structures:
(2 points)
/.l a. The Newman projection of (R)-2-butanol when viewed looking down the C2-C3 bond in
the conformation where C1 and C4 are anti to each other.
\..y
eJl"~_il4 _
\+
~o\-\
\~l-\
0)/¥
, ) {l-
C\{-3
b.
The Fisher projection of meso-2,3-dichlorobutane.
c.
The enantiomer of the molecule below.
yC
CI
d. A diastereomer of the molecule below.
OH
yY
CI
OH
fIf
()~+
~
Ct
0\-\
rJY" O~
~
l
CJ..
~\~
ex. ~- pk.