School of Physical & Mathematical Sciences = NANYANG
Division of Chemistry & Biological Chemistry
UNIVERSITY
H3 Organic Synthesis and Mechanism
Stereochemistry
utorial 3
1) Sighting along C2-C1 axis, draw the Newman projections of the most
stable conformation for the following compounds:
1
HO.
cl
Do the same as the above but sight along C1-C2 axis.
Ase (oe ot & eM. co.
H y H x, He
yl h 7 # Fe &
& 4 0 H
4 n7 cy ou ch Hy Sh
ct, on, ch,
a oH OH
Mac bc Het
HTH Me PH Me“ TH
a Me on
cA ng on
ae ey oY
rat o
~ toe.
we
3) For each of the compounds below, draw the 2 chair conformations:
faa
aCe
re
For the 2 skeletal structures above, draw the 2 Newman projections of the
2,ghair conformations by sighting along both C1-C2 and C5-C4.
x et 1
f BAL >
hy ‘ warn
”School of Physical & Mathematical Sciences = ang
Division of Chemistry & Biological Chemistry Gy UNIVERSITY
4) How many sigreciomers ‘are possible for the following compounds?
HO te
{ eo ab : peittions
ANN Re]
OH fa | ‘OH
ts
a? .
2*6
ulcer}
ole
5) Determine the E/Z configuration for the following alkenes:
ei
enue 0)
L a yo bl%
cl)
6) Determine the R/S configuration for all the chiral centres present in the
following compounds:
cl ye CHs HgC.
Yoon” pion Re,
Welt
Be
Hsc“R
oie
Which compound is achiral?
wy,
7) List out all the isomers of C.H-Cl. Identify the pairs of enantiomers and
diastereomers.
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