School of Physical & Mathematical Sciences

Division of Chemistry & Biological Chemistry

H3 Organic Synthesis and Mechanism - Tutorial 3

Stereochemistry

1) Sighting along C2-C1 axis, draw the Newman projections of the most
stable conformation for the following compounds:
Et
1
1 1
Br 2 2
2
Cl
HO H Cl
Do the same as the above but sight along C1-C2 axis.

2) Draw the skeletal structures for the following Newman projections:

Cl OH OH
H H H H H Et

H H Me H Me H
Cl Me OH

3) For each of the compounds below, draw the 2 chair conformations:

2
1 2
1 H H
Et H
4 4
H Me
5
HO H H
5

For the 2 skeletal structures above, draw the 2 Newman projections of the
2 chair conformations by sighting along both C1-C2 and C5-C4.
School of Physical & Mathematical Sciences
Division of Chemistry & Biological Chemistry

4) How many stereoisomers are possible for the following compounds?

O HO

OH OH
Cl

5) Determine the E/Z configuration for the following alkenes:

Br
Cl
H Cl

6) Determine the R/S configuration for all the chiral centres present in the
following compounds:
HO OH
OH Br
Cl Br CH3 H 3C H
CH3O CH3
H3C H Ph H CH3
Br
O
Br
Which compound is achiral?

7) List out all the isomers of C4H7Cl. Identify the pairs of enantiomers and
diastereomers.