CML 100 Organic Chemistry (Tutorial 1)

Answer these following questions:

1) Classify each pair of compounds as constitutional isomers or stereoisomers and justify.

a) b)
2) Locate the stereogenic centres in each molecule.

a) b) c)
3) Draw the R- enantiomer of these molecules.

a) b) c)
4) Locate the stereogenic centre in each compound and draw both enantiomers.

a) b)
5) Draw the mirror image of each compound.

a) b) c)
6) Assign each compound as R or S.

a) b) c) d) e)
7) Draw structures for each of the following molecules and assign the stereogenic centre:
a) (S)-1-Bromo-1-chlorobutane b) (2R,3R)-2,3-Dichloropentane
8) Indicate whether each of the following pairs of compounds are identical or enantiomers, diastereomers, or
constitutional isomers:

a) b) c)
9) Draw the Zigzag projection of these following compounds:

a) b)
10) Draw the Newman projection of these following compounds:
a) cis-1,3-Dihydroxycyclohexane
11) Draw the Fischer projection of these following compounds:
a) (S)-1-Chloro-2-methylbutane
c)
b) trans- 1-Chloro-4-ethylcyclohexane
b) (2R,3S)-2,3-Dibromohexane