Isomerism Practice

1. Explain briefly with examples: a. Diastereomerism b. Fischer projection c. Delocalisation of electrons d. Resonance energy e. Primary, secondary, tertiary and quarternary carbon atoms 2. Give examples to differentiate between the following: a. Resonance and Tautomerism b. Racemic mixture and meso compound c. Assymmetric and Dissymmetric molecules d. Functional group isomers and Tautomers e. Conformations and Configurational isomers 3. Draw all the possible isomers which bear the name dimethyl naphthalene (one of

them is

4. Draw all possible structural isomers for C6H13Cl and provide their IUPAC names.

Indicate which ones will have enantiomers. 5. In each of the following sets indicate (with explanation) whether they are same compounds or are isomers. In case they are isomers, indicate the type of isomerism
COOH H HOOC OH
CH3
CH3

COOH HO HOOC
and

OH H

H H OH

a.

b.

CH3

and

CH3

O
c. d.

OH H
and and

H3C

H2C

e.

and

6. Draw the Newman projection formula of conformers of 1-chloro propane to illustrate the terms staggered, eclipsed, gauche and anti. Indicate their relative energies. 7. Presence of assymmetric carbon atoms in an organic compound is a necessary and sufficient condition for optical activity - is this statement true or false? Explain with examples. 8. Write down the structures of the following and indicate if any one of them is optically active: (a) n-butyl bromide (b) sec-butyl chloride (c) isobutyl chloride (d) 2-buten-1-ol (e) neopentyl alcohol