CM1121 Tutorial 1 (Chapters 2 & 4)

1.

Draw and name a structure corresponding to each of these descriptions.

(a)

An aromatic compound containing one benzene ring with the following

substituents: two chlorine atoms having a para relationship, a nitro group having
an ortho relationship to one of the chlorine atoms, and an acetyl group having a
meta relationship to the nitro group.

(b)

An alkyne having a trifluoromethyl substituent at one end and a chain of three

carbon atoms at the other with a hydroxyl group on the first atom, an amino
group on the second, and the third being a carboxyl group.

(c)

C3H3N which contains a carbon-carbon double bond and a carbon-nitrogen

triple bond

2.

What kind of hybridization do you expect for each carbon atom in the following
molecules?

H
C
C
H

C
H

3.

H2
C

H2
C

H
C
H2

N
+

CH3

CH2OH

HO

O
H

C CH3
H2

C
H
HO

H
Procaine

C
C

C
OH

Ascorbic acid

Allene, H2C=C=CH2, is somewhat unusual in that it has two adjacent double bonds.
Draw a picture showing the orbitals involved in the and bonds of allene. Is the
central carbon atom sp2- or sp- hybridized? What about the hybridization of the
terminal carbons? What shape do you predict for allene?
Allene is related structurally to carbon dioxide, CO 2. Draw a pciture showing the
orbitals involved in the and bonds of CO2 and identify the likely hybridization fo
carbon.