School of Physical & Mathematica l Sciences

Division of Chemistry & Biological Chemistry

H3 Organic Synthesis and Mechanism - Tutorial 1

Structure, Bonding, Resonance and Acid-Base Theories

1) For the following compounds, determine the formal charges for the atoms
marked with an asterisk (*):
O* H
H H H O*
O* H2C* N* N*
C*
H H H O*

2) Identify the most acidic H in the following compounds:

O
O H
N
OH OH
H

O O O O O
OH
O

3) Use the pKa table supplied to answer the following questions.

a) List the following in order of increasing acidity:

A B C D E

O N N
H H HO CH3 H CH3
O

b) List the following in order of increasing basicity:

O O
S OH
OH
O
F G H I J

c) By comparing pKa values, predict the predominant species at

equilibrium when you mix....
i) compound H with compound D
ii) compound A with compound F
iii) compound G with compound C
School of Physical & Mathematica l Sciences
Division of Chemistry & Biological Chemistry

4) Which of the following pairs represent resonance structures?

O O
and
OH O and

O O
O OH
and
and

O O

O O
and
H 2C N and H2C N
O O

H H
H3C N N and H3C N N O O
and

H H H H

5) For the pairs of resonance structures above, indicate which is the more
stable resonance contributor.
School of Physical & Mathematica l Sciences
Division of Chemistry & Biological Chemistry