Chemistry 2500 A
Fall 2001
Covers Chapter 6 of Sorrell, “Organic Chemistry”
Fifth assignment
Self-Study Assignment
Do all the exercises in Chapter 6 (6.1 to 6.40).
Note: there is from time to time new material introduced in the Exercises; you are responsible for such material. In addition, the
“Solutions to Exercises” give step by step guidance for solving certain types of questions. You may find the author’s
suggestions helpful in your own work.
1. (a) Classify each of the following reactions as a substitution, addition, elimination, oxidation, reduction or rearrangement.
(b) Calculate the number of millimoles of each reactant and product, and calculate the percent yield.
NH
(i)
CCl3
C
N
+
CCl3
H2N
35 g
N
H
10. g
11.2 g
O
(ii)
CCl3
3.
Cl
SOCl2
C
CCl3
N
H
7.55 g
2.
C
C
N
7.78 g
Write an acid-base reaction for the following compound with (a) aqueous sodium hydroxide, and (b) ethanolic ammonia.
For each reaction, predict in which direction the equilibrium lies. Justify your answer.
SH
Br
The following pericyclic reaction is energetically favourable. Illustrate movement of electrons to account for formation of
the product, and sketch a reaction profile diagram as discussed in lecture (e.g. Fig. 6.2) for this reaction.
••
••O
+
•
+
O ••
- •••O• •
••
•O
•
• O••
•
•
•
O•
•
4.
(a) The amino acid arginine (p.1265) normally functions as a base in biological systems. Draw the structure for the side
chain of arginine in its conjugate acid form. What is the approximate pKa value for the conjugate acid form of the arginine
side chain? (Hint: a nitrogen atom which is part of a double bond, including aromatic N atoms such as in pyridine, are
more basic than nitrogen atoms which have only single bonds to them.)
(b) Write the neutral arginine molecule in its zwiterionic form.
5.
Classify the following biological process according to the fundamental reaction types of substitution, addition or
elimination. What molecules, atoms, or groups are lost, added or replaced?
The first step in the biosynthesis of alanine:
H H
H H
CH3
O
CH3
+
+
N
H
N
H
O
H
O
COO
H
COO
+
+
O
O
P
P
O
O
O
O
+
N
H
CH3
+
N
H
CH3