Problem Set 1
Chapters 1 and 2
Due: Monday, September 12, 2005
Antoine
Lavoisier
(1743-1794) French scientist who developed dual names
for chemical compounds and formulated the the law of the
conservation of mass. His work in chemical analysis led to
the overthrow of the phlogiston
theory (Stahl) by correctly
explaining the role of oxygen in combustion. Jons
Jacob Berzelius
(1779-1848) Swedish chemist who gave us the modern
symbols of the elements and discovered many of them. He was
a proponent of the dualistic (electrochemical) theory and he
recognized and defined the property of isomerism.
1. In 1818,
William
Prout, MD, presented a
paper
before the Royal Society of London on the oxidation of uric
acid (1), the cause of gout. Treatment of uric acid
with nitric acid formed purpuric acid 2. Treatment of
purpuric acid with ammonia gave a purple ammoniumsalt
3, which was used as a dye (Murexide).
Prout conducted a combustion analysis on 3 and found
the percentages of carbon, hydrogen, nitrogen and oxygen
found on page
423. a) Why do these four percentages add up
so closely to 100% (99.98%)? b) What atomic masses did Prout use to
determine the number of each type of atom? c) In determining the ratio 2:2:2:1, is
there anything suspicious about the numbers? d) Knowing what you know from general
chemistry, what would you suggest as the simplest empirical
formula for 3, based upon the data
presented? e) Of course, Prout had no idea about the
structure of 3. However, compare his empirical
formula with the molecular formula derived from 3.
How well did he do? f) What is the structure of purpuric
acid? g) Purpuric acid has a pKa=0.
What does this value mean? h) Using resonance structures, show why
you would expect purpuric acid to be more acidic than
acetic
acid. 2. Define the functional groups or class
of compound indicated by the circles in the following
structures. [The inside of the front cover of your text
is helpful. Print the structures and write the answers next
to the circles.] 3. For the compound
(C4H5N) shown below, identify the
hybridization of each of the carbon and nitrogen atoms.
Redraw the structure showing π-bonds with
p-orbitals. Chime version. Get Chime here. (First get Netscape 4.8 here.) 4. Draw the structures that have the
molecular formula C4H10S. Some of the
structures are soluble in aqueous NaOH; others aren't. Use
the pKa
table to determine which of the
two groups is soluble in base. Explain and
illustrate. 5. Assign charges and non-bonded
electrons to each of the following nine species or
compounds. If resonance structures apply, draw
them. 6. Which of the following compounds have
a net dipole moment? Which ones are planar compounds?
Compounds b) and c) are at best identical, or at worst,
mirror images. Explain and illustrate.