Problem Set 1
Chapters 1 and 2, Structure, Bonding, Reactivity
Due: Monday, September 14, 2009
John Dalton (1766-1844) |
John Dalton's formulation of an Atomic
Theory in the first decade of the
19th century provided a theoretical basis for understanding
chemical behavior. In addition to defining the Law of
Multiple Proportions, he also formulated the Rule of
Greatest Simplicity, which held that water was a binary
compound, OH. (Note: Dalton did not use our modern symbols,
which came to us from Berzelius,
but rather circles that were distinguishable
from one another.) Dalton established the combining masses
of H to O in water as ~1:6. This ratio was later refined to
1:8. The Rule
of Greatest Simplicity, which was
at odds with Gay-Lussac's Law of Combining Volumes of Gases, did not lead to a correct
formulation for the atomic composition of water. Moreover,
although there was agreement regarding the combining masses
of atoms in the first half of the nineteenth century, there
was disagreement as to the unit mass
of the common atoms encountered in organic chemistry:
hydrogen (1), carbon
(2x6 or 1x12), oxygen (2x8 or
1x16). Since hydrogen was the lightest of the elements, it
was assigned a mass of one, a notion that is unrelated to
today's mass of hydrogen owing to the presence of a single
proton in the hydrogen nucleus. Berzelius's proposal of a
mass scale based upon O = 100 would have worked as well. For a Brief History of Organic Chemistry (PowerPoint), click here.
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1. a) Identify the four
functional groups in azithromycin marked by arrows. |
3. For each of the following acids or bases, identify the corresponding conjugate base or acid, whichever is appropriate. The pKa table may be of help.
a) LiNH2b) acetic acid
c) KOCH3
d) CH3CH2MgBr
e) C2H5OH
4. Arrange the acids and conjugate acids in
problem #3 in order of increasing acidity (decreasing
pKa).
5. Draw an orbital picture for the monomer,
vinylacetylene (CH2CHCCH). Identify π-bonds and
hybridization.
6. A normal alkane, CnH2n+2, is found to have a
vapor density of 1.78 mg/mL at 300oC and 740 mm pressure.
Using the ideal gas law, determine the structure of the alkane. (In
the early 19th century, the vapor
density of an unknown liquid was compared
to the vapor density of air to determine the liquids molecular
weight.)