Problem Set 1
Chapters 1 and 2
Due: Monday, September 13, 2004
1. For each of the following substances,
identify the functional groups present in each one.
[Functional groups are listed on the inside front cover
of your text.] Draw line-angle formulas for b-e and
g. 2. Ever since Lavoisier
established the importance of gravimetric analysis and the
principle of the conservation of mass in chemical reactions,
chemists have been able to determine the mass of carbon and
hydrogen in organic compounds. While combustion gives carbon
as CO2 and hydrogen as H2O, oxygen is
determined by difference. The problem was that there was no
universal acceptance through the late 1800's as to the mass
of carbon (6 or 12?) and oxygen (8 or 16?). In 1852,
Alexander
Williamson reported on the
formation of a mixed ether, ethyl methyl ether. Fortunately,
Williamson subscribed to the scheme H=1, C=12, and O=16.
[Reading Assignment: A
Brief History of Organic
Chemistry.] Using his data on
pages 232-233 in the
accompanying paper, confirm the
empirical formula obtained by Williamson given the mass of
the sample and the mass of combustion products. Using the
vapor density of the ether compared with the density of air,
whose effective "molecular weight' is known, confirm the
molecular formula of the ether. You need not use the data
relating to the "globe". 3. For the hydrocarbon shown below,
identify the hybridization of each of the carbon atoms.
Redraw the structure showing p-bonds
with p-orbitals. Chime version. Get Chime here. 4. For each of the following acid-base
reactions, provide the products of the reaction (conjugate
acid and conjugate). Provide equilibrium arrows to show the
direction of the equilibrium. Use the data in
the
pKa
table to determine the direction
and magnitude of the equilibria. 5. For each of the species listed below,
draw Lewis structures. Draw bonds as lines and non-bonded
electrons as a pair of dots. Provide charges and resonance
structures where applicable. 6. Which of the following compounds have
a net dipole moment? Explain and illustrate.