Organic Chemistry – CHM 220-2
Problem Set #1
Due Feb 6, 2006
25 pts total
1. Consider the following condensed molecular structures (6 pts = 2 pts each):
a. (CH3)2CHC(CH3)2CH(I)CH(OH)COOCH3
b. CH3C6H4CH2CHCHCH2C(Br)(CH3)2
c. (CH3)3CCCCH2CH2COCl
For each structure, convert the condensed structure into a kekule structure, a bond-line structure,
a 3-D structure using dashes and wedges, and use a computer program to draw the molecule. I
would encourage you to practice drawing first, before you use the computer program.
2. Redraw each of the following molecules and draw bond dipole moments for each. Include any
appropriate charges or partial charges, as necessary. Are there resonance structures that change
the location of any electron density? Explain briefly what the dipole means in regards to the
reactivity of the molecule. What is the shape of the molecule (think about it as a combination of
the shapes of each major atom – There is no one single answer)? Explain briefly. (8 pts = 2 pts
each).
2a. 2c.
2b. CH3CHCHCHO
CH2CHNH2C6H5COCH22d. CH2CHCHNH2
3. Consider the following molecule, a derivative of lysergic acid diethyl amide (LSD). (5 pts):
N
N
H
O
NH
O
OH
O
OOH
a. Redraw the structure on your paper (take your time and practice, you will not be graded
for your artistic abilities, but practice makes perfect) What is the molecular formula and
molecular mass of this molecule? (1pt)
b. Label the hybridization for at least 8 non-hydrogen atoms. Ensure that you label identify
at least one atom from each type of hybridization. (2 pts)
c. Circle and label all functional groups. (2 pts)
4. Consider the following Acid – Base reactions: (6 pts = 2 pts each)
a. HCl + H2O
b. CH4 + NH2-
c. CH3COOH + CH3COCH3
Draw the Acid – Base reaction mechanism using the arrow pushing formalism. Using the
appropriate values, calculate the equilibrium constant for the reaction. What does each
equilibrium tell us about the likelihood of reach reaction?