CHEM 313 Quiz #2 Fall 2001
Name: ____________________________ Student #: XXX-XX- __ __ __ __
1. (4) Draw an example of each of the following functional groups.
alkene alcohol aldehyde carboxylic acid
2. (2) (a) What orbitals overlap to form the bond between the two carbons atoms in the
following molecule? Is the bond a sigma or pi bond?
H3C C N
3. (5) Beside each arrow, indicate (a) the hybridization of the atom (b) the approximate bond
angle around the atom (c) for the starred (*) atoms, answer (a) and (b) AND indicate the
partial charge on the atom.
4. (9) For EACH of the following pair of molecules, what BEST describes the relationship
between them. (possible answers: different, same, constitutional isomers, conformational
isomers, resonance structures, enantiomers, diastereomers). You can use an answer more
than once. Please place the answer in the left or right margin.
(a) O O (f)
H H vs. Br Br
CH3 H Br OH
H vs. H H HO CH3
H (g) H3 C H
H3C Br H3C CH3 H H vs.
H3C Br Br CH3
CH3 H CH3
H H vs. H O OH
Br H3C H
H H H3 C H
Cl (i) vs. H
(e) vs. CH3
H Br CH3
Cl Cl CH3
5. (4) Draw a Fischer projection for each of the stereoisomers of the following molecule.
H3C C C CH3
6. (4) Are the two substituents on EACH cycloalkane cis or trans?
Br H Br Br
H H H H
7. (4) What is the absolute stereochemistry (R or S) of each of the chiral carbons?
F OH H CH2CH3
8. (5) Draw (a) gauche 1-bromopentane as a Newman projection looking down the C2-C3 bond
9. (5) Draw five constitutional isomers of C3H6O (there are 9 total).
10. (2) Extra credit (placed here to save space). Draw all possible hydrogen bonding interactions.
11. (8) Name the following molecules.