Organic Chemistry I

Professor Carl C. Wamser

Chapter 1 Quiz

1. (4 points) Rewrite the two compounds below to show all the bonds and all the lone pairs.
Describe the hybridization and molecular geometry about each carbon.
(Accurate pictures will be helpful but not required if your description and hybridization are correct).

a) (CH3)2CHOH

all carbons are sp3 and tetrahedral

b) CH2=CHNH-

all carbons are sp2 and trigonal planar

2. (2 points) Write two good resonance forms for CH2N2 . The atoms are bonded CNN, with no rings.

3. (4 points) Complete acid-base reactions for each of the following.
Predict whether each equilibrium will lie farther to the right or to the left.

a) CH3OH + OH- <===> CH3O- + H2O

favored to the right (pKa 15.2 vs 15.7)

b) CH4 + NH2- <===> CH3- + NH3

favored to the left (pKa 60 vs 36)