CHEM1280 Problem Set 1

(Due on 26 Sept. 2012)

1. For each of the following species, give the hybridization of the central atom:
a. NH3 sp3 b. +NH4 sp3 c. –CH3 sp3 d. C(CH3)4 sp3 e. •CH3 sp2 f. +CH3 sp2
g. HCN sp h. H3O+ sp3
(note: There was a typo on the question 1e, –CH3 should be •CH3. This question was
neglected during grading.)

2. Draw the condensed structure of a compound that contains only carbon and hydrogen
atoms and that has
a. three sp3carbon. CH3CH2CH3
b. one sp3 carbon and two sp2 carbons. CH3CH=CH2
c. two sp3 carbons and two sp carbons. CH3C≡CCH3 or CH3CH2C≡CH

3. Predict the approximate bond angles:

a. the H—C—O bond angle in CH3OH b. the C—O—H bond angle in CH3OH
3
sp , about 109° sp3, about 109°
c. the H—C—H bond angle in H2C=O d. the C—C—N bond angle in CH3C≡N
2
sp , about 120° sp, 1800
4. In the following molecules, assign the missing formal charges to the atoms that have
formal charges not equal to zero.

5. (1) Which of the indicated bonds in each compound is shorter?

(2) Indicate the hybridization of the C, O, and N atoms in each of the compounds.

6. Sodium methoxide (CH3ONa) has both ionic and covalent bonds. Which bond is ionic?
How many covalent bonds does it have?

O-Na is ionic, [CH3O]-[Na]+. It has four covalent bonds.

7. Draw resonance contributors for the following species. Indicate which are major
contributors and which are minor contributors to the resonance hybrid.
8. Are the following pairs of structures resonance contributors or different compounds?

The structures in each of the above pairs are different compounds.

9. Rank the following bases in the order of decreasing basicity. Briefly explain your
reasoning.
CH3S−, CH3O− and CH3NH−

CH3S− is more stable than CH3O− because S is much larger than O; CH3O− is more stable
than CH3NH− because O is more electronegative than N.
Therefore basicity: CH3S− < CH3O− < CH3NH−.
10. Rank CH3OH, H2O, H3O+ and CH3OH2+ in the decreasing order of acidity according to
the following equilibriums:

Acidity: H3O+ > CH3OH2+ > H2O > CH3OH.