Review – Ch 1 and 2
1. Write the electronic configuration for phosphorus.
2. a. Write the Lewis Dot structure for CH3CH2CN
b. Write the Lewis Dot structure for CH3OC(O)CH3
c. The following was a Lewis Dot structure drawn for CH2CHCH3. What two problems do
you see with the answer?
H
H
H C C C H
H
H
3. a. Write the molecular formula for a compound whose empirical formula is CH2O but
really has SIX carbons in its structure.
b. Write the empirical formula for C12H24O4
4. Structure Questions
a. Convert the following line bond structure to a condensed formula:
H
H
H
H
H
H C H
H
C
C
C
C
C
H
H
H
O
H
H
H
b. Convert the following line bond structure to a skeletal structure:
H
H
H
H
C
C
C
H
H
C
H
O
H
C
C
H
H
c. What’s technically incorrect about the following two structures (according to class
lecture)?
H
As a line bond structure:
H
H
H
C
C
N
H
H
H
H
H
As a Lewis Dot structure: C
H
O
H
d. Convert the following skeletal structure to a condensed formula:
O
e. Convert the following condensed formula to a skeletal structure:
CH3CH(Br)CH2CH(CH3)2
5. Hybridization questions:
a. What is the hybridization of N in:
H
H
H
H
C
C
C
H
H
N
H
H
C
C
H
H
H
b. What orbitals make up the O-C bond in:
H
H
H
H
H
H C H
C
C
C
C
H
H
H
H
O
H
c. What is the geometry of the C1 in:
H
H
H
H
H
H
C
C
C1 C
C
C
H
H
H
H
H
H
d. What is the bond angle for H-N-C in:
H
H
H
H C
H
C
C
C
H
H
H
N
H
e. List the three reasons using hybrid orbitals is better than forming bonds with p
orbitals.
6. Calculate the formal charges
a. on oxygen in:
H
H
H
H
C
C
C
H
H
O
H
b. on the C1 carbon in:
2 H
H
O
H
C1
C
C
H
H
7. Acid-Base Questions
a. Identify the acids and bases in the following reaction:
NaHCO3 + H2O ßà H2CO3 + NaOH
b. Identify the acids and bases in the following reaction:
-
CH3COOH + H2O ßà CH3COO + H3O
+
c. Which of the following is the stronger acid?
i. HOCH2CH3 (pKa = 16) vs. CH3NO2 (pKa = 10.2)
+
ii. NH4 (Ka = 5.5x10-10) vs. C6H5CO2H (Ka = 6.31x10-5)
d. Which acidic proton (underlined, with pKa values shown) has the stronger, more
reactive conjugate base?
O
O
vs
O
H pKa = 26.3
H pKa = 23.6
e. Which acidic proton (underlined, with pKa values shown) has the weaker, more stable,
conjugate base?
O
O
O
F3C
H pKa = -0.25
O
vs
H pKa = 3.44
O2N
f. Calculate the pKa if the Ka is 8.96x10-4
g. Calculate the Ka if the pKa is 13.6.
h. In which direction will the equilibrium shift in the following reaction?
CH3CH2CH2CO2H + NaOCH3 ßà CH3OH + CH3CH2CH2CO2Na
pKa = 4.86
pKa = 16
3 i. Circle the Lewis Bases. Put a box around the Lewis Acids.
H
N
H
C
H
C
H
O
H
4