

Problem 14
After examining the potential maps for LiH, HF, and H2, answer the following questions:
<IMAGE>
a. Which compounds are polar?
b. Why does LiH have the largest hydrogen?
c. Which compound has the hydrogen that would be most apt to attract a negatively charged molecule?
Problem 17f
Draw the Lewis structure for each of the following:
f. NaOH
Problem 18a
Draw two Lewis structures for C2H6O.
Problem 18b
Draw three Lewis structures for C3H8O.
Problem 19a,b,c
Draw the lone-pair electrons that are not shown in the following condensed structures:
a. CH3CH2NH2
b. CH3NHCH3
c. CH3CH2OH
Problem 20a,b
Draw condensed structures for the compounds represented by the following models (black = C, gray = H, red = O, blue = N, and green = Cl):
a. <IMAGE>
b. <IMAGE>
Problem 20c,d
Draw condensed structures for the compounds represented by the following models (black = C, gray = H, red = O, blue = N, and green = Cl):
c. <IMAGE>
d. <IMAGE>
Problem 22a,b
Change the following condensed structures to Kekulé structures:
a. CH3NH(CH2)2CH3
b. (CH3)2CHCl
Problem 28
Explain why a σ bond formed by overlap of an s orbital with an sp3 orbital of carbon is stronger than a σ bond formed by overlap of an s orbital with a p orbital of carbon.
Problem 30
Put a number in each of the blanks:
a. ___ s orbital and ___ p orbitals form ____ sp3 orbitals.
b. ___ s orbital and ___ p orbitals form ____ sp2 orbitals.
c. ___ s orbital and ___ p orbitals form ____ sp orbitals.
Problem 32(3)
For each of the given species:
a. Draw its Lewis structure.
b. Describe the orbitals used by each carbon atom in bonding and indicate the approximate bond angles.
3. CCl4
Problem 32(2)
For each of the given species:
a. Draw its Lewis structure.
b. Describe the orbitals used by each carbon atom in bonding and indicate the approximate bond angles.
2. HCN
Problem 32(1)
For each of the given species:
a. Draw its Lewis structure.
b. Describe the orbitals used by each carbon atom in bonding and indicate the approximate bond angles.
1. H2CO2
Problem 32(4)
For each of the given species:
a. Draw its Lewis structure.
b. Describe the orbitals used by each carbon atom in bonding and indicate the approximate bond angles.
4. H2CO3
Problem 33
Predict the approximate bond angles in
a. the methyl cation.
b. the methyl radical.
c. the methyl anion.
Problem 34
According to the potential map for the ammonium ion <IMAGE>, which atom has the greatest electron density?
Problem 39a
Describe the orbitals used in bonding and the bond angles in the following compounds:
a. CH3O-
Problem 39c
Describe the orbitals used in bonding and the bond angles in the following compounds:
c. H2CO
Problem 39d
Describe the orbitals used in bonding and the bond angles in the following compounds:
d. N2
Problem 39e
Describe the orbitals used in bonding and the bond angles in the following compounds:
e. BF3
Problem 44b
What is the hybridization of each of the C, N, and O atoms in the following compounds:
Problem 45c,d
Predict the approximate bond angles for
c. the H—C—N bond angle in (CH3)2NH.
d. the H—C—O bond angle in CH3OCH3
Problem 46a,b,c
Which of the following molecules would you expect to have a dipole moment of zero?
a. CH3CH3
b. H2C═O
c. CH2Cl2
Problem 46d,e,f
Which of the following molecules would you expect to have a dipole moment of zero?
d. NH3
e. H2C═CH2
f. H2C═CHBr
Problem 46g,h
Which of the following molecules would you expect to have a dipole moment of zero?
g. BeCl2
h. BF3
Problem 47
Account for the difference in the shape and color of the potential maps for ammonia and the ammonium ion in Section 1.11.
<IMAGE>
Problem 48
If the dipole moment of CH3F is 1.847 D and the dipole moment of CD3F is 1.858 D, which is more electronegative: hydrogen or deuterium?
Problem 50a
Which of the following has a polar covalent bond?
CH3NH2 CH3CH3 CH3F CH3OH
Problem 50b
Which of the following has a bond closest to the ionic end of the bond spectrum?
CH3NH2 CH3CH3 CH3F CH3OH
Problem 51c,d
What is the hybridization of all the atoms (other than hydrogen) in each of the following?
What are the bond angles around each atom?
c. -CH3
d. ⋅CH3