Chapter 3 - Solutions

1. a.

N
N
H H
H H

From the Lewis structures shown above, NH 2 has two lone pairs; therefore, the
VSEPR electron arrangement is AX2E2 and the angle is 109. NH2+ has one lone
pair; hence the VSEPR electron arrangement is AX2E and the angle is 120.

b. The N 2pz orbital does NOT participate in the hybridization for NH2+, because the
VSEPR electron arrangement is AX2E and the angle is 120. Hence the
hybridization for N is sp2, which means that one 2p atomic orbital is not used in the
hybrid orbitals. Because NH2+ lies in the xy plane, according to the picture above,
2px and 2py atomic orbitals participated in the hybridization and not 2pz.

c. The N 2pz orbital does participate in the hybridization for NH2 because the
VSEPR electron arrangement is AX2E2 and the angle is 109. Hence the
hybridization for N is sp3, which means that all the 2p atomic orbitals participate in
forming the hybrid orbitals.

3.
H
H H H
C C N C
H H HC CH HC CH
C C
HC CH HC N HC N

HC N H H
H
H
O O C
HC HC N
CH CH CH
HC HC HC
C C N
H H
CH2 C CH2 CH2 C O

5. a.
+ - +
O
+

-
+ +
+ C
H +
- + + H
N
+
+

b.The high rotational barrier (and the 120 bond angles about N) suggest a significant
contribution from the resonance form shown below having a C=N double bond.

C
H
H N

H
c.
O + -

C + -
+ -
N
7. a.
sp3
Ca ___________
H O
sp2
Cb ___________ O

sp2
Oa ___________ H C C O O N O

sp3
Ob ___________ H

sp3
Oc ___________
sp2 H O
Od ___________ O

sp2
Oe ___________ H C C O O N O

sp2
N ___________ H

b.
px
Cb ___________
px
Oa ___________
px
Od ___________
px
Oe ___________
px
N ___________
9.

H H H H
C C C C
H C C H H C C H
C C
H H

H H H H
H
H
C C C C C C

C C C C C C
H H H H H
C C C H

H H H

All of the carbons are the same hybridization, which is sp2, because of the multiple
resonance structures of the molecule. Orbitals that are sp2 hybrid have an angle of
120C, and therefore the molecule is planar.