Assignment 5 Bonding

(Submission due September 26)

Lewis Structure, Resonance, Conjugation, Hybridization, Molecular

Orbitals, Bond Energy, Bond length, Bond angle, Dipole moment.
1. Assign proper bond lengthsto the following bonds (a h) by selecting
values from the Pool

Pool : 1.06,1.08, 1.10, 1.21, 1.34, 1.46, 1.50, 1.53 (all values in Angstrongs)
2. Within each of the following groups of compounds arrange according to
increasing lengths of the indicated bonds.
a.

CH3

b.

CH3C

OH CH2
,
N CH3
,

O HC(OCH3)
O
,
NH2 CH2
NCH3
,

3. Explain the bond angles in

O
N 1300

O
H

102

4. Classify the following molecules as polar or non polar ( use VSEPR theory
to determine shapes )
AX3E2
AX4E2
AX4E
AX3
AX2E3
a.
b.
c.
d.
e.
5. Arrange the molecules in the order of increasing dipole moments :

H
C

Cl

H
C

C
H

a. H
, H
CO2
H2CO
b.
, CO ,
OH2
OF2 Cl2O
c.
,
,

Cl

H
C

C
Cl

, Cl

C
H

6. Given below are some resonance structures of a number of species.

Determine the formal charge on each atom and then, if possible identify
the more important of the structure pairs.
a.

and

b.

and

c.

and

7. state the hybridization of the highlighted atoms in the following

molecules
SF4
(CH3)2Be
SF6
BCl3
a.
b.
c.
d.
8. Write down the lewis structure of the following odd electron species
a. NO2 b. CH3 c. ClO2 d. NO3 e. CH2 CHCH2
ClF2
PF5
BrF5
ClF2
9. Explain why a)
and
have different shapes. b)
and
have different F Cl F bond angles ?
10. Write all the isoelectronic structures of

CO2

11. Write down the Lewis structure of all possible isomers of

contains a benzene ring.

C7H9N

, which

12. Estimate the bond angles which are marked in the following molecule.

13. In each pair identify the one with a weaker C H bond

a.

CH3Cl

b.

C2H3CH2 - H

&

CH3NO2

&

C2H5CH2 - H

c.

(CH3)3 C - H

&

(CH3)2 CH - H

14. Write down the Lewis structures of

2SO3
a.
2SO
b. 2 3
2S2O8
c.
H PO
d. 3 4
H3PO3
e.
2Cr2O7
f.
CrO5
g.
15. For each of the following species, draw MO diagrams to find out the bond
order and the number of unpaired electrons: N2 , H2 -, B2 , C2 +, O22- and
F2+.
16. Assuming that the MO energy level diagrams for homonuclear and hetero
nuclear diatomic species are similar, draw MO diagrams to find out the
bond order and the number of unpaired electrons for each of the
following species: NO, NO+, CO, CN, CO+ , CN- ,CN+ , BN.
17. In each of the following cases write down the various contributing
resonance structures
CHCl
CH2
a.
BNH
b. 3 3 6 (inorganic benzene)
c. methanoic acid
d.

CH2CH(CHO)

e.

C6H5N2

_
CNO
f.
CH2CHCH2CHO
g.

18. Keeping the same atomic connections and moving only electrons write a
more stable Lewis structure for each of the following?
H
H

a. H

H
+
O

C
O

b.

H
+
C
c. H
H

d.

C
H

+
N

C
H

NCNC(NH2)2
19. Show the C N skeleton structure of dicyandiamide
and
label the various bond angles, label also the & bonds in the skeleton.
And indicate each type of orbital overlaps which produce these bonds.

20.Replace the highlighted atoms with another atom to obtain corresponding

isoelectronic species :
(CH3)3 CN
a.
BF4
b.
(C2H5)3 N
c.
(two answers)
d.

C2H5O

e.

(CH3)2O

f.

CH2

(two answers)

N CH3