Assignment: Organic Chemistry 2 Marks: 100
Organic Concepts Due Date: 28 August 2025
1.0 Isonitriles (A) are an important class of compounds because of the versatile reactivity of the
functional group, enabling the preparation of numerous new compounds and natural
products. Isonitriles can be converted to isonitrile dihalides (B), which represents a useful
procedure for temporarily hiding the reactivity of an isonitrile.
1.1 Identify the hybridization state for each highlighted atom in A. (1)
1.2 One of the carbon atoms in A exhibits a lone pair. In what type of atomic orbital does this
lone pair reside? (1)
1.3 Predict the C−N−C bond angle in compound A. (1)
1.4 Identify the hybridization state for each highlighted atom in B. (1)
1.5 The nitrogen atom in B exhibits a lone pair. In what type of atomic orbital does this lone pair
reside? (1)
1.6 Predict the C−N−C bond angle in compound B. (1)
2.1 On the basis of MO theory, explain why Li2 molecules can exist but Be2 molecules cannot.
Could the ion Be2+ exist? (4)
3.1 Determine the relationship between the two structures below. Are they resonance
structures or are they constitutional isomers? (6)
4.1 A mixture of sulfuric acid and nitric acid will produce small quantities of the nitronium ion
(NO2+):
Does the nitronium ion have any significant resonance structures? Why or why not? (3)
1
, 5.1 Consider the following two compounds:
5.1.1 Identify which of these two compounds has greater resonance stabilization. (6)
5.1.2 Would you expect compound C (below) to have a resonance stabilization that is more similar
to compound A or to compound B? (6)
6.0 Tropolone (1) is a compound that is both fairly acidic and fairly basic. It is acidic because it is
capable of losing a proton (H+) to form a relatively stable anion (2), while it is basic because
of its ability to receive a proton to form cation 3:
6.1 Draw all significant resonance structures of anion 2 and of cation 3 and explain why each of
these ions is stabilized. (8)
6.2 In compound 1, the bond lengths for the C—C bonds vary greatly and alternate in length
(long, short, long, etc.). But in ions 2 and 3, the lengths of the bonds are similar. Explain. (3)
6.3 The intramolecular hydrogen bonding interaction in 3 is significantly diminished in
comparison to 1. Explain. (3)
2
Organic Concepts Due Date: 28 August 2025
1.0 Isonitriles (A) are an important class of compounds because of the versatile reactivity of the
functional group, enabling the preparation of numerous new compounds and natural
products. Isonitriles can be converted to isonitrile dihalides (B), which represents a useful
procedure for temporarily hiding the reactivity of an isonitrile.
1.1 Identify the hybridization state for each highlighted atom in A. (1)
1.2 One of the carbon atoms in A exhibits a lone pair. In what type of atomic orbital does this
lone pair reside? (1)
1.3 Predict the C−N−C bond angle in compound A. (1)
1.4 Identify the hybridization state for each highlighted atom in B. (1)
1.5 The nitrogen atom in B exhibits a lone pair. In what type of atomic orbital does this lone pair
reside? (1)
1.6 Predict the C−N−C bond angle in compound B. (1)
2.1 On the basis of MO theory, explain why Li2 molecules can exist but Be2 molecules cannot.
Could the ion Be2+ exist? (4)
3.1 Determine the relationship between the two structures below. Are they resonance
structures or are they constitutional isomers? (6)
4.1 A mixture of sulfuric acid and nitric acid will produce small quantities of the nitronium ion
(NO2+):
Does the nitronium ion have any significant resonance structures? Why or why not? (3)
1
, 5.1 Consider the following two compounds:
5.1.1 Identify which of these two compounds has greater resonance stabilization. (6)
5.1.2 Would you expect compound C (below) to have a resonance stabilization that is more similar
to compound A or to compound B? (6)
6.0 Tropolone (1) is a compound that is both fairly acidic and fairly basic. It is acidic because it is
capable of losing a proton (H+) to form a relatively stable anion (2), while it is basic because
of its ability to receive a proton to form cation 3:
6.1 Draw all significant resonance structures of anion 2 and of cation 3 and explain why each of
these ions is stabilized. (8)
6.2 In compound 1, the bond lengths for the C—C bonds vary greatly and alternate in length
(long, short, long, etc.). But in ions 2 and 3, the lengths of the bonds are similar. Explain. (3)
6.3 The intramolecular hydrogen bonding interaction in 3 is significantly diminished in
comparison to 1. Explain. (3)
2
