40 questions (4.5 point each) in total of 180 points
Q1 (CH1). Which one of the below is the correct Lewis structure? (4 pts)
A B C D
Q2 (CH1) Based on VSEPR model, what is your prediction for the electronic configuration
and the molecular shape of CH3⊖?
A. sp2, trigonal # of σ bonds = 3
H
B. sp2, tetrahedral # of lone pairs = 1 H H
C. sp3, trigonal Steric number = 4 à sp3, tetrahedral
D. sp3, tetrahedral
Q3 (CH2). The structure shown below is caRein. Select the correct answer (4 pts).
O CH3
H 3C 4
1N C N
C H
C N
O N
2 3
CH3
A. The lone pairs on all four nitrogen atoms are all delocalized.
B. The lone pairs on all four nitrogen atoms are all delocalized.
C. Delocalized lone pairs on N1, N2, N3; Localized lone pair on N4.
D. Delocalized lone pairs on N1, N2, N4; Localized lone pair on N3.
Answers A and B are the same. We did not catch this error.
,Q4 (CH2). Select one structure that shows the correct resonance hybrid of the compound
in box.
δ- δ- δ+ δ-
δ- δ+ δ+ δ+ δ-
δ-
δ- δ+ δ- δ+
A B C D E
Q5 (CH3). Rank the indicated protons in increasing order of acidity.
I H
H III
O H
II
A. Lease acidic II < I < III Most acidic
B. Least acidic II < III < I Most acidic
C. Least acidic I < III < II Most acidic
D. Least acidic I < II < III Most acidic
E. Least acidic III < II < I Most acidic
Q6 (CH3) Which solvent should be used for the reaction below?
H
H + N + N
O O
OH
OH OH
Tetrahydrofuran Ethanol acetic acid tert-butanol
(THF)
A B C D
, Q7 (CH3) Rank the following compounds in increasing order of acidity.
Cl O O
O O
OH Cl OH
Cl OH Cl OH Cl Cl Cl
I II III IV
A. I < II < III < IV
B. I < III < II < IV
C. I < II < IV < III
D. III < IV < II < I
Q8 (CH3) Which of the following compounds will be extracted into a pH 1 aqueous
solution?
OH COOH CH2OH NH2 NH2
I II III IV V
A. I and II
B. I, II and III
C. II
D. IV and V. These compounds will be protonated at pH 1.
Q9 (CH4). Select the correct IUPAC name of the compound below (4 pts).
A. 2,2,3-trimethyl-3-ethyl-5-propylnonane
B. 3-ethyl-2,2,3-trimethyl-5-propylnonane
C. 3-tert-butyl-3-methyl-5-propylnonane
D. 3-methyl-5-propyl-3-tert-butylnonane
Q1 (CH1). Which one of the below is the correct Lewis structure? (4 pts)
A B C D
Q2 (CH1) Based on VSEPR model, what is your prediction for the electronic configuration
and the molecular shape of CH3⊖?
A. sp2, trigonal # of σ bonds = 3
H
B. sp2, tetrahedral # of lone pairs = 1 H H
C. sp3, trigonal Steric number = 4 à sp3, tetrahedral
D. sp3, tetrahedral
Q3 (CH2). The structure shown below is caRein. Select the correct answer (4 pts).
O CH3
H 3C 4
1N C N
C H
C N
O N
2 3
CH3
A. The lone pairs on all four nitrogen atoms are all delocalized.
B. The lone pairs on all four nitrogen atoms are all delocalized.
C. Delocalized lone pairs on N1, N2, N3; Localized lone pair on N4.
D. Delocalized lone pairs on N1, N2, N4; Localized lone pair on N3.
Answers A and B are the same. We did not catch this error.
,Q4 (CH2). Select one structure that shows the correct resonance hybrid of the compound
in box.
δ- δ- δ+ δ-
δ- δ+ δ+ δ+ δ-
δ-
δ- δ+ δ- δ+
A B C D E
Q5 (CH3). Rank the indicated protons in increasing order of acidity.
I H
H III
O H
II
A. Lease acidic II < I < III Most acidic
B. Least acidic II < III < I Most acidic
C. Least acidic I < III < II Most acidic
D. Least acidic I < II < III Most acidic
E. Least acidic III < II < I Most acidic
Q6 (CH3) Which solvent should be used for the reaction below?
H
H + N + N
O O
OH
OH OH
Tetrahydrofuran Ethanol acetic acid tert-butanol
(THF)
A B C D
, Q7 (CH3) Rank the following compounds in increasing order of acidity.
Cl O O
O O
OH Cl OH
Cl OH Cl OH Cl Cl Cl
I II III IV
A. I < II < III < IV
B. I < III < II < IV
C. I < II < IV < III
D. III < IV < II < I
Q8 (CH3) Which of the following compounds will be extracted into a pH 1 aqueous
solution?
OH COOH CH2OH NH2 NH2
I II III IV V
A. I and II
B. I, II and III
C. II
D. IV and V. These compounds will be protonated at pH 1.
Q9 (CH4). Select the correct IUPAC name of the compound below (4 pts).
A. 2,2,3-trimethyl-3-ethyl-5-propylnonane
B. 3-ethyl-2,2,3-trimethyl-5-propylnonane
C. 3-tert-butyl-3-methyl-5-propylnonane
D. 3-methyl-5-propyl-3-tert-butylnonane
