Test bank for introduction to organic chemistry 5th edition by brown

Test Bank for Introduction to Organic Chemistry 5th Edition by Brown
Full file at />Chapter 1 - Covalent Bonding and Shapes of Molecules
Package Title: Brown/Poon Test Bank
Course Title: Brown/Poon 5e
Chapter Number: 1

Question type: Multiple Choice

Section 1.1
Difficulty Level: Easy
1. Which is the electronic configuration that describes Mg2+?
a) 1s2, 2s2
b) 1s2, 2s2, 2p6
c) 1s2, 2s2, 2p6, 3s2
d) 1s2, 2s2, 2p6, 3s2, 3p6
Answer: b

Section 1.1
Difficulty Level: Easy
2. Which is the electronic configuration that describes a neutral carbon atom?
a) 1s2, 2s2, 2p5
b) 1s2, 2s2, 2p6, 3s2
c) 1s2, 2s2, 2p2
d) 1s2, 2s2, 2p6
Answer: c

Section 1.1
Difficulty Level: Easy
3. Which atom is described by the electronic configuration 1s22s22p63s23p3?
a) Mg
b) Al

c) Si
d) P
Answer: d

Section 1.1
Difficulty Level: Easy
4. Which atom is described by the electron configuration 1s22s22p63s23p5?
a) S
b) Se
c) Cl
d) Br
Answer: c

1

Full file at />

Test Bank for Introduction to Organic Chemistry 5th Edition by Brown
Full file at />Chapter 1 - Covalent Bonding and Shapes of Molecules

Section 1.1
Difficulty Level: Easy
5. A neutral carbon has how many valence electrons?
a) 2
b) 4
c) 6
d) 8

Answer: b

Section 1.1
Difficulty Level: Easy
6. A neutral oxygen has how many valence electrons?
a) 4
b) 5
c) 6
d) 7
Answer: c

Section 1.1
Difficulty Level: Easy
7. A neutral nitrogen has how many valence electrons?
a) 4
b) 5
c) 6
d) 7
Answer: b

Section 1.1
Difficulty Level: Medium
8. Which statement about orbitals is false?
a) Orbitals are regions of space where electrons are found.
b) Orbitals may contain up to two electrons each.
c) Orbitals are filled in order of decreasing energy.
d) Orbitals of equivalent energy are half filled before adding two electrons to any one of them.
Answer: c

2

Full file at />

Test Bank for Introduction to Organic Chemistry 5th Edition by Brown
Full file at />Chapter 1 - Covalent Bonding and Shapes of Molecules

Section 1.2
Difficulty Level: Easy
9. Which atom is described by the Lewis structure

A ?

a) C
b) P
c) Se
d) I
Answer: c

Section 1.2
Difficulty Level: Easy
10. Which atom is described by the Lewis structure

A ?

a) C
b) P
c) Se
d) I

Answer: a
Section 1.2
Difficulty Level: Medium

11. Which Lewis structures are correct?
HINT: Count the electrons around each atom in step 1 and check, whether the charges (or the absence of them) are
correct in step 2.

H
H

C

OH

H

H

H

C

C

O
H

H

O

O

H

H

O

C

H
I

II

III

IV

a) I
b) II
c) III
d) IV
Answer: a

3

Full file at />
O

H

Test Bank for Introduction to Organic Chemistry 5th Edition by Brown
Full file at />Chapter 1 - Covalent Bonding and Shapes of Molecules

Sections 1.2, 1.7
Difficulty Level: Medium
12. Which Lewis structures are correct?
HINT: Count the electrons around each atom in step 1 and check, whether the charges (or the absence of them) are
correct in step 2.

a)
b)
c)
d)

I, II
II, IV
III, IV
I, III

Answer: c

Section 1.2
Difficulty Level: Medium
13. Which functional groups have correct Lewis structures?

CH3
CH3

C

O

CH3
I

CH3
H

C

O
O

CH3

C

CH3
II

III

a) I, II
b) II, III
c) I, II, III
d) I, III

Answer: d

4

Full file at />
O

H


Test Bank for Introduction to Organic Chemistry 5th Edition by Brown
Full file at />Chapter 1 - Covalent Bonding and Shapes of Molecules

Section 1.2
Difficulty Level: Hard
14. Which is the correct Lewis structure for acetic acid (CH3CO2H)?

H

O

H

C

C

H

H

O H

I

H

O

C

C

H

H

H
O H

C

O
O

C

H H

O

O

H

C

C

H

II

H
III

IV

a) I
b) II
c) III
d) IV
Answer: d

Section 1.3
Difficulty Level: Medium
15. Using the VSEPR model, predict which atoms have bond angles of about 120°.

O
C
CH3

H

I

CH3OH

II

CH2

CH2

NH4Cl

III

IV

a) II, IV
b) I, IV
c) II, III
d) I, III

Answer: d

5

Full file at />
H

Test Bank for Introduction to Organic Chemistry 5th Edition by Brown
Full file at />Chapter 1 - Covalent Bonding and Shapes of Molecules

Section 1.3
Difficulty Level: Medium
16. Using the VSEPR model, predict which species have bond angles of about 109°.
HINT: Assume that the charges are correct. Add the missing lone pairs before applying the VSEPR theory!

NH3
I

CO2

H2O

II

III

H3O

+

O3

IV

V

a) I, III, IV
b) II, III, V
c) I, IV
d) III, IV, V

Answer: a

Section 1.3
Difficulty Level: Medium
17: Which of the atoms that are marked with an arrow have tetrahedral geometry?

O

CH3

O

OH

C
CH3

C
H

I
a)
b)
c)
d)

H

CH3
II

CH3
III

CH3

IV

I, II
II, IV
I, IV, V
II, II, V

Answer: b

6

Full file at />
N

O

CH3

C

CH3

OH
V


Test Bank for Introduction to Organic Chemistry 5th Edition by Brown
Full file at />Chapter 1 - Covalent Bonding and Shapes of Molecules

Sections 1.3, 1.5
Difficulty Level: Medium
18: Which of the atoms that are marked with an arrow are sp2-hybridized?

O

H3C

O

OH

C
CH3

H

C
H

I

CH3
II

CH3
III

N

O

CH3

CH3

C
CH3

OH

IV

V

a) I, II, III
b) I, II, IV
c) I, III, V
d) III, IV
Answer: c

Section 1.3
Difficulty Level: Hard

-

19. According to VSEPR model, what is your prediction for the arrangement of electron pairs for CH3 ?
a) linear
b) tetrahedral
c) bent
d) trigonal

Answer: b

Section 1.4
Difficulty Level: Easy
20. Arrange the bonds in increasing order of ionic character (least first).
C-C
I

Na-O
II

C-N
III

O-H
IV

a) III, I, IV, II, V
b) V, III, I, II, IV

c) I, V, III, IV, II
d) I, III, V, IV, II
Answer: d

7

Full file at />
C-O
V


Test Bank for Introduction to Organic Chemistry 5th Edition by Brown
Full file at />Chapter 1 - Covalent Bonding and Shapes of Molecules
Section 1.4
Difficulty Level: Easy
21. Nitrogen has a negative formal charge in which of the following compounds?
a) NaNH2
b) N2
c) NH4Cl
d) HCN
Answer: a

Section 1.4
Difficulty Level: Easy
22. What is the formal charge of oxygen in H3O+?
a) –1
b) 0
c) +1
d) +2
Answer: c

Section 1.4
Difficulty Level: Medium
23. Which compounds contain both covalent and ionic bonds?
CH3OH
I

Na2CO3
II

NH4Cl
III

NaCl
IV

a) I, II
b) II, IV
c) I, II, IV
d) II, III

Answer: d

Section 1.4
Difficulty Level: Medium
24. Which of these molecules are polar?
HINT: look for the presence of at least one polar covalent bond in these molecules!

NH3

CO2

H2O

I

II

III

a)
b)
c)
d)

I, IV
I, III
II, III, IV
III, IV, V

Answer: b
8

Full file at />
CH4

Br2

IV

V


Test Bank for Introduction to Organic Chemistry 5th Edition by Brown
Full file at />Chapter 1 - Covalent Bonding and Shapes of Molecules

Section 1.4
Difficulty Level: Medium
25. Which of these molecules are polar?
HINT: look for the presence of at least one polar covalent bond in these molecules!

O
CH2

CH2
I

C
H

H

CH2Cl2

II

CH3
IV

III

CH3

CH3OH
V

a) III, IV, V
b) I, IV
c) II, III, V
d) I, III
Answer: c

Section 1.4
Difficulty Level: Medium
26. What is the formal charge of indicated carbon in the following molecule?

O
CH3 C
H
a) –2
b) –1
c) 0
d) +1
Answer: b

9

Full file at />

Test Bank for Introduction to Organic Chemistry 5th Edition by Brown

Full file at />Chapter 1 - Covalent Bonding and Shapes of Molecules
Section 1.4
Difficulty Level: Hard
27. Using the VSEPR model, predict which molecules have bond angles of about 109°.

F
CH2

CH2

CH2

I

O

CH3

II

N

C

O

Cl

III

C

CH3
F

HO

C

Cl

CH3

IV

V

CH3

a) II, IV
b) I, II, III
c) III, IV, V
d) II, III, IV

Answer: c

Section 1.4
Difficulty Level: Hard
28. Using the VSEPR model, predict which molecules have bond angles of about 120°.

F
CH2

CH2

I

CH2

O

II

CH3

N

C

III

O

Cl

C

CH3
F

CH3

IV

V

Answer: b

Section 1.5
Difficulty Level: Medium
29. Which statement about contributing structures is false?
a) All contributing structures must have the same number of valence electrons.
b) All contributing structures must obey the rules of covalent bonding.
c) The position of nuclei may change.
d) Third period atoms may have up to 18 electrons around them.

10

Full file at />
C

Cl

a) I, II, IV
b) I, II, III
c) III, IV, V
d) II, III, IV

Answer: c

HO

CH3


Test Bank for Introduction to Organic Chemistry 5th Edition by Brown
Full file at />Chapter 1 - Covalent Bonding and Shapes of Molecules
Section 1.5
Difficulty Level: Hard
30. Which of the following are pairs of contributing structures?

I

O
CH3

II

CH2

III

CH2 CH

IV

CH3

CH3

N

CH2
OH

CH2

O

CH2

CH2

C

N

O

O

CH CH2

C

O

a) II, IV
b) I, II, III
c) III, IV

d) II, III, ,IV
Answer: c

Section 1.6
Difficulty Level: Medium
31. The carbon has the correct orbital hybridization in which structures?

CH2

O

CH2

CH2

sp2

sp
I

II

CH4

CH

sp2

sp

III

IV

a) II, IV, V
b) II, III, IV
c) I, II, III
d) I, IV, V
Answer: a

Section 1.6
11

Full file at />
N

O

C
sp
V

O


Test Bank for Introduction to Organic Chemistry 5th Edition by Brown
Full file at />Chapter 1 - Covalent Bonding and Shapes of Molecules
Difficulty Level: Medium
32. What are the correct orbital hybridizations for carbon in the following species?
HINT: Add a lone pair if the charge of the molecule suggests it!

CH3

CH4

CH3

a) CH3+ is sp-hybridized
b) CH3- is sp2-hybridized
c) CH4 is sp2-hybridized
d) CH3- is sp3-hybridized
Answer: d

Section 1.7
Difficulty Level: Easy
33. Which of the following compounds is a tertiary (3°) alcohol?

CH3

CH3

CH OH

CH3

C

CH3

CH3

I

II

CH3
OH

CH3

OH

C

CH2

CH3
III

Answer: b

Section 1.7

12

OH

CH CH
CH3

a) I
b) II
c) III
d) IV

Full file at />
CH3

CH3
IV


Test Bank for Introduction to Organic Chemistry 5th Edition by Brown
Full file at />Chapter 1 - Covalent Bonding and Shapes of Molecules
Difficulty Level: Medium
34. Which compounds are classified correctly?
HINT: Assume that the charges are correct. Add the missing lone pairs!

O

O
CH3

C
CH3

H

OH

H

C
CH3

CH3

N
CH3

alcohol

aldehyde

ketone

amine

I

II

III

IV

O

CH3

C
CH3

OH

carboxylic acid

V

a) III, IV, V
b) II, III, IV
c) I, III, V
d) I, III, IV
Answer: a

Section 1.7
Difficulty Level: Medium
35. Which of the three molecules testosterone, methadone and hydrocodone contains a ketone?
testosterone

methadone
N

OH
O

H
H

hydrocodone

N

H
O

O
I

II

III

a) I,II
b) III
c) II,III
d) I, II, III
Answer: d

13

Full file at />
O

O


Test Bank for Introduction to Organic Chemistry 5th Edition by Brown
Full file at />Chapter 1 - Covalent Bonding and Shapes of Molecules

Section 1.7

Difficulty Level: Medium
36. Which of the three molecules testosterone, methadone and hydrocodone contains an amine?

testosterone

methadone
N

OH
O

H
H

hydrocodone
N

H
O

O
I

II

O

O

III

a) I,II
b) III
c) II,III
d) I, II, III

Answer: c

Section 1.7
Difficulty Level: Medium
37. Which of the three molecules testosterone, methadone and hydrocodone contains a hydroxyl group.

testosterone

methadone
N

OH
O

H
H

hydrocodone
N

H
O

O

I

II

III

a) I
b) I, III
c) II,III
d) I, II, III

Answer: a

Section 1.7
14

Full file at />
O

O


Test Bank for Introduction to Organic Chemistry 5th Edition by Brown
Full file at />Chapter 1 - Covalent Bonding and Shapes of Molecules
Difficulty Level: Medium
38. Which of the three molecules aspirin, paracetamol and ibuprofen contains a carboxyl group?

aspirin

paracetamol

ibuprofen

O
OH

O

O

HO

O
O

N
H

OH
I

II

III

a) I
b) I, III
c) II,III
d) I, II, III
Answer: b

Section 1.7
Difficulty Level: Hard
39. What is the correct structure for the aldehyde, which has the formula C4H8O?

O

OH
CH3

CH

CH CH2

CH3

C CH2 CH3
II

I
O
CH3 CH2 CH2 CH
III

CH2 CH
IV

a) I
b) II
c) III

d) IV
Answer: c

15

Full file at />
CH2 O

CH3


Test Bank for Introduction to Organic Chemistry 5th Edition by Brown
Full file at />Chapter 1 - Covalent Bonding and Shapes of Molecules
Question type: Fill-in-the-Blank

Section 1.1
Difficulty Level: Easy
40. The spins of two electrons in the same orbital must be _______ .

Answer: paired

Section 1.1
Difficulty Level: Easy
41. Outer shell electrons are called _________ electrons.
Answer: valence

Section 1.1
Difficulty Level: Easy
42. ______ is the number of valence electrons for a neutral sulfur atom.
Answer: 6

Section 1.1
Difficulty Level: Easy
43. ______ is the number of valence electrons for a neutral bromine atom.
Answer: 7

Section 1.1
Difficulty Level: Easy
44. The tendency of an element to react such that it achieves a noble gas configuration is called
the ______ ______. (Sec. 1.1, EASY)
Answer: octet rule

Section 1.4
Difficulty Level: Medium
45. The most polar bond in the following molecule is __________.

F

H

OH H

C

C

C

H

H

H

NH2

Answer: C-F

16

Full file at />

Test Bank for Introduction to Organic Chemistry 5th Edition by Brown
Full file at />Chapter 1 - Covalent Bonding and Shapes of Molecules
Section 1.4
Difficulty Level: Medium
46. A __________ bond is characterized by the unequal sharing of electrons.
Answer: polar covalent

Section 1.7
Difficulty Level: Medium
47. The following molecule contains the _________ and __________ functional groups.

O

OH
Answer: hydroxyl and carbonyl

Section 1.7
Difficulty Level: Medium

48. The following molecule contains the _________ and __________ functional groups.

NH2

OH
O
Answer: primary amino and carboxyl

Section 1.7
Difficulty Level: Medium
49. Functional groups undergo the same type of __________ in whatever compound they are found.
Answer: reactions

Section 1.7
Difficulty Level: Medium
50. ______________ are the basis for compound nomenclature.

Answer: Functional groups

17

Full file at />

Test Bank for Introduction to Organic Chemistry 5th Edition by Brown
Full file at />Chapter 1 - Covalent Bonding and Shapes of Molecules
Question type: True/False
Section 1.1
Difficulty Level: Easy
51. Each shell can hold two electrons.
Answer: False

Section 1.1
Difficulty Level: Medium
52. Orbitals make up the majority of the mass of an atom.
Answer: False

Section 1.2
Difficulty Level: Easy
53. An neutral atom that has gained electrons is called an anion.
Answer: True

Section 1.2
Difficulty Level: Easy
54. Ionic bonds are characterized by the unequal sharing of electrons.
Answer: False

Section 1.2
Difficulty Level: Medium
55. Atoms of the group 7A elements react by losing an electron to achieve a noble gas configuration.
Answer: False

Section 1.2
Difficulty Level: Medium
56. Atoms of the group 2A elements react by losing two electrons to achieve a noble gas configuration.
Answer: True

Section 1.2
Difficulty Level: Medium
57. Carbon atoms usually react by gaining 4 electrons to achieve a noble gas configuration.

Answer: False

18

Full file at />

Test Bank for Introduction to Organic Chemistry 5th Edition by Brown
Full file at />Chapter 1 - Covalent Bonding and Shapes of Molecules
Section 1.4
Difficulty Level: Medium
58.

CH3CH2CH2CH2CH2OH

is a polar molecule.

Answer: True

Section 1.4
Difficulty Level: Medium
59.

CH3ONa

contains only polar covalent bonds.

Answer: False

Section 1.7
Difficulty Level: Medium

60. The following molecule is an example of a secondary amine.

CH3
HC NH2
CH3

Answer: False

19

Full file at />