Organic Chemistry 2nd Edition Test Bank by David R. Klein

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Topic: Molecular Representation
Section: 2.1
Difficulty Level: Easy
1. What is the molecular formula for the following compound?
H C
H
H
C
H

H
O C
H

H
C
H

H
H

A) C2H6O
B) C4H6O
C) C4H10O
D) C2H4O
E) None of these
Ans: C
Topic: Molecular Representation
Section: 2.1
Difficulty Level: Easy
2. Which of the following compounds have a molecular formula of C2H6O?
CH3OCH3 CH3CH2OCH3 CH3CH2OH CH3CHOHCH3
I II

III IV

A) I
B) II
C) III
D) IV
E) Both I & III
Ans: E
Topic: Molecular Representation
Section: 2.1
Difficulty Level: Easy

3. Which of the following is the correct condensed structure for the following compound?

H
C
C
C
O
H

H H

H C
H H
H
H H

A) CH3CH3CH2OH
B) CH3CH2CH2OH
C) (CH3)2CHCH2OH
D) CH3CH2CH2OCH3
E) CH3C2H3CH3OH
Ans: C
Topic: Molecular Representation
Section: 2.1
Difficulty Level: Easy
4. Which of the following is the correct condensed structure for the following compound?

H C C C C
H

H
H

O
H

H
C
H

H
C H
Cl

H
H

H

H

A) CH3CHOHCH2CHClCH3
B) CH3CHOH(CH2)2CHClCH3
C) (CH3)2CHOHCH2CH2Cl
D) CH3CHCH2CH2OHCH3CHCl
E) CH3C2H4CH3OHCl
Ans: B
Topic: Molecular Representation
Section: 2.1
Difficulty Level: Medium

5. Which of the following is the correct condensed structure for the following compound?

A) CH2=CH(CH2)3C(CH3)3
B) CH(CH2)4C(CH3)3
C) (CH3)2CH(CH2)4CH3
D) CH2CH(CH2)3C(CH3)3
E) (CH)3(CH2)3C(CH3)3
Ans: A
Topic: Molecular Representation
Section: 2.1
Difficulty Level: Medium
6. Which of the following is the correct condensed structure for the following compound?

C C C C C
H

H
C
H

H
C C
H

H
C

C
H
H

H
H
H
H
H
H H

H

H
H

A) CH3C2(CH2)3C(CH3)3
B) CH3CC(CH2)3C(CH3)2CH3
C) (CH3)3C2(CH2)3CH3
D) CH3CC(CH2)3C(CH3)3
E) CH3CC(CH2)3C(CH3)3
Ans: D
Topic: Molecular Representation
Section: 2.1
Difficulty Level: Medium

7. Which of the following is the correct condensed structure for the following compound?

C C C C H
H

Br
C
H

H
C C
H

H
C

C
H
H

H
H
H
H
H
H H

H
C H

H
H
H H

A) CH3C(CH3)2(CH2)2(CH)BrC(CH3)2
B) CH3CH3CH3C(CH2)2C(CH3)2CHBr
C) (CH3)3C(CH2)3BrCHCH3CH3
D) CH3CH3CH3C(CH2)2CHBrCHCH3CH3
E) (CH3)3C(CH2)2CHBrCH(CH3)2
Ans: E
Topic: Molecular Representation
Section: 2.1
Difficulty Level: Hard
8. Provide correct condensed structure for the following compound.

C C O C C C
H

H
C C
H

H
C

C
H
H

H
H
H
H
H
H H

H
C H

H
C
H H

H
H

H
H H
H

Ans: (CH3)3C(CH2)2OCH(CH2CH3)2
Topic: Molecular Representation
Section: 2.1
Difficulty Level: Hard
9. Provide correct condensed structure for the following compound.

C C C C H
H

H
C
H

H
C N
H

C H
H
H

H
H
H
H

H
C H

H
H
H H

Ans: (CH3)2N(CH2)3CH(CH3)2
Topic: Molecular Representation
Section: 2.1
Difficulty Level: Easy

10. Which of the following is the correct molecular formula for (CH3CH2)4C?
A) C8H20
B) C5H20
C) C9H20
D) C6H5
E) C3H20
Ans: C
Topic: Molecular Representation
Section: 2.1
Difficulty Level: Easy
11. Which of the following is the correct Lewis structure for CH3(CH2)2NH2?
H C
H
H
C
H

H
N H
H

C C
H
H
C
H

H
N H

H
H
H H

C C
H
H
C
H

H
N H

H
H
H H

CH3CH2CH2NH2

I II

III

IV

A) I
B) II
C) III
D) IV
E) Both II & III
Ans: C
Topic: Molecular Representation
Section: 2.1
Difficulty Level: Easy
12. Which of the following is the correct Lewis structure for CH3(CH2)2OH?
H C
H
H
C
H

H
O H C C
H
H
C
H

H
O H

H
H
H

C C
H
H
C
H

H
O H

H
H
H

CH3CH2CH2OH

I II

III

IV

A) I
B) II
C) III
D) IV
E) Both II & III
Ans: B
Topic: Molecular Representation
Section: 2.1
Difficulty Level: Easy

13. Which of the following is the correct Lewis structure for (CH3)2CHCH2OH?

C C
H

H
C
H
H
C O
H

H
H

H

H
H C H
H

H
C
H
H
C O
C

H
H
H
H H

H C
H
H
C
H
C
C O
H
H
H
H
H H

H C
H
H
C
H
C
C OH
H
H
H
H H

I II

III IV

A) I
B) II
C) III
D) IV
E) Both III & IV
Ans: C
Topic: Molecular Representation
Section: 2.1
Difficulty Level: Medium
14. Which of the following is the correct Lewis structure for (CH3)3C(CH2)2NHCH3?

H C
H
H
C
C
C
H H

H
H H
C
H
H
C
H
H
N C
H
H
H
H
H

C C
H
H
C
C
H

H
H H
C
H
H
C
H
H
N C
H
H
H
H H
H
H

H C
H
H
C
C
H
H H
C
C
H
C
H
H
N C
H
H
H
H H
H
H H

C C
H
C
C
C
H

H
H H
C
H
H
C
H
H
N H
H

H
H
H
H
H H

H C
H
H
C
C
H
H H
C
C
H
C
H
H
N CH3
H
H
H
H H

I II

III

IV

V

A) I
B) II
C) III
D) IV
E) V
Ans: D
Topic: Molecular Representation
Section: 2.1
Difficulty Level: Medium

15. Draw the Lewis structure for CH3CC(CH2)3C(CH3)3.
Ans:

C C C C C
H

H
C
H

H
C C
H

H
C

C
H
H

H
H
H
H
H
H H

H

H
H

Topic: Molecular Representation
Section: 2.1
Difficulty Level: Hard
16. Draw the Lewis structure for (CH3)3C(CH2)2OCH(CH2CH3)2.
Ans:

C C O C C C
H

H
C C
H

H
C

C
H
H

H
H
H
H
H
H H

H
C H

H
C
H H

H
H

H
H H
H

Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Easy
17. Which of the following bond-line structures are of the same compound?

I

II III

IV

A) I & II
B) II & III
C) III & IV
D) II & IV
E) None of these
Ans: D
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Easy

18. Which of the following bond-line structures are of the same compound?

I II III IV

A) I & III
B) II & III
C) III & IV
D) II & IV
E) None of these
Ans: A
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Easy
19. How many H atoms are connected to the indicated carbon atom?

A) one
B) two
C) three
D) four
E) none
Ans: E
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Easy
20. How many H atoms are connected to the indicated carbon atom?

A) one
B) two
C) three
D) four
E) none
Ans: A
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Easy

21. How many H atoms are connected to the indicated carbon atom?

A) one
B) two
C) three
D) four
E) none
Ans: B
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Easy
22. How many H atoms are connected to the indicated carbon atom?

A) one
B) two
C) three
D) four
E) none
Ans: A
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Easy
23. How many H atoms are connected to the indicated carbon atom?

A) one
B) two
C) three
D) four
E) none
Ans: E
Topic: Bond Line Structure
Section: 2.2

Difficulty Level: Easy
24. For the following transformation how many H atoms are added or lost?
A) Added one
B) Added two
C) Lost one
D) Lost two
E) No change
Ans: D
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Easy
25. For the following transformation how many H atoms are added or lost?
O OH

A) Added one
B) Added two
C) Lost one
D) Lost two
E) No change
Ans: B
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Easy
26. For the following transformation how many H atoms are added or lost?
A) Added one
B) Added two
C) Lost one
D) Lost two
E) No change
Ans: E
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Easy

27. For the following transformation how many H atoms are added or lost?

O O
OH

A) Added one
B) Added two
C) Lost one
D) Lost two
E) No change
Ans: E
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Medium
28. For the following transformation how many H atoms are added or lost?

OH
A) Added one
B) Added two
C) Lost one
D) Lost two
E) No change
Ans: D
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Medium

29. For the following transformation how many H atoms are added or lost?

A) Added one
B) Added two
C) Lost one
D) Lost two
E) No change
Ans: E
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Easy
30. Which of the following is the correct Lewis structure for the following compound?
O

H C
H

H
C
O

H C
H

H
C H
H
O

H C
H

H
C
O

H
H C
H

H
C
O

O

I II III IV

A) I
B) II
C) III
D) IV
E) None of these
Ans: B
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Easy

31. Which of the following is the correct bond-line structure for (CH3)4C?

I II

III IV

A) I
B) II
C) III
D) IV
E) None of these
Ans: C
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Easy
32. Which of the following is the correct bond-line structure for (CH3)2CHCH2CH3?

I II

III IV

A) I
B) II
C) III
D) IV
E) None of these
Ans: A
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Medium
33. Which of the following is the correct bond-line structure for (CH3)2CHCH2C(CH3)3?

I II III IV
A) I
B) II
C) III
D) IV
E) None of these
Ans: B
Topic: Bond Line Structure
Section: 2.2

Difficulty Level: Medium
34. Which of the following is the correct bond-line structure for CH3CC(CH2)2CH(CH3)2?

I II

III

IV

A) I
B) II
C) III
D) IV
E) None of these
Ans: D
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Medium
35. Which of the following is the correct bond-line structure for
CH3CHOH(CH2)2CH(CH2CH3)2?

I

II III IV
OH

O O

OH

O

V

A) I
B) II
C) III
D) IV
E) V
Ans: B
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Medium
36. Draw a bond-line structure for CH3CH2O(CH2)2CH(CH3)2.
Ans:

O
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Hard

37. Draw a bond-line structure for (CH3)2N(CH2)3CH(CH3)2.
Ans:
N

Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Hard
38. Draw a bond-line structure for CH3CC(CH2)3C(CH3)2CH2OCH3.
Ans:

O

Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Hard
39. Draw a bond-line structure for each constitutional isomer with a molecular formula of
C2H4O.
Ans:
O O

O
H

Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Hard
40. Draw a bond-line structure for each constitutional isomer with a molecular formula of
C3H8O.
Ans:
OH

OH O

Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Hard

41. Provide a condensed structure for the following compound.

Ans: (CH3)3CCH2CH(CH2CH3)(CH2)2CH(CH3)CH2CH3
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Hard
42. Provide a condensed structure for the following compound.

NH2

Ans: (CH3)3C(CH2)2CH(NH2)CH=CHCH3
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Hard
43. Draw a bond-line structure for each constitutional isomer with molecular formula
C4H10O.
Ans:

OH

OH

OH OH

O

O O

Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Hard

44. Draw a bond-line structure for each constitutional isomer with molecular formula
C4H11N.
Ans:

NH2

NH2

NH2 NH2

H
N

N
H

N
H

N

Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Medium
45. Naproxen, sold under the trade name Aleve, has the following structure. What is the
molecular formula for naproxen?

O

O
OH

Ans: C14H14O3
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Hard
46. AZT, used in the treatment of AIDS, has the following structure. What is the molecular
formula for AZT?

N NH
O

O
O

N3
HO

Ans: C10H13N5O4
Topic: Bond Line Structure
Section: 2.2
Difficulty Level: Hard

47. Capsaicin, found in peppers, has the following structure. What is the molecular formula
for capsaicin?

OH
O
H
N
O

Ans: C18H27NO3
Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Easy
48. Which of the following compounds contain an alcohol functional group?

O OH

NH2

I II

III

IV

A) I
B) II
C) III
D) IV
E) None of these
Ans: C
Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Easy
49. Which of the following compounds contain an alkene functional group?
NH2

I

II

III

IV

A) I
B) II
C) III
D) IV
E) None of these
Ans: A
Topic: Identifying Functional Groups
Section: 2.3

Difficulty Level: Easy
50. Which of the following compounds contain an amine functional group?

O OH

NH2

I II

III

IV

A) I
B) II
C) III
D) IV
E) None of these
Ans: D
Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Easy
51. Which of the following compounds contain a ketone functional group?

HO
O

O
O

I II

III IV

O

O

A) I
B) II
C) III
D) IV
E) All of these
Ans: A
Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Easy

52. Which of the following compounds contain an aromatic ring?

I II III IV
O

A) I
B) II
C) III
D) IV
E) Both III & IV
Ans: C
Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Easy
53. Which of the following compounds contain an ester functional group?

I II III

IV

O
O

N
O

N O

A) I
B) II
C) III
D) IV
E) Both I & IV
Ans: A
Topic: Identifying Functional Groups
Section: 2.3
Difficulty Level: Easy
54. Which of the following compounds contain an amide functional group?

I II III

IV

O
O

N
O

N

C
N

A) I
B) II
C) III
D) IV
E) Both II & III
Ans: B
Topic: Identifying Functional Groups
Section: 2.3