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Sample Test

Organic Chemistry, 6e (Smith)

Chapter 3   Introduction to Organic Molecules and Functional Groups

 

1) Which of the following lists contains common heteroatoms found in organic molecules?

1.   A) N, O, S, P, Cl

2.   B) Na, O, S, P, Cl

3.   C) Na, Mg, S, N, Cl

4.   D) Na, Mg, O, N, Cl

 

Answer:  A

Difficulty: 1 Easy

Section:  03.01

Topic:  Functional Groups

Bloom’s:  2. Understand

Chapter:  03

Accessibility:  Keyboard Navigation

 

2) Why do heteroatoms confer reactivity on a particular molecule?

1.   A) Because they have lone pairs and create electron-rich sites on carbon.

2.   B) Because they have lone pairs and create electron-deficient sites on carbon.

3.   C) Because they are electronegative and act as electrophiles.

4.   D) Because they are electropositive and act as nucleophiles.

 

Answer:  B

Difficulty: 1 Easy

Section:  03.01

Topic:  Functional Groups

Bloom’s:  2. Understand

Chapter:  03

Accessibility:  Keyboard Navigation

 

3) Why do π bonds confer reactivity on a particular molecule?

1.   A) Because π bonds are difficult to break in chemical reactions.

2.   B) Because π bonds make a molecule an acid.

3.   C) Because π bonds are easily broken in chemical reactions.

4.   D) Because π bonds make a molecule an electrophile.

 

Answer:  C

Difficulty: 1 Easy

Section:  03.01

Topic:  Functional Groups

Bloom’s:  2. Understand

Chapter:  03

Accessibility:  Keyboard Navigation

 

 

 

4) Which of the following molecules contain the same functional groups?

 

 

1.   A) I, II, III

2.   B) I, II, IV

3.   C) II, III, IV

4.   D) I, III, IV

 

Answer:  D

Difficulty: 1 Easy

Section:  03.02

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

5) Which of the following molecules contain the same functional groups?

 

 

 

1.   A) I, II, IV

2.   B) I, II, III

3.   C) II, III, IV

4.   D) I, III, IV

 

Answer:  A

Difficulty: 1 Easy

Section:  03.02

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

 

 

6) Which of the following molecules are aliphatic hydrocarbons?

 

 

1.   A) I, II, III

2.   B) I and III

3.   C) II, III, IV

4.   D) II and IV

 

Answer:  B

Difficulty: 1 Easy

Section:  03.02

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

7) Which of the following molecules are aromatic hydrocarbons?

 

 

1.   A) I

2.   B) II

3.   C) III

4.   D) I and III

 

Answer:  D

Difficulty: 1 Easy

Section:  03.02

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

 

 

8) Which of the following correctly matches the molecules to the names of the functional group?

 

1.            CH3OH                 Carboxylic acid

2.           CH3CO2CH3            Ester

III.        CH3COCH3              Ketone

1.   IV.        H2CO                    Alcohol

 

1.   A) I and II

2.   B) III and IV

3.   C) II and III

4.   D) II and IV

 

Answer:  C

Difficulty: 1 Easy

Section:  03.02

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

Accessibility:  Keyboard Navigation

 

9) Which of the following correctly matches the molecules to the names of the functional group?

 

1.        CH3OCH3               Ether

2.       CH3CONH2          Amine

III.    CH3SH               Thiol

1.   IV.    CH3CHO           Alcohol

 

1.   A) I and II

2.   B) II and III

3.   C) III and IV

4.   D) I and III

 

Answer:  D

Difficulty: 1 Easy

Section:  03.02

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

Accessibility:  Keyboard Navigation

 

 

 

10) Which of the following correctly matches the molecules to the names of the functional group?

 

1.        CH3NH2               Amide

2.       CH3SCH3            Sulfide

III.    CH3CONH2       Amine

1.   IV.    CH3CO2CH3     Ester

 

1.   A) I and II

2.   B) II and IV

3.   C) III and IV

4.   D) II and III

 

Answer:  B

Difficulty: 1 Easy

Section:  03.02

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

Accessibility:  Keyboard Navigation

 

11) Consider the molecule donepezil (used to treat Alzheimer’s disease). Which of the following lists the correct functional groups present in donepezil?

 

 

 

1.   A) Amide, aromatic, ether, ketone

2.   B) Amide, aromatic, ester, ketone

3.   C) Amine, aromatic, ester, ketone

4.   D) Amine, aromatic, ether, ketone

 

Answer:  D

Difficulty: 1 Easy

Section:  03.02

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

 

 

12) Consider the molecule atenolol (a β blocker used to treat hypertension). Which of the following lists the correct functional groups present in atenolol?

 

 

 

1.   A) Primary alcohol, amide, primary amine, aromatic, ether

2.   B) Secondary alcohol, amide, secondary amine, aromatic, ether

3.   C) Secondary alcohol, amide, primary amine, aromatic, ether

4.   D) Secondary alcohol, amide, secondary amine, aromatic, ester

 

Answer:  B

Difficulty: 1 Easy

Section:  03.02

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

13) Which of the following structures contains a secondary amine?

 

 

 

1.   A) I

2.   B) II

3.   C) III

4.   D) IV

 

Answer:  C

Difficulty: 1 Easy

Section:  03.02

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

 

 

14) Which of the following structures contains a primary amine?

 

 

 

1.   A) I

2.   B) II

3.   C) III

4.   D) IV

 

Answer:  A

Difficulty: 1 Easy

Section:  03.02

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

15) Which of the following structures contains an amide?

 

 

 

1.   A) I

2.   B) II

3.   C) III

4.   D) IV

 

Answer:  D

Difficulty: 1 Easy

Section:  03.02

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

 

 

16) Which of the following structures contains an alkene?

 

 

1.   A) I

2.   B) II

3.   C) III

4.   D) IV

 

Answer:  B

Difficulty: 1 Easy

Section:  03.02

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

17) Which of the following is a tertiary amine?

 

 

1.   A) I

2.   B) II

3.   C) III

4.   D) IV

 

Answer:  B

Difficulty: 1 Easy

Section:  03.02

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

 

 

18) Which of the following is a secondary alcohol?

 

 

 

1.   A) I

2.   B) II

3.   C) III

4.   D) IV

 

Answer:  D

Difficulty: 1 Easy

Section:  03.02

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

19) Which of the following statements best describes the relationship between the surface area of a molecule and the strength of the intermolecular forces?

1.   A) The larger the surface area, the weaker the intermolecular forces.

2.   B) The larger the surface area, the stronger the intermolecular forces.

3.   C) The smaller the surface area, the stronger the intermolecular forces.

4.   D) There is no relationship between surface area and intermolecular forces.

 

Answer:  B

Difficulty: 1 Easy

Section:  03.03

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

Accessibility:  Keyboard Navigation

 

 

 

20) Rank the following compounds in order of increasing strength of intermolecular forces, putting the molecule with the weakest intermolecular force first.

 

 

1.   A) I < II < III

2.   B) II < I < III

3.   C) I < III < II

4.   D) II < III < I

 

Answer:  C

Difficulty: 2 Medium

Section:  03.03

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

21) Which of the following compounds has the lowest boiling point?

 

 

1.   A) I

2.   B) II

3.   C) III

4.   D) IV

 

Answer:  D

Difficulty: 2 Medium

Section:  03.04

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

 

 

22) Which of the following compounds has the highest boiling point?

 

 

1.   A) I

2.   B) II

3.   C) III

4.   D) IV

 

Answer:  D

Difficulty: 2 Medium

Section:  03.04

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

23) Which of the following compounds has the highest boiling point?

 

 

 

1.   A) I

2.   B) II

3.   C) III

4.   D) IV

 

Answer:  B

Difficulty: 2 Medium

Section:  03.04

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

 

 

24) Which of the following compounds has the highest boiling point?

 

 

 

1.   A) I

2.   B) II

3.   C) III

4.   D) IV

 

Answer:  D

Difficulty: 2 Medium

Section:  03.04

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

25) Which of the following compounds has the highest boiling point?

 

 

1.   A) I

2.   B) II

3.   C) III

4.   D) IV

 

Answer:  A

Difficulty: 2 Medium

Section:  03.04

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

 

 

26) Rank the following compounds in order of decreasing boiling point, putting the compound with the highest boiling point first.

 

 

1.   A) I > II > III > IV

2.   B) III > IV > II > I

3.   C) III > II > IV > I

4.   D) I > IV > II > III

 

Answer:  C

Difficulty: 1 Easy

Section:  03.04

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

27) Which of the following compounds can form intermolecular hydrogen bonds with a molecule similar to itself?

 

 

1.   A) I

2.   B) II

3.   C) III

4.   D) IV

 

Answer:  D

Difficulty: 2 Medium

Section:  03.03

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

 

 

28) What is the strongest intermolecular force present in 1-propanol?

 

 

1.   A) Ion-ion

2.   B) Hydrogen bonding

3.   C) Dipole-dipole

4.   D) Induced dipole-induced dipole

 

Answer:  B

Difficulty: 2 Medium

Section:  03.03

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

29) What intermolecular force is generally considered the strongest?

1.   A) Hydrogen bonding

2.   B) London dispersion forces

3.   C) Covalent bonds

4.   D) Dipole-dipole

 

Answer:  A

Difficulty: 1 Easy

Section:  03.03

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

Accessibility:  Keyboard Navigation

 

30) What intermolecular force is generally considered the weakest?

1.   A) Hydrogen bonding

2.   B) London dispersion forces

3.   C) Dipole-dipole

4.   D) Ion-ion

 

Answer:  B

Difficulty: 2 Medium

Section:  03.03

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

Accessibility:  Keyboard Navigation

31) Rank the following compounds in order of increasing melting point, putting the compound with the least melting point first.

 

 

 

1.   A) II < I < III

2.   B) I < III < II

3.   C) I < II < III

4.   D) III < II < I

 

Answer:  C

Difficulty: 2 Medium

Section:  03.04

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

32) Rank the following compounds in order of decreasing melting point, putting the compound with the highest melting point first.

 

 

 

1.   A) I > II > III

2.   B) II > III > I

3.   C) III > II > I

4.   D) III > I > II

 

Answer:  D

Difficulty: 2 Medium

Section:  03.04

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

 

 

33) Which of the following intermolecular forces would not form between similar molecules of the structure below?

 

 

1.   A) London dispersion forces

2.   B) Ion-ion

3.   C) Hydrogen bonding

4.   D) Dipole-dipole

 

Answer:  B

Difficulty: 2 Medium

Section:  03.03

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

34) Which of the following alkanes is expected to have the highest melting point?

 

 

1.   A) I

2.   B) II

3.   C) III

4.   D) IV

 

Answer:  D

Difficulty: 1 Easy

Section:  03.04

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

 

 

35) Which of the following compounds is expected to be the least soluble in H2O?

 

 

 

1.   A) I

2.   B) II

3.   C) III

4.   D) IV

 

Answer:  A

Difficulty: 2 Medium

Section:  03.04

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

36) Which of the following compounds is expected to be the most soluble in H2O?

 

 

1.   A) I

2.   B) II

3.   C) III

4.   D) IV

 

Answer:  B

Difficulty: 2 Medium

Section:  03.04

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

 

 

37) Which of the following compounds would be expected to be more soluble in hexane (C6H14)?

 

 

1.   A) I

2.   B) II

3.   C) III

4.   D) IV

 

Answer:  A

Difficulty: 2 Medium

Section:  03.04

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

38) Which of the following statements about the solubility of organic compounds in H2O is true?

1.   A) The non-polar part of a molecule that is not attracted to water is said to be hydrophilic.

2.   B) The non-polar part of a molecule that is not attracted to water is said to be hydrophobic.

3.   C) The polar part of a molecule that can that can bond hydrogen to water is said to be hydrophobic.

4.   D) For an organic compound with one functional group that contains an O or N atom, the compound is water soluble only if it has 35 carbons.

 

Answer:  B

Difficulty: 2 Medium

Section:  03.04

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

Accessibility:  Keyboard Navigation

 

 

 

39) Which of the following compounds is expected to be H2O soluble?

 

 

1.   A) I

2.   B) II

3.   C) III

4.   D) IV

 

Answer:  B

Difficulty: 2 Medium

Section:  03.04

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

40) What molecular features are required for soap to properly dissolve grease and oil?

1.   A) The molecule must be large.

2.   B) The molecule must contain a polar head.

3.   C) The molecule must contain a non-polar tail.

4.   D) The molecule must contain both a polar head and a non-polar tail.

 

Answer:  D

Difficulty: 2 Medium

Section:  03.06

Topic:  Functional Groups

Bloom’s:  2. Understand

Chapter:  03

Accessibility:  Keyboard Navigation

 

 

 

41) Which of the following statements about vitamin A, drawn below, is true?

 

 

 

1.   A) Vitamin A is soluble in H2

2.   B) Vitamin A is insoluble in organic solvents.

3.   C) Vitamin A contains an aromatic ring.

4.   D) Vitamin A is insoluble in H2

 

Answer:  D

Difficulty: 2 Medium

Section:  03.05

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

42) Which of the following statements about vitamin C, drawn below, is true?

 

 

1.   A) Vitamin C is insoluble in H2

2.   B) Vitamin C is soluble in H2

3.   C) Vitamin C is an aliphatic hydrocarbon.

4.   D) Vitamin C contains a ketone functional group.

 

Answer:  B

Difficulty: 2 Medium

Section:  03.05

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

 

 

43) Which of the following could most likely serve as an ionophore?

 

 

1.   A) I

2.   B) II

3.   C) III

4.   D) IV

 

Answer:  D

Difficulty: 2 Medium

Section:  03.07

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

44) The indicated carbon atom is:

 

 

1.   A) Electrophilic because it is electron-deficient.

2.   B) Nucleophilic because it is electron-deficient.

3.   C) Electrophilic because it is electron-rich.

4.   D) Nucleophilic because it is electron-rich.

 

Answer:  A

Difficulty: 1 Easy

Section:  03.08

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

 

 

45) The indicated bond is:

 

 

1.   A) Nucleophilic because it is electron-deficient.

2.   B) Electrophilic because it is electron-deficient.

3.   C) Nucleophilic because it electron-rich.

4.   D) Electrophilic because it is electron-rich.

 

Answer:  C

Difficulty: 1 Easy

Section:  03.08

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

46) The indicated bond is:

 

 

1.   A) Nucleophilic because it is electron-deficient.

2.   B) Electrophilic because it is electron-rich.

3.   C) Nucleophilic because it is electron-rich.

4.   D) Electrophilic because it is electron-deficient.

 

Answer:  D

Difficulty: 1 Easy

Section:  03.08

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

 

 

47) Which of the following lists the correct functional groups found in aspartame, the artificial sweetener?

 

 

1.   A) Amine, aromatic, carboxylic acid, ether, ketone

2.   B) Amine, amide, aromatic, carboxylic acid, ester

3.   C) Amide, alcohol, aromatic, carboxylic acid, ether

4.   D) Amine, aromatic, carboxylic acid, ester, nitrile

 

Answer:  B

Difficulty: 1 Easy

Section:  03.02

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

48) Rank the following compounds in order of decreasing boiling point, putting the compound with the highest boiling point first.

 

 

 

1.   A) I > III > IV > II

2.   B) IV > II > I > III

3.   C) IV > I > II > III

4.   D) I > IV > II > III

 

Answer:  D

Difficulty: 1 Easy

Section:  03.04

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

 

 

49) Rank the following compounds in order of increasing strength of intermolecular forces.

 

 

1.   A) I > III > IV > II

2.   B) IV > II > I > III

3.   C) IV > I > III > II

4.   D) I > IV > II > III

 

Answer:  C

Difficulty: 1 Easy

Section:  03.03

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

50) Which of the following molecules can bond hydrogen to another molecule of itself?

 

 

1.   A) I

2.   B) II

3.   C) III

4.   D) IV

 

Answer:  C

Difficulty: 1 Easy

Section:  03.03

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

 

 

51) Which C=O functional group is present in the following molecule?

 

 

1.   A) Carboxylic Acid

2.   B) Ester

3.   C) Ketone

4.   D) Aldehyde

 

Answer:  A

Difficulty: 1 Easy

Section:  03.02

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

52) Which C=O functional group is present in the following molecule?

 

 

1.   A) Carboxylic acid

2.   B) Ester

3.   C) Ketone

4.   D) Aldehyde

 

Answer:  C

Difficulty: 1 Easy

Section:  03.02

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

 

 

53) Which C=O functional group is present in the following molecule?

 

 

1.   A) Carboxylic acid

2.   B) Ester

3.   C) Ketone

4.   D) Aldehyde

 

Answer:  B

Difficulty: 1 Easy

Section:  03.02

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

54) List the intermolecular forces present in the following molecule:

 

 

1.   A) Van der Waals

2.   B) Dipole-dipole interactions

3.   C) Hydrogen bonding

4.   D) More than one of these answer choices is correct.

 

Answer:  D

Difficulty: 1 Easy

Section:  03.03

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

 

 

55) List the intermolecular forces present in the following molecule:

 

 

1.   A) Van der Waals

2.   B) Dipole-dipole interactions

3.   C) Hydrogen bonding

4.   D) More than one of these answer choices is correct.

 

Answer:  D

Difficulty: 1 Easy

Section:  03.03

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

56) List the intermolecular forces present in the following molecule:

 

 

1.   A) Van der Waals

2.   B) Dipole-dipole interactions

3.   C) Hydrogen bonding

4.   D) More than one of these answer choices is correct.

 

Answer:  A

Difficulty: 1 Easy

Section:  03.03

Topic:  Functional Groups

Bloom’s:  3. Apply

Chapter:  03

 

Organic Chemistry, 6e (Smith)

Chapter 5   Stereochemistry

 

1) What is the main carbohydrate in the seeds and roots of plants?

1.   A) Starch

2.   B) Glucose

3.   C) Cellulose

4.   D) Glycogen

 

Answer:  A

Difficulty: 1 Easy

Section:  05.01

Topic:  Stereochemistry

Chapter:  05

Accessibility:  Keyboard Navigation

 

2) Which of the following statements about starch and cellulose is true?

1.   A) Starch and cellulose are not stereoisomers.

2.   B) In cellulose, the O atom joins two rings using one equatorial and one axial bond.

3.   C) In starch, the O atom joins two rings using two equatorial bonds.

4.   D) In cellulose, the O atom joins two rings using two equatorial bonds.

 

Answer:  D

Difficulty: 1 Easy

Section:  05.01

Topic:  Stereochemistry

Chapter:  05

Accessibility:  Keyboard Navigation

 

3) Which of the following statements about constitutional isomers is not true?

1.   A) They have different IUPAC names.

2.   B) They always have the same functional groups.

3.   C) They have different physical properties.

4.   D) They have different chemical properties.

 

Answer:  B

Difficulty: 1 Easy

Section:  05.02

Topic:  Stereochemistry

Bloom’s:  2. Understand

Chapter:  05

Accessibility:  Keyboard Navigation

 

 

 

4) Which of the following statements about stereoisomers is not true?

1.   A) Stereoisomers have identical IUPAC names except for a prefix like cis or trans.

2.   B) Stereoisomers differ in configuration.

3.   C) Stereoisomers always have the same functional groups.

4.   D) Stereoisomers differ only in their structural formula.

 

Answer:  D

Difficulty: 1 Easy

Section:  05.02

Topic:  Stereochemistry

Bloom’s:  2. Understand

Chapter:  05

Accessibility:  Keyboard Navigation

 

5) What is the relationship between the following two compounds?

 

 

1.   A) Stereoisomers

2.   B) Constitutional isomers

3.   C) Identical

4.   D) Not isomers, different compounds

 

Answer:  B

Difficulty: 1 Easy

Section:  05.02

Topic:  Stereochemistry

Bloom’s:  2. Understand

Chapter:  05