Test bank for organic chemistry 2nd edition by klein

A The number of atoms B The synthesis of organic compounds required a vital force C The molecular weight D Inorganic compounds exhibited a strong nuclear force E Inorganic compounds were

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Chapter One

Topic: Introduction to Organic Chemistry Section: 1.1

Difficulty Level: Easy

1 Chemical reactions occur as a result of:

A) Attraction between opposite charges B) Nucleus–Nucleus interactions C) Motion of electrons

D) Like atoms interacting E) Combining two chemicals Ans: C

2 Credit for the first synthesis of an organic compound from an inorganic precursor is generally ascribed to:

A) Berzelius B) Arrhenius C) Kekulé D) Wöhler E) Lewis Ans: D

3 What was long thought to be the difference between inorganic and organic compounds?

A) The number of atoms B) The synthesis of organic compounds required a vital force C) The molecular weight

D) Inorganic compounds exhibited a strong nuclear force E) Inorganic compounds were composed exclusively of transition metals Ans: B

Topic: The Structural Theory of Matter Section: 1.2

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4 Constitutional isomers may not differ in what aspects?

A) Physical properties B) Atomic connectivity C) Molecular formula D) Name

E) Constitution Ans: C Topic: The Structural Theory of Matter Section: 1.2

5 What is the relationship between the following compounds?

H C C

H H C

H

C C H

H

H C

O C C C H

H H O

H

A) They are isotopes B) They are constitutional isomers C) They are the same structure D) They are composed of different elements E) There is no relationship

Ans: B Topic: The Structural Theory of Matter Section: 1.2

6 What is the relationship between the following compounds?

H

H H

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7 Carbon generally forms four bonds and is considered:

A) Tetravalent B) Divalent C) Trivalent D) Monovalent E) Qudravalent Ans: A Topic: The Structural Theory of Matter Section: 1.2

Difficulty Level: Medium

8 Which of the following compounds are constitutional isomers of each other?

C C C C C C Br

C H H

H H H

Br CH

H H H

H

C C C C C C C C

H Cl Br

H H

H

H H

C C C C C C Br C

H Cl Br

C

H

H H H

H H

A) I & II B) III & IV C) I, II & III D) II, III & IV E) All of these Ans: E

C C Cl Cl

H H

H

Cl

C C Cl Cl

H Cl

H

Cl

C C Cl Cl

H H

H

C C Cl H

H H

Cl

A) I & II B) III & IV C) II & III D) I & IV E) All of these Ans: D Topic: The Structural Theory of Matter Section: 1.2

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C N C H

H

O H

H C H

H

C C O N C H H

H

H H

H

H C H H

H C O N H C H

H H C

C N C

C

O H H

H H

H

H H

A) I & II B) III & IV C) I, II & III D) I & IV E) All of these Ans: C Topic: The Structural Theory of Matter Section: 1.2

11 Draw three constitutional isomers that have molecular formula C4H8BrCl Ans:

H

H H

H

H Cl

Br H

H H

There are additional correct answers

Difficulty Level: Hard

12 Draw three constitutional isomers that have molecular formula C4H8O

Ans:

H H

H

C H H H

There are additional correct answers

Topic: Electrons, bonds, and Lewis structures Section: 1.3

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13 What force is not taken into account in the formation of a covalent bond?

A) Repulsion between two positively charged nuclei B) Repulsion between electron clouds on individual atoms C) Force of attraction between positively charged nuclei and electrons D) Repulsion of electrons by neutrons

E) All forces listed are involved in forming a covalent bond Ans: D

14 What is the correct Lewis dot structure for S?

II

SIII

A) I B) II C) III D) IV E) V Ans: C Topic: Electrons, bonds, and Lewis structures Section: 1.3

15 What is the correct Lewis dot structure for C?

II

CIII

A) I B) II C) III D) IV E) V Ans: E

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16 What is the correct Lewis structure for PH3?

H

H H

A) I B) II C) III D) IV E) V Ans: A

17 What is the correct Lewis structure for COCl2?

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18 What is the correct Lewis structure for CH3CO2H?

H C

C H

19 Which of the following compounds has two lone pairs on the central atom?

20 What is the formal charge on oxygen in the following structure?

H O H

H H

A) B) 1-C) 2+

2-D) 1+

E) 0Ans: D Topic: Identifying Formal Charges

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Section: 1.4 Difficulty Level: Easy

21 What is the formal charge on nitrogen in the following structure?

2-D) 1+

E) 0Ans: D

Topic: Identifying Formal Charges Section: 1.4

C C C

O H

H

A) 0 B) 1+

C) 2+

D) E) 2-Ans: B

1-Topic: Identifying Formal Charges Section: 1.4

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C O C

D) E) 0Ans: E Topic: Identifying Formal Charges Section: 1.4

1-Difficulty Level: Easy

24 Which of the following structures have zero formal charge on carbon atom?

25 Which of the following structures have 1- formal charge on sulfur atom?

H S H

C H

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26 Which of the following structures have 1+ formal charge on sulfur atom?

H S H

C H

27 What are the formal charges on boron and fluorine in the following structure?

H N H

H F B

F F

A) B = 1+, N = 1+

B) B = 1+, N = C) B = 1-, N = 1-D) B = 1-, N = 1+

1-E) B = 1-, N = 0Ans: D Topic: Identifying Formal Charges Section: 1.4

28 What are the formal charges on boron and oxygen in the following structure?

C O C F B

F F

H H H

H

H H

A) B = , O = B) B = 1-, O = 1+

1-C) B = 1+, O = 1+

D) B = 1+, O = 1- E) B = 1-, O = 0Ans: B Topic: Identifying Formal Charges

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Section: 1.4 Difficulty Level: Medium

29 Which of the following structures have 1+ formal charge on the central atom?

HH

H : Be : H H : B : H . H : N : H . H : N : H . H : O : H .

A) IB) IIC) IIID) III & V E) IV & VAns: E

30 Which of the following structures have formal charge on at least one atom?

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31 Which of the following structures have 1- formal charge on nitrogen atom?

H H

32 The bonding pattern of oxygen with a formal charge of –1 could be described as:

A) One lone pair of electrons and three single bondsB) Two lone pairs of electrons and two single bondsC) Three lone pairs of electrons, and one single bondD) One lone pair of electrons, one single, and one double bond E) Zero lone pairs, and two single and one double bond

Ans: C Topic: Identifying Formal Charges Section: 1.4, 1.3

33 In ammonium ion, nitrogen has a valence of 4, and zero nonbonding electrons What is the correct formal charge of nitrogen with 4 covalent bonds?

A) B) 2+

2-C) D) 1+

1-E) 0Ans: D Topic: Identifying Formal Charges Section: 1.4, 1.3

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34 What is the correct Lewis structure for nitric acid (HNO3) including the formal charges?

O N O

O H

N OO O

O O

O H

O N O O H

A) IB) IIC) IIID) IV E) None of theseAns: D Topic: Identifying Formal Charges Section: 1.4, 1.3

35 What is the correct Lewis structure for hydrocyanic acid (HCN) including the formal charges, if any?

36 What is the correct Lewis structure for SCN— including the formal charges, if any?

A) IB) IIC) IIID) IV E) VAns: A Topic: Identifying Formal Charges

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Section: 1.4, 1.3 Difficulty Level: Hard

37 What is the correct Lewis structure for N2O including the formal charges, if any?

A) IB) IIC) IIID) IV E) VAns: B

Topic: Identifying Formal Charges Section: 1.4, 1.3

38 What is the correct Lewis structure for hydrazoic acid (HN3) including the formal charges, if any?

A) IB) IIC) IIID) IV E) VAns: A

39 Draw Lewis structure for NH2CN including formal charges, if any?

Ans:

N H

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40 Draw Lewis structure for –CH2CN including formal charges?

Ans:

C H

H

41 Draw Lewis structure for ozone (O3,) including formal charges, if any?

Ans:

Topic: Induction and Polar Covalent bond Section: 1.5

42 The electronegativity of elements on the periodic table tends to increase _

A) From left to right, top to bottom B) From right to left, bottom to topC) From left to right, bottom to top D) From right to left, top to bottom E) F

Ans: C

43 Which of the following is the least electronegative element?

A) B B) CC) ND) O E) FAns: A Topic: Induction and Polar Covalent bond Section: 1.5

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44 Which of the following is the most electronegative element?

A) B B) CC) ND) O E) HAns: D Topic: Induction and Polar Covalent bond Section: 1.5

45 Which of the following is the least electronegative element?

A) P B) NC) MgD) Si E) KAns: E

46 Which of the following is the most electronegative element?

A) P B) NC) SD) O E) FAns: E

47 What is the correct order of increasing electronegativity for Rb, F and O?

A) Rb < F < O B) Rb < O < F C) O < F < Rb D) F < Rb < O E) None of theseAns: B

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48 Which of the following series has the correct order of elements in increasing electronegativity?

A) C < N < B < Br B) P < N < As < F C) Li < B < N < F D) Cl < Cs < C < Co E) Be < B < Ba < Br Ans: C

49 The Cl—Cl bond is best described as _

A) Nonpolar covalent B) Polar covalent C) Ionic

D) Coordinate covalent E) None of these Ans: A Topic: Induction and Polar Covalent bond Section: 1.5

50 The C—Cl bond is best described as _

D) Coordinate covalent E) None of these Ans: B Topic: Induction and Polar Covalent bond Section: 1.5

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51 The bond between potassium and oxygen is best described as _

D) Coordinate covalent E) None of these Ans: C Topic: Induction and Polar Covalent bond Section: 1.5

52 The bond between carbon and hydrogen is best described as _

D) Coordinate covalent E) None of these Ans: A

53 Which of the following is the correct depiction of induction for a C—F bond?

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54 Which of the following is the correct representation of dipole for P—Cl bond?

55 Which of the following is the correct representation of partial charges at the indicated atoms?

II

III

Cl C C C H O

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56 Which atom has the most δ+ in the following compound?

57 Which of the following statements best describes the C—Cl bond in the following compound?

Cl C C C H

H H

A) nonpolar; no dipole B) polar; δ+ at carbon and δ– at chlorine C) polar; δ– at carbon and δ+ at chlorine D) ionic

E) None of these Ans: B Topic: Induction and Polar Covalent bond Section: 1.5

58 Which of the following compounds have both polar covalent and ionic bonds?

A) NH4Br B) H2O2

C) HCND) H2S E) None of these Ans: A

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59 For the following compound identify the polar covalent bonds and indicate the direction

of dipole moment using δ+ and δ-

Cl C C C H O

Ans:

Cl C C C H O

60 For the following compound identify the polar covalent bonds and indicate the direction

of dipole moment using δ+ and δ-

Cl C C N H O

61 For NaSCH3, identify each bond as polar covalent, nonpolar covalent or ionic

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62 For the following compound, identify each bond as polar covalent, nonpolar covalent or ionic and place a δ+ on the most electropositive carbon

H

C C F O

Ans:

H

C C F O

63 Orbitals with the same energy are called _

A) Quantum orbitals B) Atomic orbitals C) Antibonding orbitals D) Bonding orbitals E) Degenerate orbitals Ans: E

Topic: Atomic Orbitals Section: 1.6

64 What is the letter designation for the following atomic orbital?

A) s B) p C) d D) f E) g Ans: B Topic: Atomic Orbitals

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65 What is the letter designation for the following atomic orbital?

A) s B) p C) d D) f E) g Ans: C

66 In quantum mechanics a node (nodal surface or plane) is:

A) location where ψ is negative B) location where ψ is positive C) location where ψ2 is positive D) location where ψ2 is negative

E) location where ψ is zero Ans: E

67 Which of the following principle states that “Each orbital can accommodate a maximum

of two electrons with opposite spin”?

A) Aufbau principle B) Pauli exclusion principle C) Hund’s Rule

D) Heizenberg Uncertainty principle E) Le Chatelier principle

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68 Which of the following principle states “When orbitals of equal energy are available, every orbital gets one electron before any gets two electrons”?

A) Aufbau principle B) Pauli exclusion principle C) Hund’s Rule

D) Heizenberg Uncertainty principle E) Le Chatelier principle

Ans: C

69 Which of the following represents ground state electron configuration for phosphorous?

A) 1s2 2s2 2p6 3s1 3p4B) 1s2 2s2 2p6 3s2 3p4C) 1s2 2s2 2p6 3s2 3p3D) 1s2 2s2 2p6 3s2 3p2

E) 1s2 2s2 2p6 3s2 3p5

Ans: C Topic: Atomic Orbitals Section: 1.6

70 The atomic number for nitrogen is 7 Which of the following represents ground state electron configuration for nitrogen?

A) 1s2 2s1 2p4B) 1s2 2p5C) 2s2 2p5D) 1s2 2s2 2p3

E) 1s2 2s2 3s3

Ans: D Topic: Atomic Orbitals Section: 1.6

71 Which element has the electron configuration 1s2 2s2 2p6 3s2 3p5? A) oxygen

B) fluorine C) sulfur D) chlorine E) bromine Ans: D

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72 Which element has the electron configuration 1s2 2s2 2p6 3s2 3p3? A) Cl

B) S C) P D) Al E) N Ans: C Topic: Atomic Orbitals Section: 1.6

73 What is the electronic configuration for the nitride ion?

A) 1s2 2s2 2p0

B) 1s2 2s2 2p2C) 1s2 2s22p3D) 1s2 2s22p4E) 1s2 2s2 2p6

Ans: E Topic: Atomic Orbitals Section: 1.6

74 What is the electronic configuration for the magnesium ion?

A) 1s2 2s2 2p63s2 B) 1s2 2s2 2p6

C) 1s2 2s22p4D) 1s2 2s22p63s1 E) 1s2 2s2 2p63s22p2

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75 What is the electronic configuration for the oxide ion?

A) 1s2 2s2 2p6 B) 1s2 2s2 2p2C) 1s2 2s22p4D) 1s2 2s02p6 E) 1s2 2s2 2p63s22p2

Ans: A Topic: Atomic Orbitals Section: 1.6

76 Which element has the following electronic configuration?

A) boronB) carbon C) silicon D) nitrogenE) fluorineAns: D

77 Which element has the following electronic configuration?

A) boronB) carbon C) silicon D) nitrogenE) fluorineAns: E Topic: Atomic Orbitals Section: 1.6

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78 The following ground state electron configuration violates _

A) the Aufbau principleB) the Pauli Exclusion principle C) Hund’s Rule

D) Heisenberg’s Uncertainty principleE) None of these

Ans: C Topic: Atomic Orbitals Section: 1.6

79 The following ground state electron configuration violates

Ans: A Topic: Atomic Orbitals Section: 1.6

80 The following ground state electron configuration violates

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81 Ar, K+, and Cl– have equal numbers of electrons, and are considered isoelectronic

Provide the ground state electron configuration for them

Ans: 1s2 2s2 2p6 3s2 3p6

Topic: Valence Bond Theory Section: 1.7

82 Constructive interference of waves results in _

A) a wave with smaller amplitudeB) a wave with larger amplitude C) cancellation of both waves D) formation of a node

E) Both C & DAns: B

Topic: Valence Bond Theory Section: 1.7

83 Destructive interference of waves results in _

A) a wave with smaller amplitudeB) a wave with larger amplitude C) cancellation of both waves D) formation of a node

E) Both C& DAns: E Topic: Valence Bond Theory Section: 1.7

84 All single bonds can be classified as:

A) nonpolar covalentB) polar covalent C) ionic

D) σ bondsE) π bondsAns: D Topic: Valence Bond Theory Section: 1.7

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85 Which of the bonding type has circular symmetry with respect to the bond axis?

A) σ bondB) π bond C) δ bond D) covalent bondE) ionic bondAns: A Topic: Molecular orbital Theory Section: 1.8

86 The difference between valence bond theory and molecular orbital (MO) theory is:

A) valence bond theory requires the linear combination of atomic orbitalsB) MO theory requires the linear combination of atomic orbitals

C) valence bond theory considers only individual atomic orbitals D) Both A & B

E) Both B & CAns: E

Topic: Molecular orbital Theory Section: 1.8

87 How many molecular orbitals are formed, when the 1s orbitals of two hydrogen atoms

combine to form a hydrogen molecule?

A) 1B) 2 C) 3 D) 4E) 5 Ans: B

88 Which molecular orbitals are formed, when the 1s orbitals of two hydrogen atoms

combine to form a hydrogen molecule?

A) Two bonding molecular orbitalsB) Only one bonding molecular orbital C) One bonding and one antibonding molecular orbital D) Two antibonding molecular orbitals

E) Only one antibonding orbital Ans: C

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89 How are electrons distributed in the molecular orbitals, when the 1s orbitals of two

hydrogen atoms combine to form a hydrogen molecule?

A) 2 electrons in the bonding molecular orbitalB) 1 electron in the bonding molecular orbital, 1 electron in the non–bonding molecular orbital

C) 1 electron in the bonding molecular orbital, 1 electron in the antibonding molecular orbital

D) 2 electrons in the antibonding molecular orbitalE) 2 electrons in the non–bonding molecular orbital Ans: A

90 According to molecular orbital theory the highest energy molecular orbital that is occupied with an electron is referred to as:

A) degenerateB) antibonding C) the LCAO D) the LUMOE) the HOMOAns: E Topic: Molecular orbital Theory Section: 1.8

91 According to molecular orbital theory the lowest energy molecular orbital that is unoccupied with an electron is referred to as:

A) degenerateB) antibonding C) the LCAO D) the LUMOE) the HOMOAns: D Topic: Molecular orbital Theory Section: 1.8

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92 Which of the following statement is incorrect, when the 1s atomic orbitals of two

hydrogen atoms results in constructive interference?

A) A sigma bonding molecular orbital is formed

B) The bonding molecular orbital formed is lower in energy than the 1s atomic orbital

C) The bonding molecular orbital formed has a node between the atoms D) The bonding molecular orbital formed has circular symmetry

E) A maximum of two electrons may occupy the bonding molecular orbitalAns: C

93 Which of the following molecules could not exist, according to the molecular orbital theory?

94 According to molecular orbital theory, the constructive interference of two atomic orbitals results in _

Ans: bonding molecular orbital Topic: Molecular orbital Theory

95 According to molecular orbital theory, the destructive interference of two atomic orbitals results in _

Ans: antibonding molecular orbital Topic: Molecular orbital Theory

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96 Interaction of the following two atomic orbitals results in what kind of molecular orbital, in the orientation shown?

+

Ans: σ bonding molecular orbital Topic: Molecular orbital Theory

Ans: π bonding molecular orbital Topic: Molecular orbital Theory

Ans: π∗ antibonding molecular orbital Topic: Hybridized Atomic orbitals

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99 What is the hybridization state of the oxygen atom in the following compound?

E) s 2 p

Ans: C

Topic: Hybridized Atomic orbitals Section: 1.9

100 What is the hybridization state of the nitrogen atom in the following compound?

E) s 2 p

Ans: C Topic: Hybridized Atomic orbitals Section: 1.9

101 What is the hybridization state of the boron atom in the following compound?

B

F

A) sp B) sp 2 C) sp 3 D) sp 3 d

E) s 2 p

Ans: B Topic: Hybridized Atomic orbitals Section: 1.9

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