Chapter 1

Chapter 1

MULTIPLE CHOICE QUESTIONS Solomons Chapter 1

(Answers on page 14) Topic: Atomic Orbitals, Molecular Orbitals Hybridization

Topic: Lewis Structures, Formal Charges 5. Listed below are electron dot formulas for several simple molecules and ions. All valence electrons are shown; however, electrical charges have been omitted deliberately.
H .. H:B:H .. H II H .. H:N:H .. III H .. H:N:H .. H IV H .. H:O:H .. V

H : Be : H

1. When the 1s orbitals of two hydrogen atoms combine to form a hydrogen molecule, how many molecular orbitals are formed? A) 1 B) 2 C) 3 D) 4 E) 5 2. When the ls orbitals of two hydrogen atoms combine to form a hydrogen molecule, which molecular orbitals are formed? A) One bonding molecular orbital only B) Two bonding molecular orbitals C) One bonding molecular orbital and one antibonding molecular orbital D) Two antibonding molecular orbitals E) Three bonding molecular orbitals 3. The following electron configuration represents _______.
1s 2sp3 2sp3 2sp3 2sp3 the ground state of boron. the sp3 hybridized state of carbon. the sp3 hybridized state of nitrogen. the ground state of carbon. an excited state of carbon.

A) B) C) D) E)

Which of the structures actually bear(s) a positive charge? I II III III & V IV & V

6. What is the formal charge on oxygen in the following structure? ..

H3C O CH3 CH3

A) B) C) D) E)

+2 +1 0 -1 -2

A) B) C) D) E) 4. A) B) C) D) E)

7. In which structure(s) below does the oxygen have a formal charge of +1?
H

..
O H

.. O: .. II

C H

..
O

H3C

..
CH3

CH3

Identify the atomic orbitals in the C-C sigma bond in ethyne. (2sp2, 2sp2) (2sp3, 2sp3) (2sp, 2sp) (2p, 2p) (2sp, 1s)

A) B) C) D) E)

I I only II only I and III I and IV I, III, and IV

s

III

IV

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8. Which structure(s) contain(s) an oxygen that bears a formal charge of +1? .. .. :O :O .. .. .. .. : O C O: H C H3C O H H3C O CH3 C : O. : : O. : : O. : . . . H CH3 I II III IV V A) B) C) D) E) I and II III and IV V II I and V

Topic: Lewis Structures, Formal Charges 11. Which of the following is an ion with a single negative charge? .. A) H3C O : .. .. .... B) : O N O : .. .. C) : O: .. :O N : O. : . D) All of these E) None of these

9. Which of the following molecules or ions has a nitrogen with a formal charge of -1? (Charges on ions have been omitted.) .. A) : N H
H

12. Which is NOT a correct Lewis structure? .. A) H N F : .. B)

H
H H

B) H C) H D) H3C E) H3C

..
N H

C H .. O ..

.. F: ..
.. O H . .. . :O H
B

..
N H

C) H
CH3

D)
H

..
N H C

CH3
N:

: O. H . E) None of these

.. O ..

10. In which structure(s) below does nitrogen have a formal charge of +1?
H3C N H CH2 H3C

13. Listed below are electron dot formulas for several simple molecules and ions. All valence electrons are shown; however, electrical charges have been omitted deliberately.
H3C

.. N ..

..
N

.. OH ..

H3C

..

NH2

..
N CH3

CH3

H : Be : H

II

III

IV

H .. H:B:H .. H II

H .. H:N:H .. III

H .. H:N:H .. H IV

H .. H:O:H .. V

A) B) C) D) E)

I II and IV III and V I and V V

A) B) C) D) E)

Which of the structures is negatively charged? I II III IV V

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Topic: Lewis Structures, Formal Charges 14. Which compound contains a nitrogen atom with a formal positive charge?
H N N N

Topic: Lewis Structures, Formal Charges Molecular Geometry 17. Expansion of the valence shell to accommodate more than eight electrons is possible with: A) Fluorine B) Nitrogen C) Carbon D) Sulfur E) Beryllium 18. A) B) C) D) E) 19. A) B) C) D) E) 20. A) B) C) D) E) 21. A) B) C) D) E) 22. A) B) C) D) E) Based on VSEPR theory, which of the following would have a trigonal planar shape? CH3)3N HCN NH4+ CH3! CH3+ What shape does the methyl cation, CH3+, have? Octahedral Tetrahedral Trigonal planar Linear Trigonal pyramidal What bond angle is associated with a tetrahedral molecule? 120 109.5 180 90 45 What would be the spatial arrangement of the atoms of the methyl anion, :CH3-? Octahedral Tetrahedral Trigonal planar Linear Trigonal pyramidal Which of these structures would be a perfectly regular tetrahedron? CH3Br CH2Br2 CHBr3 CBr4 More than one of these

II

III

A) B) C) D) E)

I II III More than one of the above None of the above

15. In which of these cases does the central atom have a zero formal charge? A) HFH H B) C)
H3C O F
F B F F

CH3

D)
H3C

H N CH3

E)
H3C

H CH3

CH3

CH3

16. The formal charge on sulfur in sulfuric acid is:

O H O S O O H

A) B) C) D) E)

0 -1 +1 -2 +2

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Topic: Periodic Properties, Electronegativity 23. A) B) C) D) E) Select the most electronegative element. H O N B C

Topic: Atomic Orbitals, Bonding 28. A) B) C) D) E) Which of these substances contains both covalent and ionic bonds? NH4Cl H2O2 CH4 HCN H2S

Topic: Atomic Orbitals, Hybridization 24. A) B) C) D) E) 25. A) B) C) D) E) 26. A) B) C) D) E) In which molecule is the central atom sp hybridized? CH4 NH3 H2O All of these None of these Which compound has the shortest carbon-carbon bond(s)? CH3CH3 CH2=CH2 HC"CH CH3CH2CH3 All carbon-carbon bonds are the same length. Which of the following contains an sp2-hybridized carbon? CH4 CH3:! CH3CH3 CH3+ HC"CH
3

Topic: Atomic Orbitals, Periodic Trends, Electronegativity 29. A) B) C) D) E) The greatest degree of ionic character is anticipated for the bond between: H and C H and Cl C and Cl H and Br Br and Cl

Topic: Atomic Orbitals, Hybridization 30. A) B) C) D) Which molecule contains an sp-hybridized carbon? HCN CH2=CH2 CH3Cl
H C O H

E) CH3CH3 Topic: Atomic Orbitals, Lewis structures, Resonance 31. Which of the structures below is not expected to contribute to the CO2 resonance hybrid? A)
O C O

27. Which is the shortest of the carbon-carbon single bonds indicated by arrows in the following compounds? A)
H3C CH3

B)
H3C C

B) O C) O D) E)

C C C
C

O O O
O

C)
H3C

CH CH2

CH
C C CH

D)
HC

E) H2C
HC C CH

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Topic: Atomic Orbitals, Lewis Structures, Resonance 32. Which of the following pairs are NOT resonance structures? A) and H 3C O N O : H 3C O N O :
: : : : : : : :
:
Br
O C O

and

C)
: : :
H 3C O N O

O O

and

H 3C

D) Each of these pairs represents resonance structures. E) None of these pairs represents resonance structures. Topic: Empirical and Molecular Formulas 33. A) B) C) D) E) What is the empirical formula for cyclohexane? (Its molecular formula is C6H12.) CH CH2 C2H4 C6H6 C2H2

34. A compound consists only of carbon, hydrogen and oxygen. Elemental analysis gave: C, 70.5%, H, 13.8%. The molecular weight of the compound was found to be 103 +/- 3. What is the molecular formula for the compound? A) C6H12O B) C5H12O2 C) C3H2O4 D) C3H6O3 E) C6H14O Topic: Isomerism 35. Which of the following is a set of constitutional isomers?
Br Br Br

II

III

A) B) C) D) E)

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

.. ..

B)

Topic: General 36. Credit for the first synthesis of an organic compound from an inorganic precursor is usually given to: A) Berzelius B) Arrhenius C) Kekule D) Wohler E) Lewis Topic: Isomerism 37. CH3CH2OCH2CH3 and CH3CH2CH2CH2OH are examples of what are now termed: A) Structural isomers B) Resonance structures C) Functional isomers D) Empirical isomers E) Constitutional isomers Topic: Hybridization 38. What is the approximate hybridization state of the oxygen molecule in ethanol, C2H5OH? A) sp B) sp2 C) sp3 D) p3 E) d2sp3 Topic: Lewis structures, Hybridization 39. Which molecule has a non-linear structure (i.e., for which molecule are the nuclei not in a straight line)? A) O=C=O B) HOH C) HCl D) HC"N E) HC"CH Topic: Isomerism 40. Which of the following structures represent compounds that are constitutional isomers of each other?

: ..

: ..

: ..

. .. .

.. : ..

IV

A) B) C) D) E)

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

II

III

IV

10

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Topic: Isomerism 41. Which compound is not an isomer of the others?

O OH O OH

Topic: Isomerism 44. Which of the following represent a pair of constitutional isomers? A) and B) CH3CH=CH2 and CH2=CHCH3 Br Br C)
H Br H Br

A) B) C) D) E)

I II III I II III IV All of the above are isomers of each other.

IV

and Br
H Br

D)
Br

H H

and

H Br

42. Consider the following: CH3CH2CH=CHCH2CH3 I CH3CH=CHCH2CH2CH3 III A) B) C) D) E) CH3CH2CH2CH2CH=CH2 II CH2=CHCH2CH2CH2CH3 IV

E) More than one of these 45. A) B) C) D) E) Cis-trans: isomerism is possible only in the case of: CH2=CBr2 CH2=CHBr BrCH=CHBr Br2C=CHBr Br2C=CBr2

Which two structures represent the same compound? I and II II and III I and III II and IV None of these

Topic: Atomic Orbitals, Hybridization, Bonding 46. Identify the atomic orbitals involved in the C-2---C-3 sigma bond (indicated by an arrow) in the following molecule:
1 4 6 2 3

43. Consider the following: CH3CH2CH2CH=CHCH2CH2CH3 I CH3CH2CH2CH2CH2CH2CH=CH2 II A) B) C) D) E) sp2, sp2 sp2, sp sp2, sp3 sp3, sp2 sp, sp2
7 5

A) B) C) D) E)

CH3CH2CH=CHCH2CH2CH2CH3 CH2=CHCH2CH2CH2CH2CH2CH3 III IV Which structures can exist as cis-trAns: isomers? I and II I and III I and IV II and III I alone

Topic: Molecular Geometry 47. Based on the VSEPR theory, which of the following would have a tetrahedral arrangement of electrons around the central atom? A) BH3 B) NO2 ! C) SiH4 D) CO3 2! E) SO3

11

12

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Topic: Periodic Trends, Electronegativity 48. A) B) C) D) E) Select the least electronegative element P N Mg Si K Solomons Chapter 1
Frga 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 Svar B C C C E B E B A A D A B D E A D E C B E D B D C D D A B A D C B E E D E C B C A D B E C E C E D E Rtt/Fel 2009 Kpmmentar

Topic: Atomic Orbitals, Hybridization 49. In which molecule(s) can the molecular geometry be attributed to an sp2 hybridized central atom? A) PBr3 B) CH4 C) CHCl3 D) HNO2 E) None of the above has an sp2 hybridized central atom Topic: Bonding, Atomic Orbitals, Hybridization 50. Which molecule has the shortest carbon-carbon single bond?

II

III

A) B) C) D) E)

I II III IV V

IV

13

14