Bruice Organic Chemistry 6e

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Organic Chemistry, 6e (Bruice)
Chapter 1 Electronic Structure and Bonding Acids and Bases
1) Atoms with the same number of protons but different numbers of neutrons are called
________.
Answer: isotopes
Section: 1-1
2) Which of the following elements does this electronic configuration represent?
1s2 2s2 2p5
A) F
B) C
C) N
D) Al
E) O
Answer: A
Section: 1-2
3) How many unpaired electrons are present in the isolated carbon atom (atomic number = 6)?
A) none
B) one
C) two
D) three
E) four
Answer: C
Section: 1-2
4) Which of the following is the electronic configuration of the element Fe?
A) 1s2 2s2 2p6 3s2 3p6 4s2 3d6
B) 1s2 2s2 2p6 3s2 3p8 3d6
C) 1s2 2s2 2p8 3s2 3p6 4s2 3d6
D) 1s2 2s2 2p6 3s2 3p6 4s2 4d6
E) 1s2 2s2 2p6 3s2 3p6 4s2 4p6
Answer: A
Section: 1-2
5) The atomic number of boron is 5. The correct electronic configuration of boron is:
A) 1s22s3
B) 1s22p3
C) 1s22s22p1
D) 2s22p3
E) 1s22s23s1
Answer: C
Section: 1-2
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6) Which of the following statements correctly describes the third electron shell that surrounds
the nucleus of an atom?
A) The third shell contains only s and p atomic orbitals.
B) The maximum number of electrons that can occupy the third shell is 18.
C) The total number of atomic orbitals present in the third shell is 16.
D) The third shell can contain f orbitals.
E) All third shell elements must have d electrons.
Answer: B
Section: 1-2
7) Ar, K+, Cl- are isoelectronic elements (elements with the same number of electrons). What
orbital does the last electron occupy?
Answer: 3p orbital
Section: 1-2
8) The compound methylamine, CH3NH2, contains a C-N bond. In this bond, which of the
following best describes the charge on the nitrogen atom?
A) +1
B) slightly positive
C) uncharged
D) slightly negative
E) -1
Answer: D
Section: 1-3
9) Which of the compounds below have bonds that are predominantly ionic?
A) KCl
B) CF4
C) NH3
D) both A and B
E) both B and C
Answer: A
Section: 1-3
10) What type of bonding is most important in CH3CH2CH2CH2CH2CH3?
A) ionic
B) hydrogen
C) covalent
D) polar
Answer: C
Section: 1-3

11) Which of the following contain(s) polar covalent bonds?
A) NH3
B) Na2O
C) H2
D) KF
E) both A and C
Answer: A
Section: 1-3
12) Which of the following covalent bonds has the largest dipole moment?
A) C-C
B) C-H
C) C-O
D) H-N
E) H-F
Answer: E
Section: 1-3
13) Using the symbol +and -, indicate the direction of the polarity in the indicated bond.
Answer:
Section: 1-3
14) Covalent bonds may be polar or nonpolar. What property of the atoms forming a given bond
determines this?
Answer: electronegativity
Section: 1-3
15) Provide the mathematical equation for the dipole moment of a bond, and identify the
variables.
Answer: = e d, where is the bond dipole moment, e is the amount of charge which is
separated, and d is the distance over which the charge is separated.
Section: 1-3

16) The formal charge on nitrogen in the compound below is ________.
A) +2
B) +1
C) 0
D) -1
E) -2
Answer: B
Section: 1-4
17) Which of the following is the most likely electronic structure for C2H2?
A)
B)
C)
D)
HCCH
E)
Answer: D
Section: 1-4

18) Which of the following structures, including formal charges, is correct for diazomethane,
CH2N2?
A)
:CH2NN:
B)
C)
D)
E)
Answer: D
Section: 1-4
19) What are the formal charges on nitrogen and the starred oxygen atom in the following
molecule?
A) N = -1, O = 0
B) N = +1, O = -1
C) N = +1, O = +1
D) N = -1, O = -1
E) N= +1, O = 0
Answer: E
Section: 1-4

20) Draw the Kekul structure for each of the following:
a. CH3CH2OH b. CH3CHO
c. (CH3)3C+
Answer:
Section: 1-4
21) The Kekul structure of pentane is shown below. Draw the condensed structural formula
which corresponds to this Lewis structure.
Answer: CH3(CH2)3CH3
Section: 1-4
22) Draw condensed structures for the four compounds with formula C3H9N.
Answer:
CH3CH2CH2NH2
CH3CH2NHCH3
(CH3)2CHNH2
(CH3)3N
Section: 1-4
23) Write a Lewis structure for the molecule given and show all formal charges.
CH2CO
Answer:
Section: 1-4

24) Expand the condensed structure below to show the covalent bonds and the lone-pair
electrons.
(CH3)2CHCH2CHO
Answer:
Section: 1-4
25) Draw the Lewis structure for CH3N2+.
Answer:
Section: 1-4
26) How many distinct and degenerate p orbitals exist in the second electron shell, where n = 2?
A) 0
B) 1
C) 2
D) 3
E) 4
Answer: D
Section: 1-5
27) Draw the shape of a 2p orbital.
Answer:
Section: 1-5
28) Consider the interaction of two hydrogen 1s atomic orbitals of the same phase. Which of the
statements below is an incorrect description of this interaction?
A) A sigma bonding molecular orbital is formed.
B) The molecular orbital formed is lower in energy than a hydrogen 1s atomic orbital.
C) The molecular orbital formed has a node between the atoms.
D) The molecular orbital formed is cylindrically symmetric.
E) A maximum of two electrons may occupy the molecular orbital formed.
Answer: C
Section: 1-6
29) Both sigma () and pi () bonds can be formed by overlapping p orbitals. Describe the

difference.
Answer: Sigma bonds are formed from the overlap of atomic orbitals along a circular axis of
symmetrical nature, i.e., head-on overlap. All single bonds are sigma bonds.
Pi bonds are formed from the overlap of atomic orbitals along a non-symmetrical (parallel) axis,
i.e., side-to-side overlap. Double and triple bonds contain both sigma and pi bonds.
Section: 1-6
30) What kind of molecular orbital (, *, , or *) results when the two atomic orbitals shown
below interact in the manner indicated?
Answer: *
Section: 1-6
Answer:
Section: 1-6
Answer:
Section: 1-6
Answer: *
Section: 1-6

Answer: *
Section: 1-6
35) Choose the correct hybridization for the atom indicated in the molecule below.
CH3CH2CH2CH3
A) sp
B) sp2
C) sp3
D) none of the above
Answer: C
Section: 1-7
36) What orbitals are used to form the covalent bonds in butane (CH3CH2CH2CH3)?
Answer: The carbon-carbon bonds are formed by the overlap of two carbon sp3 hybrid atomic
orbitals. The carbon-hydrogen bonds are formed by the overlap of a carbon sp3 hybrid atomic
orbital and a hydrogen s orbital.
Section: 1-7
37) Which carbon(s) in the following molecule is (are) sp hybridized?
A) carbon 1
B) carbon 2
C) carbons 1, 3
D) carbons 4
E) carbons 4, 5
Answer: E
Section: 1-9

38) Which of the following is an sp2 hybridized carbon?
A)
B)
CH3
C)
D) A and B
E) A, B and C
Answer: A
Section: 1-10
39) What is the predicted shape, bond angle, and hybridization for +CH3?
A) trigonal planar, 120, sp2
B) trigonal planar, 120, sp3
C) trigonal planar, 109.5, sp2
D) trigonal pyramidal, 120, sp2
E) trigonal pyramidal, 109.5, sp2
Answer: A
Section: 1-10
40) What orbitals overlap to create the H-C bond in CH3+?
A) sp3-sp3
B) sp2-sp3
C) s-p
D) s-sp2
E) s-sp3
Answer: D
Section: 1-10
41) The lone-pair electrons of the methyl anion occupy a(n) ________ orbital.
A) s
B) p
C) sp
D) sp2
E) sp3
Answer: E
Section: 1-10

42) Which of the following is closest to the C-O-C bond angle in CH3-O-CH3?
A) 180
B) 120
C) 109.5
D) 90
E) 160
Answer: C
Section: 1-11
43) Each lone pair of electrons on the O atom in methanol (CH3OH) occupies a(n) ________
orbital.
A) s
B) p
C) sp
D) sp2
E) sp3
Answer: E
Section: 1-11
44) The N-H single bond in methyl amine (CH3NH2) is a ________ bond formed by the overlap
of a(n) ________ orbital on N and a(n) ________ orbital on H.
A) ; sp2; s
B) ; sp3 ; s
C) ; sp3 ; s
D) ; sp2 ; p
E) ; p ; p
Answer: B
Section: 1-12
45) Triethylamine [(CH3CH2)3N] is a molecule in which the nitrogen atom is ________
hybridized and the CNC bond angle is ________.
A) sp2, >109.5
B) sp2, <109.5
C) sp3, >109.5
D) sp3, <109.5
E) sp, 109.5
Answer: D
Section: 1-12

46) The N-H bond in the ammonium ion, NH4+, is formed by the overlap of what two orbitals?
A) sp3-sp3
B) sp3-sp2
C) sp2-sp2
D) sp2-s
E) sp3-s
Answer: E
Section: 1-12
47) Among the hydrogen halides, the strongest bond is found in ________ and the longest bond
is found in ________.
A) HF, HF
B) HF, HI
C) HI, HF
D) HI, HI
E) HCl, HBr
Answer: B
Section: 1-13
48) Which bond in the following molecule is the shortest?
A) bond 1
B) bond 2
C) bond 3
D) bond 4
E) bond 5
Answer: E
Section: 1-14
49) Which of the following species have tetrahedral bond angles?
A) A, D and E
B) A, D, E and F
C) A and E
D) D only
E) A, B and E
Answer: B
Section: 1-14
50) The carbon-carbon double bond in ethene is ________ and ________ than the carbon-carbon

triple bond in ethyne.
A) stronger; shorter
B) stronger; longer
C) weaker; shorter
D) weaker; longer
E) stronger; more polar
Answer: D
Section: 1-14
51) What is the CNN bond angle in the compound shown below?
A) ~60
B) ~90
C) ~110
D) ~120
E) ~180
Answer: D
Section: 1-14
52) Draw the structure of a molecule which contains only carbon and hydrogen atoms (only three
of which are carbon) and in which two of the carbons are sp2 hybridized and the other is sp
hybridized.
Answer: H2CCCH2
Section: 1-14
53) Why is the CH bond in ethene (H2CCH2) shorter and stronger than the CH bond in
ethane(CH3CH3)?
Answer: The length and strength of a CH bond depends on the hybridization of the carbon
atom. The more s character in the hybrid orbital used by carbon to form the bond, the shorter and
stronger the bond. This is because an s orbital is closer to the nucleus than is a p. Ethene uses
carbon sp2 hybrid orbitals (1/3 s character) to make its carbon-hydrogen bonds while ethane uses
carbon sp3 (1/4 s character).
Section: 1-14
54) Which of the following molecules does not exhibit a net dipole moment of zero?
A) CO2
B) CH4
C) CCl4
D) H2O
E) SO3
Answer: D
Section: 1-15

55) Which of the following molecules has a net dipole moment of zero?
A)
B)
C)
D)
E)
Answer: B
Section: 1-15
56) Which of the following molecules has the smallest dipole moment?
A) Br2
B) NH3
C) HCl
D) HBr
E) HI
Answer: A
Section: 1-15

57) BF3 has a dipole moment of zero. Propose a structure for BF3 that is consistent with this
information.
Answer: BF3 is trigonal planar.
Section: 1-15
58) Draw the Kekul structure and show the direction of the dipole moment for CH2Cl2.
Answer:
Section: 1-15
59) Which of the following is not a conjugate acid-base pair?
A) H2O, HOB) H2O, H3O+
C) HSO4-, H2SO4
D) -OH, O2E) NO3-, NO2Answer: E
Section: 1-16
60) What is the product formed from the following acid-base reaction?
A) CH3O- + +NH4
B) CH2OH + +NH3
C) CH3OH2+ + -NH2
D) CH3NH2 + H2O
E) CH4 + NH2OH
Answer: A
Section: 1-16

61) The conjugate acid of H2O is:
A) H3OB) H3O
C) H3O+
D) HOE) H2O+
Answer: C
Section: 1-16
62) Which of the following ions is the strongest acid?
A) HB) HOC) HSO4D) H2O
E) H3O+
Answer: E
Section: 1-16
63) Which species act as bases in the following reaction?
A) 1 and 2
B) 3 and 4
C) 2 and 4
D) 1 and 3
E) 2 and 3
Answer: C
Section: 1-16
64) What is the conjugate acid of NH3?
A) +NH3
B) -NH
C) +NH4
D) -NH2
E) +NH2
Answer: C
Section: 1-16

65) What is the conjugate acid of CH3NH2?
A) CH3NH3+
B) CH3NHC) NH4+
D) NH2Answer: A
Section: 1-16
66) What is the conjugate base of CH3NH2?
A) CH3NH3+
B) CH3NHC) NH4+
D) NH2Answer: B
Section: 1-16
67) Give the conjugate acid and the conjugate base for HSO4-.
Answer: conjugate acid: H2SO4
conjugate base: SO42Section: 1-16
68) Write a completed equation for the acid-base pair shown below.
HCO2H + -NH2
Answer: HCO2H + -NH2 HCO2- + NH3
Section: 1-16
69) What is the pH of a 0.1 M solution of HCl? (Note: pKa for HCl is -6.)
A) 6
B) -6
C) 1
D) -8
E) -1
Answer: C
Section: 1-17
70) If H2O has a pKa value of 15.7 and HF has a pKa value of 3.2, which is a stronger base, HOor F-? Explain.
Answer: HO- is a stronger base than F- because HF is a stronger acid than H2O, and the
stronger the acid the weaker its conjugate base.
Section: 1-17

71) Which of the following is the strongest acid?
A) CH3OH
B) CH3OH2+
C) H2ND) CH3NH2
E) CH3NH3+
Answer: B
Section: 1-21
72) The pKa of CH3COOH is 4.8 and the pKa of HCOOH is 3.8. Given this information, one
knows that ________.
A) CH3COOH completely ionizes in water
B) HCOOH is a weaker acid than CH3COOH
C) HCOO- is a weaker base than CH3COOD) CH3COOH reacts with HO- while HCOOH does not
E) HCOOH reacts with HO- while CH3COOH does not
Answer: C
Section: 1-21
A) HF
B) H2O
C) : NH3
D) CH4
E) CH3OH
Answer: A
Section: 1-21
A) CH3CH2OH
B) CH3OCH3
C) CH3NHCH3
D) CH3CCH
E) CH3CHCH2
Answer: A
Section: 1-21

75) Consider the set of compounds, NH3, HF, and H2O. Rank these compounds in order of
increasing acidity and discuss your rationale.
Answer: NH3 < H2O < HF
When determining relative acidity, it is often useful to look at the relative basicity of the
conjugate bases. The stronger the acid, the weaker (more stable, less reactive) the conjugate base.
In this case, one would look at the relative basicity of F-, OH-, and NH2-. The relative strengths
of these species can be gauged based on the electronegativity of the charged atom in each base.
Since fluorine is the most electronegative, F- is the most stable, least reactive base in the group.
This means that its conjugate acid, HF, is the strongest.
Section: 1-21
A) I
B) II
C) III
D) IV
E) V
Answer: E
Section: 1-22
77) Explain why :NF3 is a weaker base than :NH3.
Answer: Fluorine has an electron withdrawing effect that reduces the availability of the pair of
electrons on nitrogen. Thus the basicity of :NF3 is less than that of :NH3.
Section: 1-22

78) Would you predict trifluoromethanesulfonic acid, CF3SO3H, to be a stronger or weaker acid
than methanesulfonic acid, CH3SO3H? Explain your reasoning.
Answer: Trifluoromethanesulfonic acid is a stronger acid. Compare the strengths of the
conjugate bases and remember that the weaker the base, the stronger the conjugate acid. In the
case of the trifluoro derivative, the presence of the highly electronegative fluorine atoms serves
to delocalize the negative charge to a greater extent. This additional delocalization makes
trifluoromethanesulfonate a weaker base.
Section: 1-22
79) Which of the following anions, CH3CHBrCO2- or CH3CHFCO2- is the stronger base?
Explain your choice.
Answer: CH3CHBrCO2- is the stronger base. The more electronegative F atom can more
effectively delocalize the negative charge via induction. This greater delocalization stabilizes
CH3CHFCO2- relative to CH3CHBrCO2- and makes it a weaker base.
Section: 1-22
80) The pKa of CH3COOH is 4.8. If the pH of an aqueous solution of CH3COOH and
CH3COO- is 4.8, then one knows ________.
A) CH3COOH is completely ionized
B) [CH3COOH] > [CH3COO-]
C) [CH3COOH] = [CH3COO-]
D) [CH3COOH] < [CH3COO-]
E) CH3COOH is completely unionized
Answer: C
Section: 1-25
81) When a small amount of hexanoic acid [CH3(CH2)4CO2H, pKa~4.8], is added to a
separatory funnel which contains the organic solvent diethyl ether and water with a pH of 2.0, it
is found mainly in the ________ phase as ________.
A) ether; CH3(CH2)4CO2B) water; CH3(CH2)4CO2C) ether; CH3(CH2)4CO2H
D) water; CH3(CH2)4CO2H
E) none of the above
Answer: C
Section: 1-25

82) When a small amount of hexanoic acid [CH3(CH2)4CO2H, pKa~4.8], is added to a
separatory funnel which contains the organic solvent diethyl ether and water with a pH of 12.0, it
is found mainly in the ________ phase as ________.
A) ether; CH3(CH2)4CO2B) water; CH3(CH2)4CO2C) ether; CH3(CH2)4CO2H
D) water; CH3(CH2)4CO2H
E) none of the above
Answer: B
Section: 1-25
83) At what pH will 25% of a compound with a pKa of 5.3 be in its basic form?
Answer: 4.8
Section: 1-25
84) The amino acid glycine (H3N+CH2CO2H) has two acidic Hs, one with pKa = 2.34 and the
other with pKa=9.60. Draw the structure of the form of glycine that predominates at a pH of 12.
Answer:
Section: 1-25
85) Buffering is used to maintain the pH of human blood in the relatively narrow 7.3 - 7.4 range.
What acid/base pair serves to buffer the blood?
A) H2O / HOB) H3O+ / H2O
C) H2CO3 / HCO3D) NH4+ / NH3
E) HCl / ClAnswer: C
Section: 1-26
86) Explain why AlCl3 is a Lewis acid.
Answer: A Lewis acid is an electron pair acceptor. Aluminum in AlCl3 has an empty p orbital
that can accommodate the pair of electrons provided by a Lewis base.
Section: 1-27

87) Give the electronic configuration for N-3.
A) 1s22s2
B) 1s22s22p3
C) 1s22s22p4
D) 1s22s22p6
E) 1s22s22p63s1
Answer: D
Section: 1-2
88) Give the electronic configuration for Ca+2.
Answer: 1s22s22p63s23p6
Section: 1-2
89) Identify the least electronegative atom.
A) P
B) Na
C) I
D) B
E) O
Answer: B
Section: 1-3
90) Give the number of nonbonding pairs of electrons in H2NOH.
A) 0
B) 1
C) 2
D) 3
E) 4
Answer: D
Section: 1-3
91) Give the formal charge on nitrogen in NH4.
A) -2
B) -1
C) 0
D) +1
E) +2
Answer: D
Section: 1-4

92) Determine the number of pi bonds in CH3CN.
A) 0
B) 1
C) 2
D) 3
E) 4
Answer: C
Section: 1-9
93) Give the numbering of nonbonding electron pairs, bonding electron pairs, pi bonds, and
sigma bonds in CO2.
Answer: 4 nonbonding electron pairs, 4 bonding electrons pairs , 2 pi bonds, 2 sigma bonds
Section: 1-14
94) Give the shape of the methyl radical.
A) trigonal pyramidal
B) tetrahedral
C) bent
D) linear
E) trigonal planar
Answer: E
Section: 1-10
95) Identify the hybridization of carbon in H2CO.
A) sp
B) sp2
C) sp3
D) sp4
E) s3p
Answer: B
Section: 1-14
96) Give the approximate bond angle around the carbon in H2CO.
A) 60
B) 90
C) 109.5
D) 120
E) 180
Answer: D
Section: 1-14

97) Identify the hybridization of the oxygen in CH3OCH3.
A) sp
B) sp2
C) sp3
D) sp4
E) sp5
Answer: C
Section: 1-14
98) Give the hybridizations of the carbons, from left to right, in CH3CH=CHCl.
Answer: sp3, sp2, sp2
Section: 1-14
99) Give the hybridization, shape, and bond angle for the carbon in CO2.
Answer: sp, linear, 180
Section: 1-14
100) Give the hybridization, shape, and bond angle for each carbon in CH3CN.
Answer: CH3 - sp3, tetrahedral, 109.5; C - sp, linear, 180
Section: 1-14
101) Identify the compound with the weakest bond.
A) H2
B) HF
C) HCl
D) HBr
E) HI
Answer: E
Section: 1-14
102) Identify the compound(s) that have a dipole moment.
A) CH3NH2
B) CO2
C) CH3OCH3
D) (CH3)2C=C(CH3)2
E) BCl3
Answer: A, C
Section: 1-15

103) Identify the compound with the highest pKa.
A) CH3NH2
B) CH3OH
C) CH3COOH
D) H2O
E) CH3NH3+
Answer: A
Section: 1-21
104) Identify the compound with the highest pKa.
A) CH3CH3
B) HCCH
C) CH2CH2
D) CH3OH
E) CH3NH2
Answer: A
Section: 1-21
105) Identify the most acidic carboxylic acid.
A) ICH2COOH
B) BrCH2COOH
C) CH3COOH
D) FCH2COOH
E) ClCH2COOH
Answer: D
Section: 1-22
106) Draw a resonance contributor and the resonance hybrid for HOCO2-.
Answer: resonance contributor:
resonance hybrid:
Section: 1-23

107) How many carbon-carbon s bonds are in the molecule shown?
A) 1
B) 2
C) 3
D) 4
Answer: B
Section: 1-7
108) The hydrogenhalogen bond becomes ________ and ________ as the size (atomic weight)
of the halogen increases.
A) longer, weaker
B) longer, stronger
C) shorter, weaker
D) shorter, stronger
Answer: A
Section: 1-13

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