Deck 1: Carbon Compounds and Chemical Bonds
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Deck 1: Carbon Compounds and Chemical Bonds
1
In which of the following does the central atom have 2 pairs of non-bonding electrons?
A) O3
B) CO2
C) CO3 2-
D) NH4 +
E) H2S
A) O3
B) CO2
C) CO3 2-
D) NH4 +
E) H2S
H2S
2
Which compound is not a constitutional isomer of the others? 
A) I
B) II
C) III
D) IV
E) All of the above are isomers of each other.

A) I
B) II
C) III
D) IV
E) All of the above are isomers of each other.
I
3
Select the least electronegative element from the list below:
A) P
B) N
C) Mg
D) Si
E) K
A) P
B) N
C) Mg
D) Si
E) K
K
4
Select the most electronegative element from the list below:
A) H
B) O
C) N
D) B
E) C
A) H
B) O
C) N
D) B
E) C
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5
How many sigma 1s-2sp3 bonds are there in ethane?
A) 7
B) 6
C) 5
D) 3
E) 1
A) 7
B) 6
C) 5
D) 3
E) 1
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6
Which of the following structures represent compounds that are constitutional isomers of each other? 
A) I and II
B) I and III
C) I,II,and III
D) I,II,III,and IV
E) II and III

A) I and II
B) I and III
C) I,II,and III
D) I,II,III,and IV
E) II and III
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7
Which of the following represent pairs of constitutional isomers?
A)

B)

C)

D) None of these pairs
E) All of these pairs
A)

B)

C)

D) None of these pairs
E) All of these pairs
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8
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
A) Berzelius
B) Arrhenius
C) Kekule
D) Wohler
E) Lewis
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9
Which of the following is the Lewis structure for CH3CO2H?
A)

B)

C)

D)

E)

A)

B)

C)

D)

E)

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10
Consider the following: CH3CH2CH=CHCH2CH3
CH3CH2CH2CH2CH=CH2
I
II
CH3CH=CHCH2CH2CH3
CH2=CHCH2CH2CH2CH3
III
IV
Which two structures represent the same compound?
A) I and II
B) II and III
C) I and III
D) II and IV
E) None of these
CH3CH2CH2CH2CH=CH2
I
II
CH3CH=CHCH2CH2CH3
CH2=CHCH2CH2CH2CH3
III
IV
Which two structures represent the same compound?
A) I and II
B) II and III
C) I and III
D) II and IV
E) None of these
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11
Which of the following is a set of constitutional isomers? 
A) I and II
B) II and III
C) I,II,and III
D) II,III,and IV
E) I,III,and IV

A) I and II
B) II and III
C) I,II,and III
D) II,III,and IV
E) I,III,and IV
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12
Which compound is not a constitutional isomer of the others? 
A) I
B) II
C) III
D) IV
E) All of the above are isomers of each other.

A) I
B) II
C) III
D) IV
E) All of the above are isomers of each other.
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13
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
A) Structural isomers
B) Resonance structures
C) Functional isomers
D) Empirical isomers
E) Constitutional isomers
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14
Which of the following is the Lewis structure for CH3CH2O2H?
A)

B)

C)

D)

E)

A)

B)

C)

D)

E)

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15
Considering Lewis structures,which of these compounds possesses a single unpaired electron?
A) N2
B) N2O
C) NO
D) N2O4
E) O2
A) N2
B) N2O
C) NO
D) N2O4
E) O2
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16
Which of these is a correct electron-dot representation of the nitrite ion,NO2-? 
A) I
B) II
C) III
D) IV
E) V

A) I
B) II
C) III
D) IV
E) V
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17
Which is NOT a correct Lewis structure?
A)

B)

C)

D)

E) None of these
A)

B)

C)

D)

E) None of these
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18
The greatest degree of ionic character is anticipated for the bond between:
A) H and C
B) H and Cl
C) C and Cl
D) H and Br
E) Br and Cl
A) H and C
B) H and Cl
C) C and Cl
D) H and Br
E) Br and Cl
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19
Which compound is not a constitutional isomer of the others? 
A) I and II
B) II
C) III
D) IV and V
E) All of the above are isomers of each other.

A) I and II
B) II
C) III
D) IV and V
E) All of the above are isomers of each other.
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20
Which of the following represent a pair of constitutional isomers?
A)

B) CH3CH=CH2 and CH2=CHCH3
C)

D)

E) More than one of these
A)

B) CH3CH=CH2 and CH2=CHCH3
C)

D)

E) More than one of these
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21
Which of the following species is/are a resonance form(s)of the species in the box? 
A) I and II
B) I and III
C) III and IV
D) III
E) More than two of them are correct resonance forms.

A) I and II
B) I and III
C) III and IV
D) III
E) More than two of them are correct resonance forms.
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22
In which structure(s)below does the oxygen have a formal charge of +1?
s
A) I only
B) II only
C) I and III
D) I and IV
E) I,III,and IV
sA) I only
B) II only
C) I and III
D) I and IV
E) I,III,and IV
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23
What is the formal charge on carbon in the following structure? 
A) +2
B) +1
C) 0
D) -1
E) -2

A) +2
B) +1
C) 0
D) -1
E) -2
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24
Which of the following species is/are not a resonance form(s)of the anionic species in the box? 
A) I
B) II and III
C) III and IV
D) I and IV
E) I and III

A) I
B) II and III
C) III and IV
D) I and IV
E) I and III
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25
Which compound contains a nitrogen atom with a formal positive charge? 
A) I
B) II
C) III
D) More than one of the above
E) None of the above

A) I
B) II
C) III
D) More than one of the above
E) None of the above
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26
What is the formal charge on oxygen in the following structure? 
A) +2
B) +1
C) 0
D) -1
E) -2

A) +2
B) +1
C) 0
D) -1
E) -2
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27
Expansion of the valence shell to accommodate more than eight electrons is possible with:
A) Fluorine
B) Nitrogen
C) Carbon
D) Sulfur
E) Beryllium
A) Fluorine
B) Nitrogen
C) Carbon
D) Sulfur
E) Beryllium
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28
In which structure(s)below does nitrogen have a formal charge of +1? 
A) I
B) II and IV
C) III and V
D) I and V
E) V

A) I
B) II and IV
C) III and V
D) I and V
E) V
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29
Which of the following molecules or ions has a nitrogen with a formal charge of -1? (Charges on ions have been omitted. )
A)

B)

C)

D)

E)

A)

B)

C)

D)

E)

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30
Listed below are electron dot formulas for several simple molecules and ions.All valence electrons are shown;however,electrical charges have been omitted deliberately.
Which of the structures actually bear(s)a positive charge?
A) I
B) II
C) III
D) III & V
E) IV & V
Which of the structures actually bear(s)a positive charge?A) I
B) II
C) III
D) III & V
E) IV & V
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31
The formal charge on sulfur in sulfuric acid is: 
A) 0
B) -1
C) +1
D) -2
E) +2

A) 0
B) -1
C) +1
D) -2
E) +2
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32
Listed below are electron dot formulas for several simple molecules and ions.All valence electrons are shown;however,electrical charges have been omitted deliberately.
Which of the structures is negatively charged?
A) I
B) II
C) III
D) IV
E) V
Which of the structures is negatively charged?A) I
B) II
C) III
D) IV
E) V
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33
What is the formal charge on oxygen in the following structure? 
A) +2
B) +1
C) 0
D) -1
E) -2

A) +2
B) +1
C) 0
D) -1
E) -2
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34
Which of the following is an ion with a single negative charge?
A)

B)

C)

D) All of these
E) None of these
A)

B)

C)

D) All of these
E) None of these
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35
Which of the following pairs are NOT resonance structures?
A)

B)

C)

D) Each of these pairs represents resonance structures.
E) None of these pairs represents resonance structures.
A)

B)

C)

D) Each of these pairs represents resonance structures.
E) None of these pairs represents resonance structures.
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36
Which of the following species is a resonance form of the species in the box? 
A) I
B) II
C) III
D) IV
E) None of the above are correct resonance forms.

A) I
B) II
C) III
D) IV
E) None of the above are correct resonance forms.
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37
In which of these cases does the central atom have a zero formal charge?
A) HFH
B)

C)

D)

E)

A) HFH
B)

C)

D)

E)

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38
Which structure(s)contain(s)an oxygen that bears a formal charge of +1? 
A) I and II
B) III and IV
C) V
D) II
E) I and V

A) I and II
B) III and IV
C) V
D) II
E) I and V
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39
Which of the following species is not a resonance form of the following species? 
A)

B)

C)

D)

E)


A)

B)

C)

D)

E)

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40
Which of the following species is/are a resonance form(s)of the species in the box? 
A) I and II
B) II and III
C) III
D) II
E) More than two of them are correct resonance forms.

A) I and II
B) II and III
C) III
D) II
E) More than two of them are correct resonance forms.
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41
Which of the structures below is not expected to contribute to the CO2 resonance hybrid?
A)

B)

C)

D)

E)

A)

B)

C)

D)

E)

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42
Which of the following structures is/are not a resonance form of the following species? 
A)

B)

C)

D)

E) None of the above are correct resonance forms.

A)

B)

C)

D)

E) None of the above are correct resonance forms.
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43
How many resonance structures can be written for the NO3- ion in which the nitrogen atom bears a formal charge of +1?
A) 1
B) 2
C) 3
D) 4
E) 5
A) 1
B) 2
C) 3
D) 4
E) 5
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44
Which of the following species is a resonance form of the following species? 
A)

B)

C)

D)

E) All the above are correct resonance forms.

A)

B)

C)

D)

E) All the above are correct resonance forms.
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45
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
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
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46
In quantum mechanics a node (nodal surface or plane)is:
A) a place where is negative.
B) a place where is positive.
C) a place where = 0.
D) a place where 2 is large.
E) a place where 2 is negative.
A) a place where is negative.
B) a place where is positive.
C) a place where = 0.
D) a place where 2 is large.
E) a place where 2 is negative.
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47
Which of the following species is/are not a resonance form(s)of the species in the box? 
A) I
B) II
C) III
D) IV
E) More than two of them are incorrect resonance forms.

A) I
B) II
C) III
D) IV
E) More than two of them are incorrect resonance forms.
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48
Which of the following could not be a resonance structure of CH3NO2?
A)

B)

C)

D)

E) Both C and D
A)

B)

C)

D)

E) Both C and D
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49
Which of the following species exhibits resonance stabilization?
A) H2SO4
B) O3
C) CO2
D) CCl4
E) None of the species above exhibit resonance.
A) H2SO4
B) O3
C) CO2
D) CCl4
E) None of the species above exhibit resonance.
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50
Which of the following species contributes more to the overall hybrid for the species in the box? 
A) I
B) II
C) III
D) IV
E) The one in the box.

A) I
B) II
C) III
D) IV
E) The one in the box.
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51
Which of the following species contributes more to the overall hybrid for the species in the box? 
A) I
B) II
C) III
D) IV
E) The one in the box.

A) I
B) II
C) III
D) IV
E) The one in the box.
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52
Which of the following species contributes more to the overall hybrid for the species in the box? 
A) I
B) II
C) III
D) IV
E) The one in the box.

A) I
B) II
C) III
D) IV
E) The one in the box.
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53
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
A) 1
B) 2
C) 3
D) 4
E) 5
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54
Which of the following species is/are not a resonance form(s)of the species in the box? 
A) I and II
B) II and III
C) III and IV
D) I and IV
E) II and IV

A) I and II
B) II and III
C) III and IV
D) I and IV
E) II and IV
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55
Which of the following species are resonance forms of the species in the box? 
A) I and III
B) I and II
C) III and IV
D) II and IV
E) All of the above are correct resonance forms.

A) I and III
B) I and II
C) III and IV
D) II and IV
E) All of the above are correct resonance forms.
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56
Which of the following species contributes more to the overall hybrid for the species in the box? 
A) I
B) II
C) III
D) IV
E) The one in the box.

A) I
B) II
C) III
D) IV
E) The one in the box.
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57
Which of the following species contributes more to the overall hybrid for the species in the box? 
A) I
B) II
C) III
D) IV
E) The one in the box.

A) I
B) II
C) III
D) IV
E) The one in the box.
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58
Which of the following species contributes more to the overall hybrid for the species in the box? 
A) I
B) II
C) III
D) IV
E) The one in the box.

A) I
B) II
C) III
D) IV
E) The one in the box.
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59
Which of the following species is/are not a resonance form(s)of the species in the box? 
A) I
B) II
C) III
D) IV
E) More than two of them are incorrect resonance forms.

A) I
B) II
C) III
D) IV
E) More than two of them are incorrect resonance forms.
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60
Which principle(s)or rule(s)must be used to determine the correct electronic configuration for carbon in its ground state?
A) Aufbau Principle
B) Hund's Rule
C) Pauli Exclusion Principle
D) (A)and (B)only
E) All three
A) Aufbau Principle
B) Hund's Rule
C) Pauli Exclusion Principle
D) (A)and (B)only
E) All three
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61
Which of the following contains an sp2-hybridized carbon?
A) CH4
B) CH3: -
C) CH3CH3
D) CH3+
E) HC CH
A) CH4
B) CH3: -
C) CH3CH3
D) CH3+
E) HC CH
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62
Select the hybridized atomic orbital. 
A) I
B) II
C) III
D) IV
E) V

A) I
B) II
C) III
D) IV
E) V
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63
Identify the atomic orbitals in the C-C sigma bond in ethyne.
A) (2sp2,2sp2)
B) (2sp3,2sp3)
C) (2sp,2sp)
D) (2p,2p)
E) (2sp,1s)
A) (2sp2,2sp2)
B) (2sp3,2sp3)
C) (2sp,2sp)
D) (2p,2p)
E) (2sp,1s)
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64
Which molecule has the shortest carbon-carbon single bond? 
A) I
B) II
C) III
D) IV
E) V

A) I
B) II
C) III
D) IV
E) V
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65
How many s-sp3 bonds are there in the following substance? 
A) 3
B) 8
C) 12
D) 13
E) 16

A) 3
B) 8
C) 12
D) 13
E) 16
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66
What point on the potential energy diagram below represents the most stable state for the hydrogen molecule? 
A) I
B) II
C) III
D) IV
E) V

A) I
B) II
C) III
D) IV
E) V
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67
cis-trans : isomerism is possible only in the case of:
A) CH2=CBr2
B) CH2=CHBr
C) BrCH=CHBr
D) Br2C=CHBr
E) Br2C=CBr2
A) CH2=CBr2
B) CH2=CHBr
C) BrCH=CHBr
D) Br2C=CHBr
E) Br2C=CBr2
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68
According to molecular orbital theory,which molecule could not exist?
A) H2
B) He2
C) Li2
D) F2
E) N2
A) H2
B) He2
C) Li2
D) F2
E) N2
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69
When the 1s orbitals of two hydrogen atoms combine to form a hydrogen molecule,how are the electrons distributed in the resulting molecular orbitals?
A) 2 electrons in the bonding molecular orbital
B) 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 non-bonding molecular orbital
E) 2 electrons in the antibonding molecular orbital
A) 2 electrons in the bonding molecular orbital
B) 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 non-bonding molecular orbital
E) 2 electrons in the antibonding molecular orbital
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70
What is the hybridization of the C indicated with the arrow? 
A) sp3
B) sp2
C) sp
D) s
E) p

A) sp3
B) sp2
C) sp
D) s
E) p
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71
How many 2p atomic orbitals from boron must be mixed with a 2s atomic orbital to yield the bonding hybrid atomic orbitals in BF3?
A) 1
B) 2
C) 3
D) 4
E) 5
A) 1
B) 2
C) 3
D) 4
E) 5
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72
Which compound has the shortest carbon-carbon bond(s)?
A) CH3CH3
B) CH2=CH2
C) HC CH
D) CH3CH2CH3
E) All carbon-carbon bonds are the same length.
A) CH3CH3
B) CH2=CH2
C) HC CH
D) CH3CH2CH3
E) All carbon-carbon bonds are the same length.
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73
Which is the shortest of the carbon-carbon single bonds indicated by arrows in the following compounds?
A)

B)

C)

D)

E)

A)

B)

C)

D)

E)

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74
Which of the following species contributes more to the overall hybrid for the species in the box? 
A) I
B) II
C) III
D) IV
E) The one in the box.

A) I
B) II
C) III
D) IV
E) The one in the box.
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75
Identify the atomic orbital.The lone pair electrons on the B atom are contained in: 
A) 2sp2
B) 2sp3
C) 2p
D) 2s
E) There are no lone pair electrons on B

A) 2sp2
B) 2sp3
C) 2p
D) 2s
E) There are no lone pair electrons on B
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76
What is the geometry of the C indicated with the arrow? 
A) tetrahedral
B) trigonal pyramidal
C) linear
D) bent
E) trigonal planar

A) tetrahedral
B) trigonal pyramidal
C) linear
D) bent
E) trigonal planar
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77
The C4-C5 carbon-carbon bond in the following molecule results from the overlap of which orbitals ( in the order C4-C5)? 
A) sp-sp2
B) sp-sp3
C) sp2-sp2
D) sp2-sp3
E) sp3-sp2

A) sp-sp2
B) sp-sp3
C) sp2-sp2
D) sp2-sp3
E) sp3-sp2
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78
According to molecular orbital theory,in the case of a carbon-carbon double bond,the carbon-carbon bonding electrons of higher energy occupy this molecular orbital:
A) " bonding MO"
B) " bonding MO"
C) " * antibonding MO"
D) " * antibonding MO"
E) " * bonding MO"
A) " bonding MO"
B) " bonding MO"
C) " * antibonding MO"
D) " * antibonding MO"
E) " * bonding MO"
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79
Consider the following: 
Which structures can exist as cis-trans : isomers?
A) I and II
B) I and III
C) I and IV
D) II and III
E) I alone

Which structures can exist as cis-trans : isomers?
A) I and II
B) I and III
C) I and IV
D) II and III
E) I alone
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80
Identify the atomic orbitals in the C-H sigma bond in acetylene.
A) (2sp2,1s)
B) (2sp3,2sp3)
C) (2sp,2sp)
D) (2p,2p)
E) (2sp,1s)
A) (2sp2,1s)
B) (2sp3,2sp3)
C) (2sp,2sp)
D) (2p,2p)
E) (2sp,1s)
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