Deck 2: Acids and Bases; Functional Groups

Question 1

The electron density at any point is proportional to the ________ of the electron wave at that point.

Answer 1

square of the wave function

Question 2

How many π bonds are present in the molecule shown?

A) 0
B) 1
C) 2
D) 4
E) 6

Answer 2

2

Question 3

How many π bonds are present in the molecule shown?

A) 0
B) 1
C) 3
D) 4
E) 6

Answer 3

3

Question 4

What kind of molecular orbital (σ, σ^*, π, or π^*) results when the two atomic orbitals shown below interact in the manner indicated?

Question 5

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.

Question 6

What kind of molecular orbital (σ, σ^*, π, or π^*) results when the two atomic orbitals shown below interact in the manner indicated?

Question 7

What kind of molecular orbital (σ, σ^*, π, or π^*) results when the two atomic orbitals shown below interact in the manner indicated?

Question 8

When orbitals on different atoms interact, ________ are produced.

Question 9

An orbital can be described by its ________, which is the mathematical description of the shape of the electron wave as it oscillates.

Question 10

What kind of molecular orbital (σ, σ^*, π, or π^*) results when the two atomic orbitals shown below interact in the manner indicated?

Question 11

How many carbon-carbon σ bonds are present in the molecule shown?

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

Question 12

Two p orbitals can overlap to form a σ molecular orbital. How many nodes are present in this σ molecular orbital?

A) 0
B) 1
C) 2
D) 3

Question 13

How many carbon-carbon σ bonds are present in the molecule shown?

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

Question 14

A ________ bond results when parallel p orbitals overlap sideways.

Question 15

How many carbon-carbon σ bonds are present in the molecule shown?

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

Question 16

If a compound, C₅H₇NO, contains 1 ring, how many pi bonds are there in this compound?

A) 0
B) 1
C) 2
D) 3

Question 17

Two p orbitals can overlap to form a σ* molecular orbital. How many nodes are present in this σ* molecular orbital?

A) 0
B) 1
C) 2
D) 3

Question 18

Which of the following statements about π molecular orbitals is/are correct?

A) π molecular orbitals are cylindrically symmetric.
B) Most of the electron density in a π molecular orbital is centered above and below the internuclear axis.
C) When two atoms are connected by a double bond, both of these bonds are π bonds.
D) Both statements B and C are correct.
E) Statements A, B, and C are all correct.

Question 19

Which atomic orbital combination would result in a molecular sigma bond?

A)
B)
C)
D)

Question 20

What kind of molecular orbital (σ, σ^*, π, or π^*) results when the two atomic orbitals shown below interact in the manner indicated?

Question 21

What two hybrid atomic orbitals overlap to form the C-C σ bond in acetonitrile, CH₃C≡N?

Question 22

Shown below is one of the sex pheremones from the butterfly family. How many sp² hybridized carbon atoms are present in this molecule?

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

Question 23

In the structure below, the hybridization of the oxygen is ________ and the C-O-C bond angle is ________.

A) sp²; 120°
B) sp²; <109.5°
C) sp³; 120°
D) sp³; <109.5°
E) sp; 120°

Question 24

Draw a three-dimensional model of methanol, CH₃OH, including lone pairs of electrons using wedges, dashes and straight lines.

Question 25

Choose the term below which best describes the geometry of acetylene (HCCH).

A) trigonal bipyramidal
B) trigonal
C) tetrahedral
D) square planar
E) linear

Question 26

Choose the correct hybridization for the atom indicated in the molecule below.
CH₃CH₂CH₂CH₃
↑

A) sp
B) sp²
C) sp³
D) none of the above

Question 27

In the structure below, the sigma bond of the carbonyl is formed from the overlap of a(n) ________ atomic orbital of carbon and a(n) ________ atomic orbital of oxygen.

A) sp, sp²
B) sp³, sp²
C) sp², sp²
D) p, p

Question 28

What is the approximate value of the CCC bond angle in CH₃CH₂CH₂OH?

Question 29

What two hybrid atomic orbitals overlap to form the C-C σ bond in allene, H₂C=C=CH₂?

Question 30

Choose the correct hybridization for the atom indicated in the molecule below.
CH₃CH₂CH₂CH₃
↑

A) sp
B) sp²
C) sp³
D) none of the above

Question 31

The HCH bond angle in allene (H₂CCCH₂) is ________.

Question 32

Vildagliptin is a recently released antidiabetic drug (J. Med. Chem. 2010, 7902). How many elements of unsaturation are in Vildagliptin?

A) 4
B) 5
C) 6
D) 7

Question 33

Shown below is one of the sex pheremones from the butterfly family. How many sp³ hybridized carbon atoms are present?

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

Question 34

What is the approximate value of the CCC bond angle in CH₃C≡CCH₃?

Question 35

Circle the coplanar atoms in 1-ethylcyclopentene shown below.

Question 36

Based on the structure below, what is the value for the H-N-CH₃ bond angle?

A) 60 degrees
B) 90 degrees
C) 109 degrees
D) 120 degrees

Question 37

Complete the structure of methyl azide by adding any necessary formal charges.

Question 38

What is the approximate value of any HCC bond angle in H₂C=CHCCl₃?

Question 39

Shown below is one of the sex pheremones from the butterfly family. How many sp hybridized carbon atoms are present in this molecule?

A) 0
B) 1
C) 2
D) 3
E) 5

Question 40

What two hybrid atomic orbitals overlap to form the C-C σ bond in acetaldehyde, CH₃CHO?

Question 41

The CCN bond angle in acrylonitrile (CH₂=CHCN) is approximately ________.

A) 60°
B) 90°
C) 109.5°
D) 120°
E) 180°

Question 42

Choose the correct hybridization for the atom indicated in the molecule below.
(CH₃)₂CHCN
↑

A) sp
B) sp²
C) sp³
D) none of the above

Question 43

Acrylonitrile (CH₂=CHCN) contains ________ σ bonds and ________ π bonds.

A) 4; 1
B) 6; 3
C) 4; 3
D) 6; 1
E) 2; 0

Question 44

Choose the correct hybridization for the atom indicated in the molecule below.
(CH₃)₂CHCN
↑

A) sp
B) sp²
C) sp³
D) none of the above

Question 45

Choose the correct hybridization for the atom indicated in the molecule below.

A) sp
B) sp²
C) sp³
D) none of the above

Question 46

How many σ bonds does the compound shown contain?

A) 3
B) 5
C) 9
D) 10
E) 11

Question 47

There is one more important resonance form for the structure below. Draw it and then indicate the hybridization of all of the non-H atoms.

Question 48

The CCO bond angle in acetone (CH₃COCH₃) is ________.

Question 49

What is the hybridization of the nitrogen atom in the molecule below?

A) s
B) sp
C) sp²
D) sp³
E) none of the above

Question 50

What is the approximate CCC bond angle in the compound below?

A) 60°
B) 90°
C) 109.5°
D) 120°
E) 180°

Question 51

Which of the following statements concerning the cyclic molecule shown is not true?

A) It contains a π molecular orbital formed by the overlap of a carbon p atomic orbital with an oxygen p atomic orbital.
B) It contains a σ molecular orbital formed by the overlap of two carbon sp² hybrid atomic orbitals.
C) It contains a σ molecular orbital formed by the overlap of two carbon sp³ hybrid atomic orbitals.
D) It contains a π molecular orbital formed by the overlap of two carbon p atomic orbitals.
E) It contains a σ molecular orbital formed by the overlap of a carbon p atomic orbital with an oxygen sp³ atomic orbital.

Question 52

The structure of uracil is shown below. What is the hybridization of the nitrogens?

Question 53

The molecule shown below contains ________ pi bonds and ________ sigma bonds.

Question 54

The HNC bond angle in the cation [CH₂NH₂]⁺ is approximately ________.

A) 60°
B) 90°
C) 109.5°
D) 120°
E) 180°

Question 55

Which of the labeled atoms in the following structure are sp² hybridized?

A) 1 & 4
B) 2 & 5
C) 2 & 4
D) 2 & 3
E) 2, 3, & 4

Question 56

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°

Question 57

Choose the correct hybridization for the atom indicated in the molecule below.

A) sp
B) sp²
C) sp³
D) none of the above

Question 58

The structure of uracil is shown below. What is the molecular shape of the nitrogens?

Question 59

The HCN bond angle in hydrogen cyanide (HCN) is ________.

Question 60

The hybridization of the nitrogen in the molecule shown below is sp². Briefly explain why.

Question 61

Choose the correct hybridization for the atom indicated in the molecule below.

A) sp
B) sp²
C) sp³
D) none of the above

Question 62

Which of the following compounds is not a constitutional isomer of a compound with an empirical formula C₃H₇O and a formula mass of 118.164?

A)
B)
C)
D)
E)

Question 63

Provide the hybridization of oxygen in acetaldehyde (CH₃CHO) and estimate the OCH bond angle.

Question 64

Are the two compounds shown below best described as cis-trans isomers, constitutional isomers, or not isomeric?

Question 65

Boron trifluoride (BF₃) is a molecule in which the boron atom is ________ hybridized and the FBF bond angle is ________.

Question 66

Structures which differ only in rotations about a single bond are called ________.

Question 67

Explain why the free rotation about the carbon-carbon bond in CH₃CH₃ is not present in

Question 68

From a molecular orbital perspective, why is there relatively free rotation about the carbon-carbon bond of ethane (CH₃CH₃)?

Question 69

What hybrid atomic orbitals are overlapping to form the carbon-oxygen σ bond in acetaldehyde (CH₃CHO)?

Question 70

Provide the skeletal structures of the five constitutional isomers with molecular formula C₆H₁₄.

Question 71

Are the two compounds shown below best described as cis-trans isomers, constitutional isomers, or not isomeric?

Question 72

The molecule shown below contains ________ sigma bonds and ________ pi bonds.

Question 73

Choose the correct hybridization for the atom indicated in the molecule below.

A) sp
B) sp²
C) sp³
D) none of the above

Question 74

Are the two compounds shown below best described as cis-trans isomers, constitutional isomers, or not isomeric?

Question 75

From a molecular orbital perspective why isn't there relatively free rotation about the carbon-carbon double bond in ethene (CH₂=CH₂)?

Question 76

Which of the following best describes the relationship between the two structures shown?

A) They represent the same compound.
B) They represent different compounds that are constitutional isomers.
C) They represent different compounds that are geometric isomers.
D) They represent different compounds that are alkenes.
E) They represent different compounds that are alkanes.

Question 77

Are the two compounds shown below best described as cis-trans isomers, constitutional isomers, or not isomeric?

Question 78

Provide the hybridization of oxygen in dimethyl ether (CH₃OCH₃) and estimate the COC bond angle.

Question 79

The synthetic steroid RU-486 is shown below. How many pi bonds does RU-486 contain?

Question 80

Are the two compounds shown below best described as cis-trans isomers, constitutional isomers, or not isomeric?