Deck 5: Alkenes: Bonding, Nomenclature, and Properties

Question 1

What is the approximate value of the C-C-C bond angle in propene?

A)90 ^$\circ$
B)109 ^$\circ$
C)120 ^$\circ$
D)180 ^$\circ$

Answer 1

120 ^$\circ$

Question 2

What is the hybridization of carbon atoms labeled i - iii in the following structure?

A)i = sp²; ii = sp²; iii = sp²
B)i = sp; ii = sp; iii = sp³
C)i = sp²; ii = sp; iii = sp³
D)i = sp²; ii = sp²; iii = sp³

Answer 2

i = sp²; ii = sp²; iii = sp³

Question 3

What is the index of hydrogen deficiency of a compound with a molecular formula of C₅H₁₀?

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

Answer 3

1

Question 4

What type of molecular orbital is formed by the overlap of atomic orbitals shown?

A)" $\sigma$ bonding"
B)" $\sigma$ antibonding"
C)" $\pi$ bonding"
D)" $\pi$ antibonding"

Question 5

What is the approximate value of the length of the carbon-carbon bond in ethene?

A)121 pm
B)134 pm
C)142 pm
D)154 pm

Question 6

What is the index of hydrogen deficiency of a compound with a molecular formula of C₆H₁₅N?

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

Question 7

What is the index of hydrogen deficiency of a compound with a molecular formula of C₆H₈?

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

Question 8

What is the approximate value of the H-C-H bonds angle in ethene?

A)90 ^$\circ$
B)109 ^$\circ$
C)120 ^$\circ$
D)180 ^$\circ$

Question 9

Which of the following does not correspond to a molecular formula of a neutral compound?

A)C₆H₉NO₂
B)C₅H₇N₂O₂
C)C₈H₁₂O₃
D)C₇H₇N

Question 10

What is the index of hydrogen deficiency of a compound with a molecular formula of C₆H₁₂N₂?

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

Question 11

What type of molecular orbital is formed by the overlap of atomic orbitals shown?

A)" $\sigma$ bonding"
B)" $\sigma$ antibonding"
C)" $\pi$ bonding"
D)" $\pi$ antibonding"

Question 12

What type of molecular orbital is formed by the overlap of atomic orbitals shown?

A)" $\sigma$ bonding"
B)" $\sigma$ antibonding"
C)" $\pi$ bonding"
D)" $\pi$ antibonding"

Question 13

Which of the following compounds has a hydrogen deficiency of 3?

A)only 1
B)only 2
C)only 3 and 4
D)only 1,3 and 4

Question 14

Which of the following molecular formulae corresponds to a compound with a hydrogen deficiency of 1?

A)C₅H₈N₂
B)C₅H₁₁N
C)C₆H₁₁N
D)C₅H₁₃NO₂

Question 15

What is the index of hydrogen deficiency of a compound with a molecular formula of C₅H₉Br?

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

Question 16

Which of the following compounds does not have a hydrogen deficiency of 5?

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

Question 17

What is the hybridization of carbon atoms labeled i - iii in the following structure?

A)i = sp; ii = sp; iii = sp
B)i = sp²; ii = p; iii = sp²
C)i = sp²; ii = sp; iii = sp²
D)i = sp²; ii = sp²; iii = sp²

Question 18

Which of the following molecular formulae corresponds to a compound with a hydrogen deficiency of 2?

A)C₅H₈O₂
B)C₅H₁₀O
C)C₆H₁₅N
D)C₅H₁₀Br₂

Question 19

Which of the following does not correspond to a molecular formula of a neutral compound?

A)C₅H₅Br
B)C₅H₇Cl₂
C)C₅H₅Br₃
D)C₅H₈Cl₄

Question 20

What is the index of hydrogen deficiency of a compound with a molecular formula of C₆H₇Cl?

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

Question 21

What is the name of the following compound?

A)vinylcyclohexane
B)allylcyclohexane
C)methylenecyclohexane
D)propargylcyclohexane

Question 22

How many constitutional isomeric alkenes are there with the formula C₆H₁₂?

A)9
B)11
C)12
D)13

Question 23

Which is the correct assignment of the names of the following groups?

A)1 = methylene; 2 = vinyl; 3 = phenyl
B)1 = vinyl; 2 = propargyl; 3 = benzyl
C)1 = allyl; 2 = vinyl; 3 = benzyl
D)1 = vinyl; 2 = allyl; 3 = phenyl

Question 24

What is the IUPAC name of the following compound?

A)(E)-3-methyl-3-pentene
B)(Z)-3-methyl-3-pentene
C)(E)-3-methyl-2-pentene
D)(Z)-3-methyl-2-pentene

Question 25

Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system used in assigning E and Z configurations of carbon-carbon double bonds?

A)"-CH(CH₃)₂"
B)"-CH₂OCH₃"
C)"-CH₂CH₃"
D)"-CH₂Br"

Question 26

What is the IUPAC name of the following compound?

A)1,3-dimethylhexene
B)2,4-dimethyl-2-hexene
C)2,4-dimethyl-1-hexene
D)3,5-dimethyl-4-hexene

Question 27

What is the IUPAC name of the following compound?

A)(E)-3-methyl-4-hexene
B)(Z)-3-methyl-4-hexene
C)(E)-4-methyl-2-hexene
D)(Z)-4-methyl-2-hexene

Question 28

What is the IUPAC name of the following compound?

A)1,3-dimethylcyclopentene
B)1,4-dimethylcyclopentene
C)2,4-dimethylcyclopentene
D)1,3-dimethyl-5-cyclopentene

Question 29

What is the IUPAC name of the following compound?

A)2-methyl-4-vinyl-2-pentene
B)3,5-dimethyl-1,4-hexadiene
C)2,4-dimethyl-3,5-hexadiene
D)1,1,3-trimethyl-1,4-pentadiene

Question 30

What is the IUPAC name of the following compound?

A)bicyclo[5.4.3]-2-octene
B)bicyclo[5.4.3]-3-octene
C)bicyclo[3.2.1]-2-octene
D)2,6-methyleno-1-cyclooctene

Question 31

Which of the following does not correspond to a molecular formula of a neutral compound?

A)C₄H₈BrNO
B)C₅H₉ClN₂O
C)C₇H₁₄BrO₃
D)C₈H₁₄ClN

Question 32

Which is the correct assignment of the common names of the following compounds?

A)1 = ethylene; 2 = isobutylene; 3 = isoprene
B)1 = acetylene; 2 = isoprene; 3 = isobutylene
C)1 = ethylene; 2 = isoprene; 3 = isobutylene
D)1 = acetylene; 2 = isobutylene; 3 = isoprene

Question 33

Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system used in assigning E and Z configurations of carbon-carbon double bonds?

A)"-COOH"
B)"-Cl"
C)"-CH₂OH"
D)"-CH₃"

Question 34

What is the name of the following compound?

A)cis-4-methyl-1-allylcyclohexane
B)cis-4-allyl-1-methylcyclohexane
C)trans-4-allyl-1-methylcyclohexane
D)cis-4-methyl-1-vinylcyclohexane

Question 35

How many alkenes have the formula C₅H₁₀?

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

Question 36

What is the IUPAC name of the following compound?

A)bicyclo[6.2]oct-2-ene
B)bicyclo[4.4.4]oct-2-ene
C)bicyclo[2.2.2]-2-octene
D)bicyclo[2.2]-2-octene

Question 37

Which is the correct assignment of the names of the following groups?

A)1 = vinyl; 2 = benzyl; 3 = allyl
B)1 = allyl; 2 = phenyl; 3 = vinyl
C)1 = methylene; 2 = phenyl; 3 = vinyl
D)1 = methylene; 2 = benzyl; 3 = allyl

Question 38

What is the IUPAC name of the following compound?

A)(Z)-3-ethyl-5-methyl-1,4-heptadiene
B)(E)-3-ethyl-5-methyl-1,4-heptadiene
C)(E)-3-methyl-5-vinyl-3-heptene
D)(Z)-1,3-diethyl-1-methyl-1,4-pentadiene

Question 39

What is the IUPAC name of the following compound?

A)2-methylenepentane
B)2-methyl-1-pentene
C)2-vinylpentane
D)2-propyl-1-propene

Question 40

What is the IUPAC name of the following compound?

A)1,2-dimethylcyclohexene
B)2,3-dimethyl-1-cyclohexene
C)1,2-dimethyl-2-cyclohexene
D)1,6-dimethylcyclohexene

Question 41

How many isomers of 1,6-heptadiene exist?

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

Question 42

The following molecular formula could represent an alkene.
C₂₇H₅₆

Question 43

How many isomers of 2,4-heptadiene exist?

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

Question 44

In the calculation of the index of hydrogen deficiency, when the elements of Group 6 are found in a formula no correction to the number of hydrogen atoms is needed.

Question 45

(3E)-3,7-dimethyl-1,3,6-octatriene can be represented by either of the following two formulas.

Question 46

Which of the following is a terpene?

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

Question 47

The presence of both rings and pi bonds contribute to the index of hydrogen deficiency in a compound.

Question 48

In the carbon-carbon bond of an alkene, a $\pi$ bond is considerably weaker than a $\sigma$ bond.

Question 49

Which of the following is not a terpene?

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

Question 50

The following compound contains a carbon-carbon double bond with Z stereochemistry.

Question 51

Consider the following two structures. The structure on the left represents the more stable form of this compound.

Question 52

Which of the following compounds is most reactive (least stable)?
a.(Z)-cycloheptene
b.(E)-cycloheptene
c.(Z)-cyclooctene
d.(E)-cyclooctene

Question 53

How many isomers of 1,3-heptadiene exist?

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

Question 54

What types of units make up terpenes?

A)isoprene
B)propene
C)vitamin A
D)pentadiene

Question 55

Which of the following is not true regarding alkenes?

A)Alkenes are non polar.
B)Alkenes burn in air to give H₂O and CO₂.
C)Alkenes are highly miscible with water.
D)The strongest intermolecular force between alkene molecules is the van der Waals interaction.

Question 56

The structure for 2,3-dimethyl-2-pentene is shown below.

Question 57

What is the smallest trans cycloalkene that is stable at room temperature?

A)(E)-cyclohexene
B)(E)-cycloheptene
C)(E)-cyclooctene
D)(E)-cyclodecene

Question 58

The following compound contains an allyl group.

Question 59

The following could be named as either trans-2-methylhex-3-ene or (Z)-2-methylhex-3-ene .

Question 60

How many isomers of 1,3,5-heptatriene exist?

A)1
B)2
C)4
D)8

Question 61

What is the value of the index of hydrogen deficiency of a molecule with the formula C₈H₁₉N?

Question 62

What is the IUPAC name of the following compound?

Question 63

What is the IUPAC name of the following compound?

Question 64

What is the IUPAC name of the following compound?

Question 65

What is the value of the index of hydrogen deficiency of aspartame, shown below?

Question 66

What is the IUPAC name of the following compound?

Question 67

What is the IUPAC name of the following compound?

Question 68

What is the IUPAC name of the following compound?

Question 69

What is the value of the index of hydrogen deficiency of a molecule with the formula C₈H₁₂?

Question 70

What is the value of the index of hydrogen deficiency of a molecule with the formula C₉H₁₀?

Question 71

Using the EZ system, the following would designated as the ____isomer.

Question 72

A compound with the following molecular formula contains two double bonds. The correct subscript for H in the formula is ________.
C₁₀H_?ClN₂O

Question 73

What is the IUPAC name of the following compound?

Question 74

Consider the compounds named below. Use the letter of the substance to answer the following questions. Some letters may be used more than once. Some questions may have more than one correct answer. In the latter case, only one letter need be given.
The compound with the lowest boiling point is represented by the letter ______.

A)propene
B)1-butene
C)2-butene
D)1-pentene
E)2-pentene

Question 75

What is the value of the index of hydrogen deficiency of Ritalin, shown below?

Question 76

What is the IUPAC name of the following compound?

Question 77

Consider the compounds named below. Use the letter of the substance to answer the following questions. Some letters may be used more than once. Some questions may have more than one correct answer. In the latter case, only one letter need be given.
A compound that can exhibit cis-trans isomerism is represented by the letter ______.

A)propene
B)1-butene
C)2-butene
D)1-pentene
E)2-pentene

Question 78

The following substance contains ______ terpene units.

Question 79

Consider the compounds named below. Use the letter of the substance to answer the following questions. Some letters may be used more than once. Some questions may have more than one correct answer. In the latter case, only one letter need be given.
A compound likely to be a liquid at room temperature is represented by the letter ______.

Question 80

What is the value of the index of hydrogen deficiency of a molecule with the formula C₇H₁₅N?