Deck 5: Alkenes: Bonding, Nomenclature, and Properties

Question 1

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

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

Answer 1

C₅H₇N₂O₂

Question 2

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

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

Answer 2

C₅H₇Cl₂

Question 3

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 3

i = sp²; ii = sp²; iii = sp³

Question 4

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 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 C₅H₉Br?

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 C₆H₁₅N?

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

Question 8

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 9

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 10

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 11

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 12

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

A) σ bonding
B) σ antibonding
C) π bonding
D) π antibonding

Question 13

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

A) σ bonding
B) σ antibonding
C) π bonding
D) π antibonding

Question 14

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

A) 90°
B) 109°
C) 120°
D) 180°

Question 15

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

A) 90°
B) 109°
C) 120°
D) 180°

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

A) σ bonding
B) σ antibonding
C) π bonding
D) π antibonding

Question 18

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

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

Question 19

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 20

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 21

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 22

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 23

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 24

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 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

How many alkenes have the formula C₅H₁₀?

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

Question 27

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

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

Question 28

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 29

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 30

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 31

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 32

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 33

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

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

Question 34

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 35

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 36

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

Question 39

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 40

What is the name of the following compound?

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

Question 41

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

Question 42

The following compound contains an allyl group. $\mathrm{BrCH}=\mathrm{CHCH}_{3}$

Question 43

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

Question 44

The following molecular formula could represent an alkene.
C₂₇H₅₆

Question 45

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 46

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 47

How many isomers of 1,3-heptadiene exist?

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

Question 48

In the carbon-carbon bond of an alkene, a π bond is considerably weaker than a σ bond.

Question 49

What types of units make up terpenes?

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

Question 50

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 51

How many isomers of 1,6-heptadiene exist?

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

Question 52

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

Question 53

Which of the following compounds is most reactive (least stable)?

A) (Z)-cycloheptene
B) (E)-cycloheptene
C) (Z)-cyclooctene
D) (E)-cyclooctene

Question 54

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

Question 55

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

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

Question 56

Which of the following is a terpene?

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

Question 57

Which of the following is not a terpene?

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

Question 58

2-methyl-2-hexene can exhibit cis/trans isomerism.

Question 59

The structure for 2,3-dimethyl-2-pentene is shown below. $\quad$$\quad$$\quad$$\mathrm{CH}_{3}$
$\quad$$\quad$$\quad$$\quad$ |
$\mathrm{CH}_{3} \mathrm{CHCHCH}=\mathrm{CH}_{2}$
$\quad$$\quad$ |
$\quad$$\mathrm{CH}_{3}$

Question 60

How many isomers of 2,4-heptadiene exist?

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

Question 61

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

Question 62

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

Question 63

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

Question 64

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

Question 65

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

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 IUPAC name of the following compound?

Question 70

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

Question 71

The following substance contains ______ terpene units.

Question 72

What is the IUPAC name of the following compound?

Question 73

What is the IUPAC name of the following compound?

Question 74

What is the IUPAC name of the following compound?

Question 75

What is the IUPAC name of the following compound?

Question 76

What is the IUPAC name of the following compound?

Question 77

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

Question 78

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

Question 79

What is the IUPAC name of the following compound?

Question 80

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