Deck 3: Alkenes and Alkynes: the Nature of Organic Reactions

Question 1

Instructions: Pent-2-ene is an example of a disubstituted alkene. Use this alkene to answer the following question(s).
Refer to instructions. Circle the isomer of pent-2-ene that is most stable.

Answer 1

Question 2

Instructions: In the reaction below:

Answer 2

Label and indicate flow:

Question 3

Instructions: Provide names for each structure below. Be sure to include the cis,trans or E,Z designations where applicable.

Answer 3

Name and designate:

Question 4

Instructions: Provide names for each structure below. Be sure to include the cis,trans or E,Z designations where applicable.

Question 5

Instructions: Consider the reaction of 2-bromo-2-methylpropane with water, shown below, to answer the following question(s).
Refer to instructions. This reaction is an example of:

A) a substitution reaction.
B) a rearrangement reaction.
C) an elimination reaction.
D) an addition reaction.

Question 6

The following group is a substituent on a molecule. What is an accepted IUPAC name for this group?
$$\mathrm { CH } _ { 2 } = \mathrm { CH } - \mathrm { CH } _ { 2 } -$$

A) propenyl
B) allyl
C) vinyl
D) propylene
E) either a or b

Question 7

Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system?

A) -NH₂
B) -NHCH₃
C) -CH₂NH₂
D) -CH₂NHCH₃

Question 8

What is the IUPAC name of the following compound?
A. (E)-3-methylpent-3-ene
B. (Z)-3-methylpent-3-ene
C. (E)-3-methylpent-2-ene
D. (Z)-3-methylpent-2-ene

Question 9

Instructions: Assign E or Z configurations to each alkene below.

Question 10

Instructions: Draw structures corresponding to each name below.

Question 11

Instructions: Draw structures corresponding to each name below.

Question 12

Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system?

A) -COOH
B) -CHO
C) -CH₂OH
D) -CH₃

Question 13

Rank each set of substituents using the Cahn-Ingold-Prelog sequence rules by numbering the highest priority substituent 1 and numbering the lowest priority substituent 4. Place the number in the blank below the substituent.

Question 14

Choose substituents X and Y (listed in order below) for the following compound so as to make a Z isomer.
A. -Br, -NHCH₃
B. -F, -CHO
C. -I, -OCH₃
D. -COOH, -CH₂NH₂
E. -Br, -COOH

Question 15

Instructions: Use the reaction energy diagram below to answer the following question(s).

Question 16

Instructions: Provide names for each structure below. Be sure to include the cis,trans or E,Z designations where applicable.

Question 17

Name this compound.

Question 18

Instructions: Match each definition to one of the terms below.

Question 19

Instructions: Pent-2-ene is an example of a disubstituted alkene. Use this alkene to answer the following question(s).
Refer to instructions. Draw the cis and trans isomers of pent-2-ene and label them.

Question 20

Instructions: Match each definition to one of the terms below.

Question 21

The structures below show the stepwise bond making and bond breaking in this reaction. Draw curved arrows to show the electron flow that has occurred in each step.

Question 22

Instructions: Identify and label the nucleophile and electrophile in each reaction below.
Identify and label:

Question 23

Instructions: Classify each structure below as a nucleophile or electrophile, and briefly explain your choice.
Classify and explain:

Question 24

Instructions: The reaction below is commonly used as a laboratory preparation of cyclohexene. Use this reaction to answer the following question(s). Refer to instructions. The forward and reverse reactions are classified, respectively, as:

A) addition, elimination
B) elimination, substitution
C) elimination, addition
D) elimination, rearrangement
E) substitution, addition

Question 25

Instructions: Match each definition to one of the terms below.

Question 26

Instructions: Identify the functional groups present in each compound below, and predict the direction of polarity in each.
Identify and predict:
mustard gas Cl-CH₂CH₂-S-CH₂CH₂-Cl

Question 27

Predict the product of the following reaction of Prostaglandin H₂ by interpreting the flow of electrons as indicated by the curved arrows.

Question 28

Instructions: Identify and label the nucleophile and electrophile in each reaction below.
Identify and label:

Question 29

Instructions: Identify the functional groups present in each compound below, and predict the direction of polarity in each.
Identify and predict:

Question 30

Which of the following is a characteristic of a polar reaction?

A) symmetrical bond making and breaking
B) one electron from each reactant forms the bond
C) involves a neutral species with an unpaired electron
D) are more common that radical reactions
E) all of these

Question 31

Instructions: In the reaction below:
Label and indicate flow:

Question 32

In an organic reaction, which of the following is most likely to function as only a nucleophile?

A) BF₃
B) (CH₃)₂CH₂NH₂
C) Fe²⁺
D) CH₃CH₂S^-
E) both a and c

Question 33

Instructions: Add curved arrows to the following reaction(s) to indicate the flow of electrons in each.
Indicate flow:

Question 34

Instructions: Assign E or Z configurations to each alkene below.

Question 35

Instructions: Match each definition to one of the terms below.

Question 36

Below are all the chemical structures and intermediates involved in a reaction. On the structures provided, show all electron flow using the arrow formalism for the complete stepwise mechanism.

Question 37

Instructions: Add curved arrows to the following reaction(s) to indicate the flow of electrons in each.
Indicate flow:

Question 38

Instructions: Classify each reaction below as a(n):

Question 39

Instructions: Consider the reaction of 2-bromo-2-methylpropane with water, shown below, to answer the following question(s). Refer to instructions. This reaction is an example of:

A) a substitution reaction.
B) a rearrangement reaction.
C) an elimination reaction.
D) an addition reaction.

Question 41

Instructions: Classify each structure below as a nucleophile or electrophile, and briefly explain your choice.
Classify and explain:

Question 42

Instructions: Draw structures corresponding to each name below.
Draw:
trans-4,4-dimethylpent-2-ene

Question 43

Name this compound.

Question 44

Instructions: Provide names for each structure below. Be sure to include the cis,trans or E,Z designations where applicable.
Name and designate::

Question 45

Instructions: Draw structures corresponding to each name below.
Draw:
(3E)-3,7-dimethylocta-1,3,6-triene

Question 46

Choose substituents X and Y (listed in order below) for the following compound so as to make a Z isomer.

A) -Br, -NHCH₃
B) -F, -CHO
C) -I, -OCH₃
D) -COOH, -CH₂NH₂
E) -Br, -COOH

Question 47

Instructions: Assign E or Z configurations to each alkene below.
Assign:

Question 48

Rank each set of substituents using the Cahn-Ingold-Prelog sequence rules by numbering the highest priority substituent 1 and numbering the lowest priority substituent 4. Place the number in the blank below the substituent.

Question 49

Instructions: Pent-2-ene is an example of a disubstituted alkene. Use this alkene to answer the following question(s). Refer to instructions. Circle the isomer of pent-2-ene that is most stable.

Question 50

Instructions: Provide names for each structure below. Be sure to include the cis,trans or E,Z designations where applicable.
Name and designate:

Question 51

Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system?

A) -NH₂
B) -NHCH₃
C) -CH₂NH₂
D) -CH₂NHCH₃

Question 52

Predict the product of the following reaction of Prostaglandin H₂ by interpreting the flow of electrons as indicated by the curved arrows.

Question 53

Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system?

A) -COOH
B) -CHO
C) -CH₂OH
D) -CH₃

Question 54

Below are all the chemical structures and intermediates involved in a reaction. On the structures provided, show all electron flow using the arrow formalism for the complete stepwise mechanism.

Question 55

Instructions: Provide names for each structure below. Be sure to include the cis,trans or E,Z designations where applicable.
Name and designate:

Question 56

What is the IUPAC name of the following compound?

A) (E)-3-methylpent-3-ene
B) (Z)-3-methylpent-3-ene
C) (E)-3-methylpent-2-ene
D) (Z)-3-methylpent-2-ene

Question 57

Instructions: Pent-2-ene is an example of a disubstituted alkene. Use this alkene to answer the following question(s). Refer to instructions. Draw the cis and trans isomers of pent-2-ene and label them.

Question 58

Instructions: Assign E or Z configurations to each alkene below.
Assign:

Question 59

The following group is a substituent on a molecule. What is an accepted IUPAC name for this group?

A) propenyl
B) allyl
C) vinyl
D) propylene
E) either a or b

Question 60

The structures below show the stepwise bond making and bond breaking in this reaction. Draw curved arrows to show the electron flow that has occurred in each step.