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

Question 1

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-CH₂CH₂-Cl

Answer 1

Question 2

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

Answer 2

Question 3

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

Answer 3

Question 4

Match each definition to one of the terms below.

The energy needed by reactants to reach the transition state.

A)transition state
B)endergonic reaction
C)activation energy
D)Gibbs free energy change
E)exergonic reaction
F)reaction intermediate

Question 5

Match each definition to one of the terms below.

A species that lies at an energy maximum during an individual step in a reaction.

A)transition state
B)endergonic reaction
C)activation energy
D)Gibbs free energy change
E)exergonic reaction
F)reaction intermediate

Question 6

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

Question 7

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

Question 8

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 9

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

Question 10

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 11

Instructions: In the reaction below:
a)Label the nucleophile (Nu) and the electrophile (E).
b)Draw arrows on the structures showing electron flow in the reaction.
Label and indicate flow:

Question 12

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

Question 13

Match each definition to one of the terms below.

A reaction that involves a species with an unpaired electron.

A)polarization
B)addition reaction
C)radical reaction
D)electrophile
E)polar reaction
F)substitution
G)nucleophile
H)elimination reaction

Question 14

Instructions: Use the reaction energy diagram below to answer the following question(s).
The products are found at _____ on the diagram.

Question 15

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 16

Match each definition to one of the terms below.

Another term used for a Lewis acid.

A)polarization
B)addition reaction
C)radical reaction
D)electrophile
E)polar reaction
F)substitution
G)nucleophile
H)elimination reaction

Question 17

Instructions: Use the reaction energy diagram below to answer the following question(s).
The free-energy change for the reaction is indicated at _____ on the diagram.

Question 18

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 19

Instructions: Use the reaction energy diagram below to answer the following question(s).
The transition state is found at _____ on the diagram.

Question 20

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

Question 21

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 22

Name this compound.

Question 23

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 24

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

Question 25

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

Question 26

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 27

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

Question 28

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 29

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 30

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

Question 31

Instructions: Use the reaction energy diagram below to answer the following question(s).
The reactants are found at _____ on the diagram.

Question 32

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 33

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

Question 34

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

Question 35

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

Question 36

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 37

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 38

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 39

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 40

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