Deck 6: An Overview of Organic Reactions

Question 1

Which of the following correctly compares the two elements in terms of polarizability?

A)S > O
B)F > Br
C)N > P
D)Cl > I

Answer 1

S > O

Question 2

In the following generic reaction between a halogen (X)and an alkane (R),which of the following steps would be considered a chain termination step?

Answer 2

4,5,6

Question 3

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.If this reaction under a given set of conditions has a K_eq value of 5.67,what percent conversion to the product would be expected?

A)85%
B)5.67%
C)17%
D)15%
E)nearly 100%

Answer 3

85%

Question 4

Polarizability:

A)explains a nonpolar carbon-sulfur bond participating in polar reaction.
B)indicates the magnitude of a dipole moment.
C)is larger for smaller atoms with few electrons.
D)is the electric field associated with a polar bond.
E)all of these

Question 5

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 6

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

Indicate flow:

Question 7

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 8

In the following generic reaction between a halogen (X)and an alkane (R),which of the following steps occurs slowly due to low concentration of reactants?

Question 9

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

Question 10

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 11

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

Identify and label:

Question 12

In theory,upon reaction with water in the presence of a strong acid,which of the following will produce more than one isomeric product?

A)
B)
C)
D)
E)Both b and d

Question 13

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

Classify and explain:

Question 14

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

Classify and explain:

Question 15

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

Question 16

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 17

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

Indicate flow:

Question 18

How many monochlorosubstitution products are possible for 2,3-dimethylbutane?

A)1
B)2
C)4
D)5
E)6

Question 19

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 20

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

Identify and predict:

Question 21

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

Question 22

Instructions: Use the second and third steps of the reaction of 2-bromo-2-methylpropane with water,shown below,to answer the following question(s).

Refer to instructions.Label the nucleophile,Nu,and the electrophile,E⁺,in the blanks provided under the structures.

Question 23

Match each definition to one of the terms below.

Question 24

If the yield for the following reaction is 76%,calculate K_eq and predict the sign of DG ^$\circ$
.

Question 25

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 26

Instructions: In the reaction below:


Label and indicate flow:

Question 27

Consider the following reaction:

a)Assuming that the first step is the slow step, draw and label a qualitative energy diagram for the reaction.
b) If the second step of the reaction were the slow step, briefly explain how the values of , and DG° would change.

Question 28

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

Question 29

Instructions: Use the first step of the reaction of 2-bromo-2-methylpropane with water,shown below,to answer the following question(s).

Refer to instructions.Species B is:

A)a carbocation
B)a radical
C)a carbanion
D)a free radical

Question 30

Predict the two alcohol addition products obtained by reaction of the following alkene with aqueous acid.

Question 31

Instructions: Use the second and third steps of the reaction of 2-bromo-2-methylpropane with water,shown below,to answer the following question(s).

Refer to instructions.Draw arrows on the structures above showing electron flow in steps two and three of this reaction.

Question 32

Instructions: Use the first step of the reaction of 2-bromo-2-methylpropane with water,shown below,to answer the following question(s).

Refer to instructions.Add curved arrows to indicate electron flow in the first step.