Deck 8: The Proton Transfer Reaction: an Introduction to Mechanisms,thermodynamics,and Charge Stability

Question 1

Which of the following compounds is most acidic?

A)I
B)II
C)III
D)IV
E)V

Answer 1

IV

Question 2

Which of the compounds is most basic?

A)I
B)II
C)III
D)IV
E)V

Answer 2

II

Question 3

Which of the following compounds is most acidic?

A)I
B)II
C)III
D)IV
E)V

Answer 3

I

Question 4

Which of the following protons has the lowest pKa?

A)H_A
B)H_B
C)H_C
D)H_D
E)H_E

Question 5

Which of the hydrogen atoms is most acidic?

A)H_A
B)H_B
C)H_C
D)H_D
E)H_E

Question 6

Which of the following charged compounds is most stable?

A)I
B)II
C)III
D)IV
E)V

Question 7

Which of the following protons has the lowest pKa?

A)H_A
B)H_B
C)H_C
D)H_D
E)H_E

Question 8

Which of the following molecules is most acidic?

A)I
B)II
C)III
D)IV
E)All have the same acidity.

Question 9

What is the conjugate base for phenol in the following acid-base reaction?

A)I
B)II
C)III
D)IV
E)V

Question 10

Which of the hydrogen atoms is most acidic?

A)H_A
B)H_B
C)H_C
D)H_D
E)H_E

Question 11

Which of the compounds is most acidic?

A)I
B)II
C)III
D)IV
E)V

Question 12

Which of the following is least basic?

A)I
B)II
C)III
D)IV
E)V

Question 13

Which is the conjugate base for cyclopentanethiol?

A)I
B)II
C)III
D)IV
E)V

Question 14

Which of the following compounds is most acidic?

A)I
B)II
C)III
D)IV
E)V

Question 15

Which of the following compounds is most acidic?

A)I
B)II
C)III
D)IV
E)V

Question 16

Which expression represents the K_eq for the following reaction?

A)I
B)II
C)III
D)IV
E)V

Question 17

What is the correct proton transfer mechanism for the following reaction?

A)I
B)II
C)III
D)IV
E)V

Question 18

Which of the following compounds is most acidic?

A)I
B)II
C)III
D)IV
E)V

Question 19

Which of the following compounds is least acidic?

A)I
B)II
C)III
D)IV
E)V

Question 20

Which of the following charged compounds is most stable?

A)I
B)II
C)III
D)IV
E)V

Question 21

Which of the following compounds is more acidic? Explain your choice.

Question 22

Draw the mechanism and supply the products for the following proton transfer reaction.Be sure your mechanism includes all mechanism arrows,lone pairs,and formal charges.Also supply a free energy diagram.On the diagram,label the transition state,ΔG^0‡,and ΔG⁰_rxn.

Question 23

Give the products of the following proton transfer reaction,and write the K_eq expression for the reaction.

Question 24

Which of the following compounds is most basic?

A)I
B)II
C)III
D)IV
E)V

Question 25

Suppose the following molecules undergo a proton transfer reaction.Draw the mechanism and give the most likely products.Be sure to include all mechanism arrows,electron pairs,and formal charges for all starting materials and products.

Question 26

Explain why Compound A is more acidic than Compound B.Use resonance structures to explain your answer.

Question 27

Which of the following resonance structures contributes most to the resonance hybrid?

A)I
B)II
C)III
D)IV
E)I and II equally contribute most to the hybrid

Question 28

Rank the following compounds from most acidic (rank of 1)to least acidic (rank of 5).

Question 29

Supply the conjugate acid for the following base.

Question 30

Give the K_eq expression for the following reaction.

Question 31

Which of the following compounds is most acidic?

A)I
B)II
C)III
D)IV
E)V

Question 32

Which side of the equilibrium is favored for the following reaction? Explain your choice.

Question 33

Supply the conjugate base for the following acid.

Question 34

Give the most likely products of the following proton transfer reaction.Be sure to use the most basic compound as the base.Then draw in missing lone pairs and give the mechanism for this proton transfer reaction.

Question 35

Explain why hydrogen atoms attached to sp₂ carbons are more acidic than hydrogen atoms attached to sp₃ carbons.

Question 36

Draw the mechanism for the following proton transfer reaction.Be sure your mechanism includes all mechanism arrows,lone pairs,and formal charges.Also,supply a free energy diagram.On the diagram,label the transition state,ΔG^0‡,and ΔG⁰_rxn.

Question 37

Which side of the equilibrium is favored for the following reaction? Explain your choice.

Question 38

Which of the following compounds is most acidic?

A)I
B)II
C)III
D)IV
E)V

Question 39

Which of the following is most acidic? Explain your choice.

Question 40

Which of the following compounds is most basic?

A)I
B)II
C)III
D)IV
E)V

Question 41

Draw all the resonance structures for the following compound,and determine which contributes most to the resonance hybrid.

Question 42

Rank the following carbocations in order of most stable to least stable.

Question 43

Rank the following carbocations in order of most stable to least stable.

Question 44

Rank the following compounds in order of most basic to least basic.

Question 45

Rank the acidity of the following compounds in order of most acidic to least acidic.

Question 46

Rank the acidity of the following compounds in order of most acidic to least acidic.

Question 47

Rank the following compounds in order of most basic to least basic.

Question 48

Rank the acidity of the following compounds in order of most acidic to least acidic.

Question 49

Rank the acidity of the following compounds in order of most acidic to least acidic.

Question 50

Which of the following compounds is most acidic? Explain your answer.

Question 51

Rank the following compounds in order of most basic to least basic.