Deck 3: An Introduction to Organic Reactions: Acids and Bases

Question 1

Rank the bold-faced hydrogens for the following compounds from most acidic to least acidic.

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

Answer 1

III > V > IV > II > I

Question 2

Rank the bold-faced hydrogens for the following compounds from most acidic to least acidic.

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

Answer 2

II > III > V > IV > I

Question 3

What is/are the product(s)of the following acid-base mechanism?

A)

B)

C)

D)

E) None of the above

Answer 3

Question 4

Rank the bold-faced hydrogens for the following compounds from most acidic to least acidic.

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

Question 5

What is/are the product(s)of the following acid-base mechanism?

A)

B)

C)

D)

E) None of the above

Question 6

Rank the bold-faced hydrogens for the following compounds from most acidic to least acidic.

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

Question 7

Rank the bold-faced hydrogens for the following compounds from most acidic to least acidic.

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

Question 8

Rank the bold-faced hydrogens for the following compounds from most acidic to least acidic.

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

Question 9

Rank the bold-faced hydrogens for the following compounds from most acidic to least acidic.

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

Question 10

Rank the bold-faced hydrogens for the following compounds from most acidic to least acidic.

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

Question 11

Rank the bold-faced hydrogens for the following compounds from most acidic to least acidic.

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

Question 12

What is/are the product(s)of the following acid-base mechanism?

A)

B)

C)

D)

E) None of the above

Question 13

What is/are the product(s)of the following acid-base mechanism?

A)

B)

C)

D)

E) None of the above

Question 14

Rank the bold-faced hydrogens for the following compounds from most acidic to least acidic.

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

Question 15

What is/are the product(s)of the following acid-base mechanism?

A)

B)

C)

D)

E) None of the above

Question 16

Rank the bold-faced hydrogens for the following compounds from most acidic to least acidic.

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

Question 17

What is/are the product(s)of the following acid-base mechanism?

A)

B)

C)

D)

E) None of the above

Question 18

Rank the bold-faced hydrogens for the following compounds from most acidic to least acidic.

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

Question 19

What is/are the product(s)of the following acid-base mechanism?

A)

B)

C)

D)

E) None of the above

Question 20

Rank the bold-faced hydrogens for the following compounds from most acidic to least acidic.

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

Question 21

What reactants would give the following products?

A)

B)

C)

D)

E) No reaction

Question 22

What does the reaction between the following two species produce?

A)

B)

C)

D)

E) No reaction

Question 23

The process of bond-breaking where each fragment takes away one of the electrons from the bond is called ____________.

Question 24

What does the reaction between the following two species produce?

A)

B)

C)

D)

E) No reaction

Question 25

The four basic types of reactions are: ________________.

Question 26

What does the reaction between the following two species produce?

A)

B)

C)

D)

E) No reaction

Question 27

Which base would effectively deprotonate benzoic acid (PhCOOH)?

A) NaCl
B) H₂O
C) NaO₂CCH₃
D) t-BuOK
E) They would all effectively deprotonate benzoic acid.

Question 28

What is the major product for the following reaction?

A)

B)

C)

D)

E) No reaction

Question 29

What reactants would give the following products?

A)

B)

C)

D)

E) None of the above

Question 30

Which base would not effectively deprotonate benzoic acid (PhCOOH)?

A) i-PrMgBr
B) NaOH
C) NaH
D) (i-Pr)₂NLi
E) They would all effectively deprotonate benzoic acid.

Question 31

Which base would not effectively deprotonate phenol (PhOH)?

A) i-PrMgBr
B) H₂O
C) NaH
D) (i-Pr)₂NLi
E) t-BuOK

Question 32

Which of the reaction conditions could afford the following transfromation?

A)

B)

C)

D)

E) All of the above would work.

Question 33

Which base would not effectively deprotonate acetylene?

A) i-PrMgBr
B) KH
C) (CH₃O)₂CH₂Li
D) (i-Pr)₂NLi
E) t-BuOK

Question 34

Which combination of reagents is the least effective in generating sodium isopropoxide, (CH₃)₂CH₂ONa?

A) (CH₃)₂CH₂OH + CH₃Na
B) (CH₃)₂CH₂OH + NaNH₂
C) (CH₃)₂CH₂OH + NaH
D) (CH₃)₂CH₂OH + H₂C=CHNa
E) (CH₃)₂CH₂OH + CH₃CH₂ONa

Question 35

What is the major product for the following reaction?

A)

B)

C)

D)

E) No reaction

Question 36

What is the major product for the following reaction?

A)

B)

C)

D) LiD₂O
E) No Reaction

Question 37

Which base would not effectively deprotonate acetylene?

A) LiOCH₃
B) CH₃Li
C) CH₃OCH₂MgBr
D) KH
E) (CH₃)₂NLi

Question 38

Reagents that seek to react with a proton or some other electron-deficient center are called ____________.

Question 39

Addition reactions are characteristic of compounds with ______________.

Question 40

Which of the reaction conditions would not afford the following transfromation?

A) (CH₃)₂NH
B) (CH₃)₃N
C) (CH₃)₂NLi
D) More than one
E) None of the above

Question 41

Isotope labeling is an important tool in the study of reaction mechanisms.How will you selectively deuterate the specified hydrogen atom,indicated by an arrow,in the following compound? Use equations to clarify your answer and briefly explain your rationale.

Question 42

Briefly,but clearly,explain why the -OH hydrogen in acetic acid (CH₃CO₂H)is more acidic than in ethanol (C₂H₅OH).

Question 43

Write an equation to show the reaction between ethanol,C₂H₅OH and methyllithium,CH₃Li.Draw all non-bonding electrons and show electron flow with curved arrows.

Question 44

Define a protic solvent.

Question 45

Bond polarization that takes place through space and through the bonds of the molecule is called the _____________.

Question 46

You are planning to carry out a reaction between propyne,CH₃C≡CH and sodium amide,NaNH₂.You also need to choose an appropriate solvent for carrying out the reaction.Would ethanol be suitable for this purpose? Explain your rationale clearly.

Question 47

What are the two fundamental types of energy?