Deck 17: Carboxylic Acids

Question 1

Which of the following statements about carboxylic acids is/are true?

A)Carboxylic acids are Brønsted acids.
B)Carboxylic acids are Brønsted bases.
C)Carboxylic acids are Lewis acids.
D)Carboxylic acids are Lewis bases.
E)All these statements are true.

Answer 1

All these statements are true.

Question 2

Which of these carboxylic acids is most acidic?

A)
B)
C)
D)
E)

Answer 2

Question 3

Which of these carboxylic acids is in the s-cis conformation?

A)
B)
C)
D)
E) both c and d

Answer 3

Question 4

Which of these structures is 3-pentenoic acid?

A)
B)
C)
D)
E) None of these structures is 3-pentenoic acid

Question 5

Predict the major organic product of the following reaction.

A)
B)
C)
D)
E)

Question 6

Which of the following compounds corresponds to the spectrum shown here?

A)
B)
C)
D)
E)

Question 7

What is the product of the reaction shown here?

A)
B)
C)
D)
E)

Question 8

Which reagent would you use to accomplish the following transformation?

A) HCl
B) Cl₂/FeCl₃
C) SOCl₂
D) Cl₂ and heat
E) either b or c

Question 9

What reagent would you use to accomplish the following transformation?

A) O₃ , then (CH₃)₂S
B) CH₃MgBr, then H₃O⁺
C)HIO₄
D) H₃O⁺
E) KMnO₄

Question 10

Which of the following statements is true?

A) Carboxylate anions are more susceptible to nucleophilic addition than carboxylic acids.
B) Polarization in the C=O bond destabilizes a carboxylate anion.
C) The carbonyl carbon atom in a carboxylic acid reacts as a Lewis base.
D) Protonation of a carboxylic acid generally occurs faster at the hydroxyl group than at the carbonyl oxygen.
E) Removal of the hydroxyl proton in a carboxylic acid is often the fastest reaction that carboxylic acids undergo.

Question 11

Which of the following is the correct name for the compound shown here?

A) 2-methyl butanoic acid
B) 2-ethyl propanoic acid
C) (S)-2 -methyl butanoic acid
D) (R)-2 -methyl butanoic acid
E) (S)-2 -ethyl propanoic acid

Question 12

Which of the following compounds corresponds to the spectrum shown here?

A)
B)
C)
D)
E)

Question 13

What is the product of the following reaction?

A)
B)
C)
D)
E) No reaction would occur.

Question 14

Which of these structures is not a mechanistic intermediate in acid-catalyzed esterification of a carboxylic acid?

A)
B)
C)
D)
E)

Question 15

Which pair of starting materials is needed to make Pentex^TM polymer, whose structure fragment is shown below?

A)
B)
C)
D)
E)

Question 16

Place the carboxylic acids shown here in order of increasing acidity.

A) C < A < B < D
B) B < D < C < A
C) D < B < C < A
D) D < B < A < C
E) B < D < A < C

Question 17

Which of the following reagents could be used to accomplish the transformation shown here?

A) CH₂N₂
B) Methanol and trace H₂SO₄
C) CH₃Li, then H₃O⁺
D) a and b
E) a, b , and c

Question 18

Which starting material(s) is/are needed to make Kevlar^TM polymer, whose structure fragment is shown below?

A)
B)
C)
D)
E)

Question 19

Predict the product of the following reaction.

A)
B)
C)
D)
E)

Question 20

Which of the following reagents could be used to accomplish the following transformation?

A)
B)
C)
D)
E) either a or b

Question 21

What is the product of the following reaction

A)
B)
C)
D)
E)

Question 22

Explain the difference in acidity between the two acids shown here.

Question 23

Starting from benzene, devise two multistep syntheses to make the compound shown here.

Question 24

In the presence of a strong acid, one of the oxygen atoms on the carboxylic acid shown here will become protonated.Which oxygen atom is protonated and why?

Question 25

What is reagent X?

A) CH₃CH₂Br
B) NaBH₄
C) OsO4
D) ethanol
E) H₃O⁺

Question 26

What is the product of the reaction shown here?

A)
B)
C)
D)
E)

Question 27

What is the major organic product of the following reaction?

A)
B)
C)
D)
E)

Question 28

Which of the following structures will not decarboxylate when heated?

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

Question 29

The reaction shown here is accelerated by using a crown ether called 18-crown-6.Explain why the crown ether has this effect on the reaction.

Question 30

What is the product of the reaction conditions shown here?

A)
B)
C)
D)
E)

Question 31

What are the products of this reaction?

A)
B)
C)
D)
E) The reaction s stable to heating and no reaction will occur.

Question 32

What is the major organic product of this reaction?

A)
B)
C)
D)
E)

Question 33

Which of the following compounds do you expect to be unstable?

A)
B)
C)
D)
E)

Question 34

A compound with a brutto formula C₃H₄O₂ has a sharp IR band at 1690 and a broad IR band at ~3100cm^-1 . The 1H NMR spectrum contains three signals: a broad singlet and three multiplets (all doublets of doublets). What is this compound's structure?

Question 35

Provide an IUPAC name for the carboxylic acid shown here.

Question 36

Which of the following compounds could not be the starting material for the acid shown below?

A)
B)
C)
D)
E) The acid could be made from all these compounds.

Question 37

What is the major organic product of the following reaction?

A)
B)
C)
D)
E)

Question 38

Which reagent would you use to accomplish the following transformation?

A) LiAlH₄
B) CH₃Br, then H₃O⁺
C) 1 equiv. CH₃Li, then H₃O⁺
D) 2 equiv. CH₃Li, then H₃O⁺
E) CH₃OH and trace H₂SO₄

Question 39

What is the major product of the following reaction?

A)CH₄
B)C₂H₆
C)C₃H₈
D)C₄H₁₀
E)

Question 40

What is the product of the following sequence of reactions?

A)
B)
C)
D)
E)

Question 41

Draw a mechanism to rationalize the transformation shown here.

Question 42

Draw the structures of the alcohol and carboxylic acid that you would combine to produce the ester shown here.

Question 43

Isophthaloyl chloride was used as a starting material in a synthesis of the following polymer.What
was the structure of its coupling partner X?

Question 44

Draw a mechanism for the transformation shown here.Include all necessary lone pairs, curved arrows, and nonzero formal charges.

Question 45

Predict the major organic product of the following reaction conditions.

Question 46

Draw a mechanism for the following transformation.Include all necessary lone pairs, curved
arrows, and nonzero formal charges.

Question 47

What is the product of the following reaction?

Question 48

The compound shown here is the result of a decarboxylation.What is the compound that was
heated to give this product?

Question 49

Predict the product of the electrochemical oxidation of the compound shown here.

Question 50

Heating of the lactam shown below results in a linear polyamide.Draw its structure.

Question 51

Draw the structure of polyethylene terephtalate (PET), obtained by reaction below:

Question 52

What is the product of the following reaction?

Question 53

Design a multistep synthesis of the target molecule from the starting material shown.Show the
reagents needed for each step and the product of each step.You may use any organic or inorganic
reagents, but you may only add a maximum of three carbons to the molecule per step.

Question 54

Indicate how you could form the following ester using a carboxylate ion and an appropriate electrophile.

Question 55

The reaction shown here is called "iodolactonization." Five-membered rings are usually favored.
Predict the product of this reaction (no need to show stereochemistry).

Question 56

Provide a mechanism for the following transformation.Include all necessary lone pairs, curved arrows, and nonzero formal charges.

Question 57

Predict the product and draw a mechanism for the following transformation.

Question 58

What reagent can be used to accomplish the following transformation?

Question 59

Draw a mechanism for the following transformation.Include all necessary lone pairs, curved
arrows, and nonzero formal charges.

Question 60

Draw a mechanism for the following transformation.Include all necessary lone pairs, curved
arrows, and nonzero formal charges.

Question 61

Design a multistep synthesis of the target molecule from the starting material shown.Show the reagents needed for each step and the product of each step.

Question 62

Explain how soap works.

Question 63

Predict the major organic product and draw a mechanism for the following transformation.Include
all necessary lone pairs, curved arrows, and nonzero formal charges.

Question 64

Suggest a synthesis of 4-pivaloylbenzoic acid from 4-bromotoluene.

ANS:

Question 65

Provide the missing reagents and structures in the following reaction sequence.

Question 66

Design a multistep synthesis of the target molecule from the starting material shown.Show the reagents needed for each step and the product of each step.