Deck 18: Derivatives of Carboxylic Acids: Acyl Compounds

Question 1

Which is the correct name for the following compound?

A) methyl 2-methylbutanoate
B) ethyl 2-methylbutanoate
C) ethyl butanoate
D) ethylmethylbutanoate
E) sec-butyl ethanoate

Answer 1

ethyl 2-methylbutanoate

Question 2

Which of these structures is a ?

A)
B)
C)
D)
E)

Answer 2

Question 3

Which of the following compounds will have the highest stretching frequency (that is, the highest wave number)?

A)
B)
C)
D)
E)

Answer 3

Question 4

Which of these compounds would have the most downfield carbonyl signal in its ¹³C NMR spectrum?

A)
B)
C)
D)
E)

Question 5

What is the proper IUPAC name for this compound?

A) (1S,4S)-bicyclo[2.2.1]heptan-2-amide
B) (1S,4R)-3-azabicyclo[2.2.1]heptan-2-one
C) (1S,4R)-bicylo[2.2.1]heptan-2-amide
D) (1S,2S)-bicyclo[2.2.1]-3-azaheptanone
E) (1S,4S)-3-azabicyclo[2.2.1]heptan-2-one

Question 6

Rank the following acyl compounds in order of increasing bond length.

A)
B)
C)
D)
E)

Question 7

Which of these carbonyl compounds has the least basic carbonyl oxygen atom?

A)
B)
C)
D)
E)

Question 8

What is the product of the following synthetic sequence?

A)
B)
C)
D)
E)

Question 9

Place the following compounds in order of increasing resonance stabilization.

A)
B)
C)
D)
E)

Question 10

What is the product of the reaction conditions shown?

A)
B)
C)
D)
E)

Question 11

Which of the following structures is (S)-3-methyl-2-oxacyclopent-4-en-1-one?

A)
B)
C)
D)
E)

Question 12

Which of the following reagents would you use to accomplish this transformation?

A) NaBH₄
B) LiAlH₄
C) DIBAL-H
D) H₂
E) H₃O⁺

Question 13

Which is the correct name for the following compound?

A) 2-methylpropanoic benzoic anhydride
B) benzoic methylpropanoate
C) benzoic 2-methylpropanoic anhydride
D) benzoic propanoic anhydride
E) benzoic isopropanoic anhydride

Question 14

List the reagents in sequence used for the following synthesis.

A)
B)
C)
D)
E)

Question 15

Which reagent would you use to accomplish the following transformation?

A) PLiAlH₄
B) LiBH₄
C) NaBH₄
D) DIBAL-H
E) Both a and b

Question 16

Which of the following structures is N -methylpropanamide?

A)
B)
C)
D)
E)

Question 17

Predict the product of the following reaction.

A)
B)
C)
D)
E)

Question 18

Which of the following compounds cannot be synthesized directly from ethanoyl chloride?

A)
B)
C)
D)
E)

Question 19

Which of the following reagents would you use to accomplish this transformation?

A) LiAlH₄
B) Me₂CuLi
C)
D) CH₃MgBr
E) H₂O

Question 20

Which of the following compounds is the major organic product of the reaction conditions shown?

A)
B)
C)
D)
E)

Question 21

Which of the following is the product of the reaction conditions shown?

A)
B)
C)
D)
E)

Question 22

Which of the following is the product of the reaction conditions shown?

A)
B)
C)
D)
E)

Question 23

Provide the correct IUPAC name for the following compound.

Question 24

Which of the following is the final product of the reaction conditions shown?

A)
B)
C)
D)
E)

Question 25

Draw the following compound: R-N-ethyl-N-methyl-3-hydroxybutanamide.

Question 26

Which of the following is the correct product of the reaction conditions shown?

A)
B)
C)
D)
E)

Question 27

What reagent would you use to accomplish the following transformation?

A) H₂/Pd
B) LiAlH₄
C) P₂O₅
D) NaCN , then H₃O+
E) None of these reagents could be used for this transformation.

Question 28

What is the product of the following sequence of reactions?

A)
B)
C)
D)
E)

Question 29

Which has more resonance stabilization, an ester or an acid chloride? Explain your answer.

Question 30

Why is acidic amide hydrolysis irreversible?

A)The amine leaving group is protonated, forming an ammonium ion.
B)The amide carbonyl is protonated.
C)The amine leaving group is deprotonated, forming an amide ion.
D)The carboxylic acid formed in the reaction is deprotonated.
E)The amine formed in the reaction is deprotonated.

Question 31

For compound A, in acid, it is the hydroxyl oxygen that is protonated to a greater extent than the
carbonyl oxygen. However, for compound B in acid, it is the carbonyl oxygen that is protonated to a greater extent
than the hydroxyl oxygen. Explain the difference in these results.

Question 32

Draw the structure of methyl 3,3-dimethylbutanoate.

Question 33

Which of the following compounds will not be transformed to a carboxylic acid on treatment with aqueous acid?

A)
B)
C)
D)
E) All these compounds can be transformed to carboxylic acids on treatment with aqueous acid.

Question 34

What conditions could be used to accomplish the following transformation?

A)
B)
C) Br₂ , then aqueous NaOH and heat
D) NaBH₄ in methanol solvent
E) both b and c

Question 35

Provide an acceptable name for the structure shown here.

Question 36

What is the final product of the reaction conditions shown?

A)
B)
C)
D)
E)

Question 37

Which of the following is the correct product of the reaction conditions shown?

A)
B)
C)
D)
E)

Question 38

Which of the following statements about amide hydrolysis is false?

A)Both acidic and basic pathways are addition-elimination reactions.
B)Under acidic conditions, the leaving group is ammonia or an amine.
C)Under basic conditions, the leaving group is an amide ion.
D)In both acidic and basic pathways, the amide's carbonyl oxygen is protonated.
E)Both acidic and basic amide hydrolysis pathways are irreversible.

Question 39

Which of the following is not a product of the hydrolysis of the compound shown?

A)
B)
C)
D)
E)

Question 40

Which of the following is an isolable intermediate in the reaction shown?

A)
B)
C)
D)
E)

Question 41

Match the compound shown to the correct NMR spectrum.

Question 42

Predict the product of the following reaction conditions.

Question 43

List the reagents required to convert benzoyl chloride to each product shown.

Question 44

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

Question 45

For the following reaction: How would each of the following affect the position of the equilibrium?

A)Running the reaction in methanol as a solvent
B)Running the reaction in a still at a temperature of 85-90 °C
C)Running the reaction in the presence of anhydrous sodium sulfate at room temperature

Question 46

Draw the structure of the compound with molecular formula C₄H₄O₃ that has the following spectra.

Question 47

Predict the major organic product of the reaction conditions shown here and draw a mechanism to
rationalize its formation.Include all necessary lone pairs, curved arrows, and nonzero formal
charges.

Question 48

Using as your only carbon source, provide syntheses of each of the following molecules.

Question 49

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

Question 50

Predict the product of the following reaction.

Question 51

Which of the compounds shown here matches this NMR spectrum?

Question 52

Predict the major organic product of the following reaction conditions and draw a mechanism to
rationalize its formation.Include all necessary lone pairs of electrons, curved arrows, and nonzero
formal charges.

Question 53

Predict the product of the reaction shown.

Question 54

Predict the product of the following reaction conditions.

Question 55

Show the product of the following reaction sequence.

Question 56

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

Question 57

Devise 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.Do not show any mechanisms.

Question 58

Provide the structures of two carboxylic acid derivatives from which the compound shown here
could be synthesized, along with the reagents you would use to convert each to the alcohol.

Question 59

Devise a multistep synthesis of the target material from the starting material shown.Show the
reagents needed for each step and the product of each step.Do not draw any mechanisms.

Question 60

Predict the product of the following reaction.

Question 61

Show the intermediates and final product in the following synthesis.

Question 62

Draw the mechanism and final product for the Baeyer-Villiger reaction of methyl cyclopentyl
ketone.

Question 63

The lactone shown can be synthesized in one step from two different precursors.Draw them both
and provide the reagents necessary to transform each of them into the lactone.

Question 64

Predict the product of the following reaction conditions and draw a mechanism to rationalize its
formation.Include all necessary lone pairs of electrons, curved arrows, and nonzero formal
charges.

Question 65

Devise 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.Do not show any mechanisms.

Question 66

Predict the product of the reaction conditions shown.

Question 67

Predict the product of the following reaction conditions and draw a mechanism to rationalize its
formation.Include all necessary lone pairs of electrons, curved arrows, and nonzero formal
charges.

Question 68

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