Deck 14: Functional Derivatives of Carboxylic Acids

Question 1

Which is the order of increasing boiling point of the following compounds (lowest first)?

A) IV, I, III, II
B) I, III, IV, II
C) II, I, IV, III
D) IV, III, II, I

Answer 1

II, I, IV, III

Question 2

Which is the final product of a series of reactions starting with ethyl benzoate and reacting with 1) aqueous sulfuric acid and heat, 2) thionyl chloride, and 3) ethylamine?

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

Answer 2

II

Question 3

Why are the amino acids in proteins connected by means of amide and not ester bonds?
(I) Amides are more stable than esters.
(II) Esters are more stable than amides.
(III) Amides can be easily transformed into carboxylic acids and amines.
(IV) Amides are resistant to hydrolysis in the absence of enzymes.

A) I, III
B) I, II
C) I, IV
D) II, III

Answer 3

I, IV

Question 4

Characterize the amides I and II in caffeine.

A) I is a primary amide, II is a tertiary amide
B) I is a secondary amide, II is a secondary amide
C) I is a tertiary amide, II is a secondary amide
D) I is a tertiary amide, II is a tertiary amide

Question 5

Carboxylic acids and amides have in general higher boiling points than esters and anhydrides because of which property?

A) dispersion forces
B) resonance stabilization
C) conjugated functional groups
D) hydrogen bonding

Question 6

Partial hydrolysis of phenobarbitol gives which compounds?

A) I, II
B) II, III
C) III, IV
D) I, III

Question 7

Which compounds will yield benzoic acid when hydrolyzed?
(I) benzyl ethanoate
(II) benzamide
(III) phenyl ethanoate
(IV) methyl benzoate

A) I, II
B) III, IV
C) I, III
D) II, IV

Question 8

Which is the product of the reaction of phthalic anhydride with 1 equivalent of methanol?

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

Question 9

Which reactions can be used to prepare an ester?

A) II, IV
B) I, III
C) I, II
D) III, IV

Question 10

What is the order of decreasing reactivity toward nucleophilic acyl substitution for these carboxylic acid derivatives (most reactive first)?

A) II, IV, I, III
B) III, IV, I, II
C) IV, I, II, III
D) I, II, III, IV

Question 11

Which is the correct structure for phenyl benzoate?

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

Question 12

Which are the best conditions for the following preparation?

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

Question 13

Which compounds are named correctly?

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

Question 14

Which is the common name for the following compound?

A) aspirin
B) cyclosporin
C) succinamide
D) salicylamide

Question 15

Which functional groups are correctly named?

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

Question 16

Which is the major product when 1,2-diaminoethane is heated with dimethyl oxalate?

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

Question 17

Penicillins derived from Penicillium fungi were the first available $\beta$ -lactam antibiotics, which inhibit the biosynthesis of the peptidoglycan layer of bacterial cell walls. Which detail of the structure of penicillin is the "lactam-unit"?

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

Question 18

Which is the major product of the reaction of 4-aminophenol with 1 equivalent of acetic anhydride?

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

Question 19

Which of the following compounds does not yield nicotinamide when reacted with ammonia at room temperature?

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

Question 20

The following reaction is fastest when Z is which group?

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

Question 21

The reagent that complete the following reaction is,

Question 22

Chitin is the main component of the cell walls of fungi, the exoskeletons of arthropods and insects and the radula of mollusks. Which statements are true? I) Chitin is made from an aminosugar.
II) Chitin contains amide bonds.
III) Chitin is a macromolecule
IV) Chitin is structurally related to cellulose

A) all of the above
B) I, II, and IV
C) I, II, and III
D) II, III, and IV

Question 23

The reagents that complete the following reaction are,

Question 24

The reagents that complete the following reaction are,

Question 25

Butyrolactone reacts with 2-methylpropan-1-amine in DMF (dimethylformamide). Which is the major product?

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

Question 26

Which reactions proceed at room temperature as written?

A) I, II
B) I, III
C) II, III
D) II, IV

Question 27

Butyrolactone reacts with isobutyl magnesium bromide. Which is the major product formed?

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

Question 28

The major product that completes the following reaction is,

Question 29

Which is the product from the following reaction?

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

Question 30

Which are the best conditions for the following reaction?

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

Question 31

Which is the product from the reaction of sodium benzoate and acetyl chloride?

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

Question 32

The major product that completes the following reaction is,

Question 33

What are the major products of the following reaction?

Question 34

Which are the best conditions for the following reaction?

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

Question 35

Which is the major product of the following reaction?

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

Question 36

Which is the product of the reaction of ethyl benzoate with 2 equivalents of methyl Grignard followed by aqueous acid?

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

Question 37

The starting material that completes the following reaction is,

Question 38

The IUPAC name of the following compound is ______________________________.

Question 39

The IUPAC name of the following compound is ______________________________.

Question 40

The major product that completes the following reaction is,

Question 41

The product of the reaction of 5-pentanolactam with aqueous acid and heat is 5-aminopentanoic acid.

Question 42

Sodium borohydride reduces propanamide to propanamine.

Question 43

The order of reactivity of the carboxylic acid derivatives with water is,

Question 44

Complete the following reaction

Question 45

1 Mol of 5-hydroxyheptanoic acid reacts with 1 mol of SOCl₂ and then with 1 mol of dimethylamine. What major products are formed in each step?

Question 46

What is the reaction mechanism of the basic hydrolysis of ethyl-benzoate?

Question 47

Complete the following reaction sequence.

Question 48

The product of the reaction of 4-butanolactone with ethanol and acid is butanoic acid and diethylether.

Question 49

The structure for cyclohexanecarboxylic 2,2-dimethylpropanoic anhydride is,

Question 50

Which is the major product formed?

Question 51

The proper mechanism for the reaction of acetyl chloride and water is shown below.

Question 52

Triethoxymethane reacts with an aqueous solution of sodium carbonate. What are the reaction products?

Question 53

The reagents that complete the following reaction are,

Question 54

The product of the reaction of propanamide with ethanol is ethyl propanoate.

Question 55

The order of reactivity of the carboxylic acid derivatives with ammonia is,

Question 56

The name of the following compound is 3-methylbutanoyl 2-methylbutanoate.

Question 57

The major product that completes the following reaction is

Question 58

1 Mol of 5-hydroxypentanoic acid reacts with 1 mol of SOCl₂ and then with 1 mol of dimethylamine. What major products are formed in each step?

Question 59

Lithium aluminum hydride reduces 3-oxobutanoic acid to 4-hydroxy-2-butanone.