Deck 17: Carboxylic Acids, Esters, and Amides

Question 1

What are the products of the reaction shown?

A)hexyl cyclopentanoate + water
B)cyclopentyl hexanoate + water
C)pentyl cyclopentanoate + water
D)cyclopentyl pentanoate + water

Answer 1

B

Question 2

What is the hydrolysis reaction of an ester by a base called?

A)an addition reaction
B)a Fischer esterification
C)a substitution reaction
D)a saponification

Answer 2

D

Question 3

Which statement is not true?

A)Olestra has properties similar to the triacylglycerols in fats and oils.
B)All natural and synthetic fibers are polymers.
C)Fibers like wool and silk obtained from animals are proteins, and are joined together by many ester linkages.
D)Olestra has so many ester units clustered together that they are too crowded to be hydrolyzed.

Answer 3

C

Question 4

What products are formed in the base hydrolysis of the ester shown below with NaOH?

A)ethanol and acetic acid
B)acetic acid and sodium ethoxide
C)methanol and sodium propanoate
D)sodium acetate and water
E)sodium acetate and ethanol

Question 5

Which is not a polyamide?

A)Kevlar
B)Nylon
C)Olestra
D)N, N-dimethylpropylamide
E)More than one of the compounds above is not a polyamide.

Question 6

What is the IUPAC name of the compound below?

A)heptyl propanoate
B)hexyl propanoate
C)propyl heptanoate
D)4-decanoate
E)propyl hexanoate

Question 7

What is the IUPAC name of the compound below?

A)2-methyl-2-propylpropanoic acid
B)2-methyl-2-propyl-1-propanoic acid
C)2, 2-dimethylpentanoic acid
D)2, 2-dimethyl-1-pentoic acid
E)4, 4-dimethylpentanoic acid

Question 8

Heating a carboxylic acid with a primary amine forms water along with what organic product?

A)a primary amide
B)a secondary amide
C)a tertiary amide
D)an ester

Question 9

Carboxylic acids react with bases such as NaOH to form what type of compounds?

A)alcohols
B)esters
C)carboxylate salts
D)carboxylic amides

Question 10

Which carboxylic acid is responsible for the sting of some types of ants?

A)formic acid (HCO₂H)
B)hexanoic acid (CH₃(CH₂)₄COOH)
C)acetic acid (CH₃CO₂H)
D)propanoic acid (CH₃CH₂COOH)

Question 11

What organic product is formed when a carboxylic acid reacts with an alcohol in the presence of sulfuric acid?

A)an ether
B)an ester
C)a ketone
D)an amide

Question 12

Which of the following properly describes soaps?

A)fatty acids
B)salts of carboxylic acids that have a long hydrocarbon chain
C)salts of carboxylic acids that have a short hydrocarbon chain
D)carboxylic acids

Question 13

What is the IUPAC name of the compound below?

A)N, N-dimethylpropanamide
B)N, N-dimethylethylamide
C)dimethylpropanamide
D)dimethylaminopropanamide

Question 14

What products are formed in the acid hydrolysis of the ester shown below?

A)ethanol and acetic acid
B)acetic acid and water
C)propanoic acid and ethanol
D)acetic acid and ethane
E)ethanal and ethanol

Question 15

Which statement about the labeled carbons in the compound below is true?

A)C1 is an $\alpha$ carbon and C2 is a $\beta$ carbon
B)C2 is an $\alpha$ carbon and C1 is a $\beta$ carbon
C)C3 is an $\alpha$ carbon and C2 is a $\beta$ carbon
D)C2 is an $\alpha$ carbon and C3 is a $\beta$ carbon

Question 16

Which amide has the lowest boiling point?

A)CH₃(CH₂)₅CONH₂
B)CH₃CH₂CON(CH₂CH₃)₂
C)CH₃CH₂CH₂CH₂CONHCH₂CH₃
D)All of the amides above have the same boiling point.

Question 17

What is the IUPAC name of the compound below?

A)propanamide
B)ethylamide
C)propanamine
D)N-propylamide

Question 18

What is the common name of the compound below?

A)m-bromobenzoic acid
B)3-bromoacetobenzenoic acid
C)o-bromobenzene carboxylic acid
D)3-bromo-1-acetobenzoic acid

Question 19

The reaction of a carboxylic acid (RCOOH)with an alcohol (R'OH)in the presence of an acid catalyst to form an ester (RCOOR')is called which of the following?

A)an addition reaction
B)a Fischer esterification
C)an acid-base reaction
D)a saponification

Question 20

Which compound has the highest boiling point?

A)(CH₃)₂CHCH₂CHO
B)CH₃CH₂CH₂CH₂CH₂COOH
C)(CH₃)₂CHCH₂CH₂CH₂OH
D)CH₃(CH₂)₆CH₃
E)All of the compounds above have the same boiling point.

Question 21

The compound below is named potassium 2-chloro-3-hydroxybutanoate.

Question 22

Which statement is false?

A)Aspirin is a synthetic compound; that is, it does not occur in nature.
B)The active ingredient in aspirin is acetylsalicylic acid.
C)Salicin, found in willow bark, and salicylic acid, found in meadowsweet blossoms, have structures that are similar to aspirin.
D)Aspirin is a strong acid.

Question 23

When the compound below reacts with water in the presence of HCl, ethanol and acetic acid are formed.

Question 24

When soap is mixed with water, the nonpolar hydrocarbon tails dissolve the dirt on the exterior of micelles.

Question 25

To be active, aspirin must cross a cell membrane, and to do so, it must be ionic.

Question 26

Clavulanic acid (structure shown)is a drug used in conjunction with some antibiotics to overcome certain types of antibiotic resistance. How many chirality centers are in clavulanic acid?

A)0
B)1
C)2
D)3
E)4

Question 27

Clavulanic acid (structure shown)is a drug used in conjunction with some antibiotics to overcome certain types of antibiotic resistance. How many chirality centers are in clavulanic acid?

A)0
B)1
C)2
D)3
E)4

Question 28

Animal fats and vegetable oils are composed of triacylglycerols.

Question 29

Which of these structures represents a soap?

A)CH₃CO₂^- K⁺
B)CH₃(CH₂)₁₄CO₂^- Na⁺
C)CH₃(CH₂)₁₂COOH
D)CH₃(CH₂)₇CO₂(CH₂)₇Na
E)More than one of the compounds above is a soap.

Question 30

Aspirin relieves pain and decreases inflammation because it prevents the synthesis of prostaglandins, the compounds responsible for both of these physiological responses.

Question 31

Triacylglycerols are esters formed from glycerol and three acids, each of which has a long carbon chain bonded to the carbonyl group.

Question 32

Which name is possible for a carboxylic acid?

A)1-chloropentanoic acid
B)2-pentylbutanoic acid
C)m-butylbenzoic acid
D)6, 6-dimethylhexanoic acid

Question 33

Clavulanic acid (structure shown)is a drug used in conjunction with some antibiotics to overcome certain types of antibiotic resistance. Which of these functional groups is NOT contained in clavulanic acid?

A)carboxylic acid
B) $\beta$ -lactam
C)lactone
D)ether

Question 34

The compound below can hydrogen bond to another molecule like itself.

Question 35

Treatment of an amide (RCONHR')with water in the presence of an acid catalyst (HCl)forms a carboxylic acid with the structure R'COOH, and an amine salt with the structure RNH₃⁺ Cl^-.

Question 36

Which compound is the most soluble in water?

A)(CH₃)₂CHCH₂COOCH₃
B)CH₃CH₂CH₂CH₂CH₂COOH
C)CH₃(CH₂)₆CH₃
D)CH₃CH₂CH₂CH₂CH₂COOK

Question 37

A common type of reaction for acyl compounds is substitution.

Question 38

The compound below is named potassium 2-chloro-3-hydroxybutanoate.

Question 39

Fischer esterification can be used to synthesize aspirin from salicylic acid.

Question 40

Clavulanic acid (structure shown)is a drug used in conjunction with some antibiotics to overcome certain types of antibiotic resistance. Which of these functional groups is NOT contained in clavulanic acid?

A)carboxylic acid
B) $\beta$ -lactam
C)lactone
D)ether

Question 41

The compound 3-chloro-2-hydroxybutanoic acid is an $\alpha$ -hydroxy acid.

Question 42

Nylon is an example of a condensation polymer.

Question 43

Compounds that contain both a hydroxyl group (OH)and a carboxyl group (COOH)can undergo an intramolecular esterification reaction. The lactone product shown is the result of the intramolecular esterification reaction of the indicated starting material.

Question 44

Penicillin acts as an antibiotic by reacting with an enzyme needed to synthesize the cell nucleus of a bacterium.

Question 45

The first step in the metabolism of a triacylglycerol is hydrolysis of the ester bonds to form glycerol and three fatty acids in a reaction called a simple ester hydrolysis. In the cells of the body, this reaction is catalyzed by acids.

Question 46

A lactam can be a primary amide.

Question 47

The ester below contains a propoxy group.

Question 48

Polyesters are condensation polymers.

Question 49

The two compounds below have approximately the same boiling point.

Question 50

Compounds that contain both a hydroxyl group (OH)and a carboxyl group (COOH)can undergo an intramolecular esterification reaction. The lactone product shown is the result of the intramolecular esterification reaction of the indicated starting material.

Question 51

All natural and synthetic fibers are polymers.

Question 52

The compound below is an example of a lactam.

Question 53

The compound below has the molecular formula C₉H₁₁NO, contains a benzene ring, and is a 2° amide.

Question 54

A condensation polymer is a polymer formed when monomers containing two functional groups come together with the gain of a small molecule such as water.

Question 55

The compound below has the molecular formula C₉H₁₁NO, contains a benzene ring, and is a 2° amide.

Question 56

The ester below contains a propoxy group.

Question 57

The salts of carboxylic acids are commonly used as preservatives.

Question 58

When a carboxylic acid is dissolved in water, an acid-base equilibrium occurs: the carboxylic acid donates a proton to H₂O, forming its conjugate base, a carboxylate anion, and water gains a proton, forming its conjugate acid, H₃O⁺.

Question 59

The two compounds below have approximately the same boiling point.

Question 60

The polyamide product shown is the result of the polymerization reaction between the indicated diacid and amine.

Question 61

All carbonyl compounds that contain a nitrogen atom are amides.

Question 62

The psychoactive drug benzodiazepine (structure shown)contains two amide groups.

Question 63

Carboxylic acids are capable of hydrogen bonding and often form dimers.

Question 64

(CH₃)₂CHCH₂OH has a lower boiling point than CH₃CH₂COOH.

Question 65

The IUPAC name of the compound below is _____.

Question 66

_____ is the common name of the simplest amide.

Question 67

In a propanoic acid dimer, the two propanoic acid molecules are held together by two _____.

Question 68

The name of the compound below is N-ethylpentanamide.

Question 69

The name of the compound below is N-ethylpentanamide.

Question 70

A tertiary amide contains _____ C-N bonds.

Question 71

A cyclic ester is called a(n)_____.

Question 72

Carboxylic acids, esters, and amides are three families of organic molecules that contain a carbonyl group (C=O)bonded to an element more electronegative than carbon.

Question 73

The IUPAC name of the compound below is _____.

Question 74

Carboxylic acids, esters, and amides are called _____ compounds.

Question 75

(CH₃)₂CHCHO has a lower boiling point than CH₃CH₂CH₂CH₂COOH.

Question 76

Dissolving soap in water forms spherical droplets called _____.

Question 77

The two compounds shown below are formed when N-butylacetamide is hydrolyzed with water in the presence of NaOH. and

Question 78

Tertiary (3°)amides have higher boiling points and melting points than primary (1°)and secondary (2°)amides.

Question 79

When a carboxylic acid is dissolved in water, an acid-base equilibrium occurs: the carboxylic acid donates a proton to H₂O, forming its conjugate base, a _____, and water gains a proton, forming its conjugate acid, H₃O⁺.

Question 80

When trimethylamine is heated up with propanoic acid, an amide is formed.