Deck 12: Organic Acids and Bases

Question 1

The salt of propanoic acid and the sodium ion would be named as sodium propanoate.

Answer 1

True

Question 2

Serotonin is classified as a tryptamine.

Answer 2

True

Question 3

In decarboxylation reactions, the carboxylic acid group produces carbon dioxide.

Answer 3

True

Question 4

The following represents the general structure of a thioester.

Question 5

When phenol dissolves in water, it functions as

A)a weak base
B)a weak acid
C)a neutral compound

Question 6

The structure of isoleucine is The zwitterion form of the amino acid isoleucine is

Question 7

The following compound contains a thioester bond.

Question 8

The following illustrates an amine acting as hydrogen bond donor with water.

Question 9

Only amino acids can form zwitterions.

Question 10

One of the necessary components for fatty acid synthesis is a complex of malonic acid (shown below) and CoA. The structure of this complex at physiological pH would be:

Question 11

The ketone carbonyl group in the following compound is on the α carbon atom.

Question 12

The water solubility of heptanoic acid is less than that of potassium heptanoate.

Question 13

The hexanoate ion has the formula:

Question 14

Which of the following is the molecular formula for the salt of the magnesium ion and the propanoate anion?

A)Mg(C₃H₅O₂)₂
B)Mg₂C₃H₅O₂
C)Mg(C₃H₆O₂)₂
D)MgC₃H₅O₂

Question 15

Certain amines called tryptamines, have an effect on the central nervous system and share a common structural feature.

Question 16

The amine shown below is a tertiary amine.

Question 17

Which of the following would not be soluble in water?

A)potassium nonanoate
B)sodium nonanoate
C)nonanoic acid
D)All would exhibit about the same solubility in water.

Question 18

The formula for cyclopentylamine is:

Question 19

When diethylamine ionizes in water, a product of the reaction is:

Question 20

Compounds such as morphine (an amine) are often administered to a patient as a salt because the salt is more soluble in body fluids.

Question 21

The following compounds are constitutional isomers. Which has the lowest boiling point?

A)
B)
C)
D)All boiling points are about the same.

Question 22

What is the name of the following substance?
CH₃-NH-CH₂−CH₂-CH₃

A)methylpropylamine
B)propylmethylamine
C)aminobutane
D)butanamine

Question 23

Which of the following is true of both a decarboxylation reaction and an oxidative decarboxylation reaction?

A)thiol reactant
B)production of CO₂
C)presence of coenzyme
D)molecular location of the ketone group

Question 24

Which of the following solutions is most likely to have the lowest pH?

A)0.010 M propanol
B)0.010 M propanoic acid
C)0.010 M propyl amine
D)0.010 M phenol
E)0.010 M propanethiol

Question 25

Imitrex was developed in the late 1980's and is used in the treatment of migraine. The active ingredient is shown below. The substance would be classified as a(n):

A)phenethylamine
B)tryptamine
C)alkaloid
D)a and c
E)b and c

Question 26

The following compounds are constitutional isomers. Which can form hydrogen bonds with water?

A)
B)
C)
D)All can form hydrogen bonds with water.

Question 27

Which of the following classes of compounds cannot form hydrogen bonds with like molecules?

A)alcohol
B)phenol
C)thiol

Question 28

The name of the following alkylammonium salt is:

A)propylammonium butanoate
B)ethylmethylammonium butanoate
C)ethylmethylbutanoate
D)methylethylammonium propanoate

Question 29

When heated, what is the product of the decarboxylation of the following substance?

A)
B)
C)
D)This compound does not decarboxylate when heated.

Question 30

The following compounds are constitutional isomers. Which can function as only a hydrogen bond acceptor?

A)
B)
C)
D)All can only be hydrogen bond acceptors.

Question 31

The following amine is classified as:

A)primary.
B)secondary.
C)tertiary.

Question 32

What is the basis for classifying amines as primary, secondary, or tertiary?

A)the number of carbon atoms bonded directly to the nitrogen atom
B)the number of carbon atoms bonded to a carbon bearing nitrogen
C)the number of nitrogen atoms present
D)the number of hydrogen atoms present

Question 33

When propanthiol (structure shown below) ionizes in water, a product of the reaction is:
CH₃-CH₂-CH₂-SH

A)CH₃-CH₂-CH₂-SH₂⁺
B)CH₃-CH₂-CH₂-OH
C)CH₃-CH₂-CH₂-S^-
D)CH₃-CH₂-CH₂-SOH

Question 34

The active ingredient in Prozac is shown below. This compound:

A)is a hydrochloride salt.
B)contains the conjugate acid of an amine.
C)was formed by the reaction of an amine and HCl.
D)all of the above

Question 35

Which of the following solutions is most likely to have the highest pH?

A)0.010 M propanol
B)0.010 M propanoic acid
C)0.010 M propyl amine
D)0.010 M phenol
E)0.010 M propanethiol

Question 36

The formula for the organic product of the following reaction is:

A)
B)
C)
D)

Question 37

Which of the following classes of amines can act as both a hydrogen bond acceptor and a hydrogen bond donor when dissolved in water?

A)primary
B)secondary
C)tertiary
D)both primary and secondary
E)primary, secondary and tertiary

Question 38

Which of the following compounds would be the most likely to undergo decarboxylation when simply heated?

A)
B)
C)
D)

Question 39

The following compound undergoes oxidative decarboxylation using coenzyme A (CoA) as the thiol. Which of the following is a product of this reaction?

A)
B)
C)
D)

Question 40

In the formation of a thioester bond, the involved hydrogen atoms:

A)are transferred to FAD.
B)are transferred to NAD⁺.
C)remain with the thiol.
D)remain with the aldehyde.

Question 41

Which of the following types of compounds is a good candidate for decarboxylation?

A)carboxylic acid
B)ketone
C)b-keto carboxylic acid
D)a-keto carboxylic acid

Question 42

Consider the following nitrogen containing compounds. Fill in the blanks with the appropriate letter (A,B,C,D).
Structure___________________ contains an amino group.

Question 43

Consider the structures given below. Fill in the blanks with appropriate letter (A,B,C,D,E,F).
Structure ____________________ could be a hydrogen bond donor or acceptor in water.

Question 44

Which of the following is characteristic of the structure of tryptamines?

A)aromatic
B)alkene
C)secondary amine
D)all of the above

Question 45

Consider the structures given below. Fill in the blanks with appropriate letter (A,B,C,D,E,F).
Structure__________________ and structure _______________ could react to form ethyldimethylammonium propanoate.

Question 46

Consider the structures given below. Fill in the blanks with appropriate letter (A,B,C,D,E,F).
Structure ___________________ would exist as a negative ion at pH 9.

Question 47

Consider the following nitrogen containing compounds. Fill in the blanks with the appropriate letter (A,B,C,D).
Structure________________ would be the form present in a pH 2 solution.

Question 48

Consider the structures given below. Fill in the blanks with appropriate letter (A,B,C,D,E,F).
Structure__________________ would produce a solution near pH 7.

Question 49

Draw the structure of sodium benzoate.

Question 50

Using structural formulas, write the equation for the ionization of p-cresol (show below) in water.

Question 51

Consider the structures given below. Fill in the blanks with appropriate letter (A,B,C,D,E,F).
Structure____________________ would not be neutralized by the buffers found in the body.

Question 52

Consider the structures given below. Fill in the blanks with appropriate letter (A,B,C,D,E,F).
Structure ___________________ would exist as a positive ion at pH 4.

Question 53

Consider the structures given below. Fill in the blanks with appropriate letter (A,B,C,D,E,F).
Structure _____________________ would from a thioester bond with CoA.

Question 54

When a amine dissolves in water, the pH is

A)greater than 7.
B)less than 7.
C)neutral at about 7.

Question 55

Consider the structures given below. Fill in the blanks with appropriate letter (A,B,C,D,E,F).
Structure __________________ is a secondary amine.

Question 56

Consider the following nitrogen containing compounds. Fill in the blanks with the appropriate letter (A,B,C,D).
Structure __________________ represents a zwitterion.

Question 57

The structure of procaine, whose hydrochloride salt is the local anesthetic known as Novocain, is shown below. At physiological pH,

A)only nitrogen 1 will be protonated.
B)only nitrogen 2 will be protonated.
C)both nitrogen 1 and 2 will be protonated.
D)neither nitrogen 1 nor 2 will be protonated.

Question 58

Consider the structures given below. Fill in the blanks with appropriate letter (A,B,C,D,E,F).
Structure ____________________ would ionize in water and produce OH^- ions.

Question 59

Consider the structures given below. Fill in the blanks with appropriate letter (A,B,C,D,E,F).
Structure _________________________ would undergo oxidative decarboxylation.

Question 60

Which of the following statements about decarboxylation and oxidative decarboxylation reactions is(are) correct?

A)Decarboxylation reactions and oxidative decarboxylation reactions both require the presence of NAD⁺.
B)Decarboxylation reactions and oxidative decarboxylation reactions require the use of any type of carboxylic acid.
C)Thiols are require for decarboxylation but not for oxidative decarboxylation.
D)Decarboxylation reactions and oxidative decarboxylation reactions produce a product containing a carbonyl group.
E)All of these characterize these two types of reactions.

Question 61

Draw the structure of the products of both steps of the oxidative decarboxylation of the following substance in the presence of coenzyme A. Use CoA to represent the portion of the molecule that does not change in the reaction.

Question 62

Write the structural formula for the organic product of the decarboxylation of the following substance.