Deck 13: Carboxylic Acids

Question 1

Which reactions yield the same carboxylic acid?

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

Answer 1

I, III, IV

Question 2

What is the major product of the reaction between cinnamic acid and tryptamine in water?

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

Answer 2

II

Question 3

Which compounds are soluble in water?

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

Answer 3

I, II, III

Question 4

Arrange the compounds in order of increasing boiling point (lowest first).

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

Question 5

Which is the IUPAC name for the following compound?

A) 2-oxohexanoic acid
B) 5-oxohexanoic acid
C) methyl butyroxo ketone
D) 4-ketopentanoic acid

Question 6

Which compound is prepared by reaction of benzoic acid with ammonia and water?

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

Question 7

Arrange the compounds in order of increasing solubility in water (least soluble first).

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

Question 8

Which is the correct structure for Z-3-hexenedioic acid?

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

Question 9

Arrange the compounds in order of increasing boiling point (lowest first).

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

Question 10

Which structures are correctly named?

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

Question 11

Which mixtures can be separated by treatment with aqueous NaOH?

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

Question 12

Which reactions proceed nearly to completion as written?

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

Question 13

Arrange the compounds in order of increasing acidity (lowest first).

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

Question 14

Which is the IUPAC name for the following compound?

A) E-3-phenylpropenoic acid
B) Z-3-carboxy-1-phenylethene
C) E-1-phenylpropenoic acid
D) Z-benzylacrylic acid

Question 15

Arrange the compounds in order of increasing order of solubility in water (least soluble first).

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

Question 16

Which is the structure for potassium hydrogen oxalate?

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

Question 17

Arrange the compounds in order of increasing acidity (lowest first).

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

Question 18

Arrange the compounds in order of increasing acidity (lowest first).

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

Question 19

Arrange the compounds in order of increasing order of solubility in water (least soluble first).

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

Question 20

Arrange the compounds in order of increasing boiling point (lowest first).

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

Question 21

Acetophenone (methyl phenyl ketone) is the product from thermal degradation of which compound?

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

Question 22

Which conditions are best for the transformation?

A) LiAlH₄
B) NaBH₄
C) Ag(NH₃)₂OH / NH₄OH
D) Pyridine ^. Cr₃O₄

Question 23

The major product that completes the following reaction is,

Question 24

1 Mol of benzene-1,2-dicarboxylic acid reacts with 1 mol of thionyl chloride. Which product is formed?(Hint: 2 Mols of HCl and 1 mol of SO₂ are released)

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

Question 25

Which conditions are best for making the following compound?

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

Question 26

1 Mol of benzene-1,2-dicarboxylic acid reacts with 2 mols of thionyl chloride. Which product is formed?

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

Question 27

Which acid is strongest?

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

Question 28

Which compounds undergo thermal decarboxylation easily?

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

Question 29

Which acid/base salts differ in their physical properties and can, in principle, be separated?
I. enantiomeric salts (racemic acid and achiral base)
II. meso-salts (meso-acid and achiral base)
III. diastereomeric salts (racemic acid and chiral base)
IV. diastereomeric salts (chiral acid and racemic base)

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

Question 30

An ether solution containing all of the following compounds was extracted first with 1 M HCl, then with 1 M NaOH, then with ether.
Which compound is extracted into the ether layer?

A) I
B) II
C) III
D) All of the above

Question 31

The reagents that complete the following reaction are,

Question 32

Which acid is strongest?

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

Question 33

Which conditions will convert pentanoic acid to pentanoyl chloride?

A) HCl
B) NaCl
C) SOCl₂
D) LiAlH₄ followed by HCl

Question 34

Only the S-enantiomer of naproxen inhibits the COX-1 and COX-2 enzymes, the R-enantiomer is a strong liver toxin. Therefore, only enantiomerically pure naproxen is sold in US pharmacies. Unfortunately, the classic synthesis leads to a racemic mixture. Which base do you use to separate the two enantiomers by recrystallization?

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

Question 35

An ether solution containing all of the following compounds was extracted first with 1 M HCl, then with 1M NaOH. Which compound was extracted into the basic layer?

A) I
B) II
C) III
D) All of the above

Question 36

The IUPAC name of the following structure is ___________________________.

Question 37

The IUPAC name of the following structure is ___________________________.

Question 38

The following compound is prepared by Fischer esterification of which combination of reagents?

A) 1,2-dihydroxybenzene and methanol
B) salicylic acid and methanol
C) phthalic acid and methanol
D) benzoic acid and methanol

Question 39

The amino acid tryptophan undergoes enzymatic decarboxylation to tryptamine, which is a neuromodulator in mammalian brains. What is the correct structure of tryptamine?

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

Question 40

The enzyme-catalyzed decarboxylation of glutamic acids leads to gamma-amino-butyric acid (GABA), which is a common neurotransmitter in the human brain. What is the chemical structure of GABA?

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

Question 41

What is the reaction product?
(Assume that sodium borohydride is added in sufficient quantities to reduce every group that can be reduced.)

Question 42

The reagents that complete the following reaction are,

Question 43

The product of the reaction of acetic acid and thionyl chloride is acetyl chloride.

Question 44

The product of the reaction of benzoic acid and sodium hydroxide is sodium benzoate.

Question 45

The reagents/experimental conditions that complete the following reaction are:

Question 46

What is the reaction product? (Assume that lithium aluminum hydride is added in sufficient quantities to reduce every group that can be reduced.)

Question 47

The product of the reaction of hexanoic acid and sodium borohydride is hexanol.

Question 48

The product of heating 4-oxopentanoic acid is butanone and carbon dioxide.

Question 49

The reagents that complete the following reaction are,

Question 50

The order of acidity of the following carboxylic acids is,

Question 51

The reagents that complete the following reaction are,

Question 52

The order of acidity of the following carboxylic acids is,

Question 53

The name of the following compound is 2,2-dibromopropanedioic acid.

Question 54

The order of acidity of the following carboxylic acids is,

Question 55

The structure of Z-2-butendioic acid is,

Question 56

Complete the following reaction mechanism for the Fisher esterification of acetic acid.

Question 57

The major product that completes the following reaction is,

Question 58

The major product that completes the following reaction is,

Question 59

The order of boiling points for the following compounds is,