Deck 19: Carboxylic Acids

Question 1

Which of the following sets of reagents would accomplish the chemical transformation shown?

A)

B)

C)

D)

E)

Answer 1

Question 2

What would be the major organic product of the following reaction?

A)

B)

C)

D)

E)

Answer 2

Question 3

Which would be the best name of the following compound?

A) 2-bromo-3-isopropylbutenoic acid
B) (E)-2-bromo-3,4-dimethyl-2-pentenoic acid
C) (E)-2-bromo-3-methyl-2-hexenoic acid
D) (E)-2-bromo-3-methyl-2-pentenoic acid
E) (Z)-2-bromo-3-methyl-2-pentenoic acid

Answer 3

(E)-2-bromo-3,4-dimethyl-2-pentenoic acid

Question 4

What best accounts for the unusually high boiling points of carboxylic acids relative to other organic compounds of similar molecular weight?

A) The relatively large concentration of oxygen atoms.
B) The presence of intramolecular hydrogen bonding.
C) Carboxylic acids are mostly ionized and thus are mostly ionic compounds.
D) The presence of intermolecular hydrogen bonding.
E) Carboxylic acids do not have unusually high boiling points.

Question 5

What major product would result from the following reaction?

A)

B)

C)

D)

E)

Question 6

What reagent(s)is (are)needed to complete the reaction shown?

A) CH₃CH₂Br
B) KMnO₄/ ^-OH
C) CH₃CH₂MgBr
D) CH₃Li
E) CH₃COCl

Question 7

Rank the following in decreasing order of acidity (most acidic on left):

A) X > Z > Y
B) Y > X > Z
C) Z > X > Y
D) Z > Y > X
E) X > Y > Z

Question 8

Which,if any,of the reactions below would produce 2-methylpropanoic acid?

A)

B)

C)

D) All of these reactions would produce the desired product.
E) None of these reactions would produce the desired product.

Question 9

What reagent(s)would accomplish the following conversion?

A) Br₂
B) PBr₃
C) Br₂/light
D) Br₂ + cat.PBr₃
E) PBr₃ + cat.Br₂

Question 10

The reaction of propanoic acid with lithium aluminum hydride,followed by water,would result in what product?

A)

B)

C)

D)

E)

Question 11

What would the common name of the following di-acid be?

A) Malonic acid
B) Oxalic acid
C) Succinic acid
D) Adipic acid
E) Glutaric acid

Question 12

Which would be the strongest acid of the following?

A) BrCH₂CH₂CO₂H
B) ClCH₂CH₂CO₂H
C) CH₃CHClCO₂H
D) CF₃CO₂H
E) CH₃CHClCOCl

Question 13

The higher acidity of carboxylic acids compared to other functional groups is best explained by

A) hydrogen bonding.
B) electronegativity of oxygen.
C) water solubility.
D) resonance.
E) electronegativity of carbon.

Question 14

Which of the following sets of reagents would convert benzyl bromide to phenylethanoic acid?

A)

B)

C)

D)

E) both B and D

Question 15

What would be the organic product of the following reaction?

A) CH₃CH₂CO₂H + CO₂
B) 2 CH₃CO₂H
C)

D)

E) None of these are formed.

Question 16

Several 2-arylpropanoic acids are used as analgesics (painkillers).Three of these [Ibuprofen (= Advil),Naproxen (= Aleve)and Ketoprofen (= Orudis KT)] are currently available in over-the-counter form.Which of the following sets of reagents would accomplish conversion of an ethyl aromatic to a 2-arylpropanoic acid?

A)

B)

C)

D)

E) both A and B

Question 17

What would be the product of the following reaction?

A)

B)

C)

D)

E) none of these

Question 18

What reagent is needed to complete the reaction shown?

A) CH₃Cl
B) PCl₃
C) Cl₂
D) LiAlH₄
E) none of these

Question 19

What reagent(s)would accomplish the following?

A) Cl₂,light
B) Cl₂,H₂O
C) SOCl₂
D) MgCl₂
E) aqueous HCl

Question 20

What would be the name of the following?

A) Malonic acid
B) Propanoic acid
C) Oxalic acid
D) Succinic acid
E) Butanedioic acid

Question 21

Rank the following in order of decreasing acidity (more acidic > less acidic):

A) II > III > I > IV > V
B) IV > II > I > III > V
C) II > IV > I > III > V
D) V > III > I > II > IV
E) II > IV > I > V > III

Question 22

Carboxylic acids have unusually high boiling points because:

A) they are significantly heavier than organic molecules with the same molecular weight.
B) they repel each other in the gas phase.
C) they strongly attract each other in the liquid phase.
D) they are usually solids,and solids are not volatile.
E) they exist mostly as ions (RCO₂- + H⁺)and ionic materials are not volatile.

Question 23

Rank the following benzoic acids in order of decreasing acidity:

A) III > I > II
B) I > III > II
C) II > I > III
D) I > II > III
E) III > II > I

Question 24

In the carboxylic acid dimer (below),which bond(s)has a strength of about 6-8 kcal/mol?

A) Bond a
B) Bond b
C) Bond c
D) Bond d
E) Bond e

Question 25

Which of the following intermediates are not involved in the acid catalyzed esterification reaction of a carboxylic acid?

A)

B)

C)

D)

E) All of the above are intermediates.

Question 26

Which compound best fits the following spectroscopic data? ¹H NMR $\delta$ = 1.00 (t,J=7.4 Hz,3H); 1.65 (sextet,J=7.5 Hz,2H); 2.31 (t,J=7.4 Hz,2H); and 11.68 (s,1H)ppm.¹³C NMR $\delta$ = 13.4,18.5,36.3,179.6 ppm.

A)

B)

C)

D)

E) none of the above

Question 27

What is the IUPAC name of the following compound?

A) 2-hexyl-9-methyldecanoic acid
B) 2-isononyloctanoic acid
C) 1-methyl-9-carboxypentadecane
D) 2-hexyldecanoic acid
E) 14-methyl-7-carboxypentadecane