Question 1

Which of the following statements is not true regarding benzoic acid acids?

Accepted Answer

A)  The neutral acid is the predominant species in aqueous solution at pH 7. 
C)  Sodium benzoate is less soluble in water than benzoic acid. 
D)  Benzoic acid is extracted out of diethyl ether by treatment with aqueous sodium bicarbonate. 
A)  The neutral acid is the predominant species in aqueous solution at pH 7. 
C)  Sodium benzoate is less soluble in water than benzoic acid. 
D)  Benzoic acid is extracted out of diethyl ether by treatment with aqueous sodium bicarbonate. C

Question 2

What is the major organic product obtained from the following reaction?

Accepted Answer

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

Question 3

Select the compound that is most suitable to complete the given reaction. ? $\mathrm{CH}_{3} \mathrm{COOH}+? \rightarrow 3 \mathrm{CH}_{3} \mathrm{COCl}+\mathrm{H}_{3} \mathrm{PO}_{4}$

Accepted Answer

A)  PCl3 
B)  SOCl2 
C)  HCl 
D)  PCl5 
A)  PCl3 
B)  SOCl2 
C)  HCl 
D)  PCl5 A

Question 4

What is the major organic product obtained from the following reaction?

Accepted Answer

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

Question 5

Which of the following has the highest boiling point?

Accepted Answer

A)  hexane 
B)  1-pentanol 
C)  pentanal 
D)  butanoic acid 
A)  hexane 
B)  1-pentanol 
C)  pentanal 
D)  butanoic acid

Question 6

What is the IUPAC name of the following compound?

Accepted Answer

A)  4-methyl-3-phenyl-3-pentenoic acid 
B)  4,4-dimethyl-3-phenyl-3-butenoic acid 
C)  3-phenyl-2-methyl-2-penten-5-oic acid 
D)  (Z)-3-methyl-2-phenyl-2-butenoic acid 
A)  4-methyl-3-phenyl-3-pentenoic acid 
B)  4,4-dimethyl-3-phenyl-3-butenoic acid 
C)  3-phenyl-2-methyl-2-penten-5-oic acid 
D)  (Z)-3-methyl-2-phenyl-2-butenoic acid

Question 7

Consider the following 1H NMR to answer the following question.   Spectrum obtained from: SDBSWeb : http://riodb01.ibase.aist.go.jp/sdbs/ (National Institute of Advanced Industrial Science and Technology, 11-07-08)
This compound is known to contain both a −C=O group and an −OH group. Based on this spectrum, this compound would be classified as aliphatic carboxylic acid.

Accepted Answer

A) True 
 B)False

Question 8

Match the structures with the most appropriate boiling points.
-141.2oC

Accepted Answer

A) CH3COOH 
B) CH3(CH2)2COOH 
C) CH3(CH2)4COOH 
D) CH3CH2COOH 
A) CH3COOH 
B) CH3(CH2)2COOH 
C) CH3(CH2)4COOH 
D) CH3CH2COOH

Question 9

Consider the following reaction.   The major organic product obtained is

Accepted Answer

A) True 
 B)False

Question 10

Ethyl propanoate (CH3CH2COOCH2CH3) can be prepared by the reaction of ethanol with ____________ acid.

Accepted Answer

Question 11

What is the major organic product obtained from the following sequence of reactions?

Accepted Answer

The answer of What is the major organic product obtained...

Question 12

Provide the correct name for the following compound which can be used to produce aspirin.

Accepted Answer

o-hydroxybenzoic aci

Question 13

What is the correct assignment of the names of the following substituted benzenes?

Accepted Answer

A)  1 = salicylic acid; 2 = benzoic acid; 3 = terephthalic acid; 4 = phthalic acid 
B)  1 = terephthalic acid; 2 = salicylic acid; 3 = benzoic acid; 4 = phthalic acid 
C)  1 = salicylic acid; 2 = terephthalic acid; 3 = phthalic acid; 4 = benzoic acid 
D)  1 = phthalic acid; 2 = benzoic acid; 3 = terephthalic acid; 4 = salicylic acid 
A)  1 = salicylic acid; 2 = benzoic acid; 3 = terephthalic acid; 4 = phthalic acid 
B)  1 = terephthalic acid; 2 = salicylic acid; 3 = benzoic acid; 4 = phthalic acid 
C)  1 = salicylic acid; 2 = terephthalic acid; 3 = phthalic acid; 4 = benzoic acid 
D)  1 = phthalic acid; 2 = benzoic acid; 3 = terephthalic acid; 4 = salicylic acid

Question 14

When CO2 is bubbled through an ether solution of benzylmagnesium bromide, and the resulting mixture is acidified, ____________ _____ is produced.

Accepted Answer

phenylacet

Question 15

What is the major organic product obtained from the following reaction?

Accepted Answer

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

Question 16

What is the major organic product obtained from the following reaction?

Accepted Answer

The answer of What is the major organic product obtained...

Question 17

What is the major organic product obtained from the following reaction?

Accepted Answer

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

Question 18

Which of the following is a reactive intermediate in the thermal decarboxylation of a 1,3-diacid?

Accepted Answer

A)  enol 
B)  carbocation 
C)  carbanion 
D)  carboxylate 
A)  enol 
B)  carbocation 
C)  carbanion 
D)  carboxylate

Question 19

Consider the data in the Table below to answer the following question:
Acidities of Substituted Benzoic and Acetic Acids
pKas at 25°C
Y−C6H4COOH
Y
Y−CH2COOH
meta
para
H
4.75
4.19
4.19
CN
2.47
3.64
3.55
OCH3
3.57
4.09
4.46
The structure of the acid with the strongest conjugate base in the table above is CH3COOH.

Accepted Answer

A) True 
 B)False

Question 20

What is the best choice of reagent(s) to perform the following transformation?

Accepted Answer

A)  CH3I, H2SO4 
B)  CH3MgBr 
C)  LiOCH3 
D)  CH2N2 
A)  CH3I, H2SO4 
B)  CH3MgBr 
C)  LiOCH3 
D)  CH2N2

Exam 17: Carboxylic Acids

Which of the following statements is not true regarding benzoic acid acids?

What is the major organic product obtained from the following reaction?

Select the compound that is most suitable to complete the given reaction. ? CH3COOH+?→3CH3COCl+H3PO4\mathrm{CH}_{3} \mathrm{COOH}+? \rightarrow 3 \mathrm{CH}_{3} \mathrm{COCl}+\mathrm{H}_{3} \mathrm{PO}_{4}CH3​COOH+?→3CH3​COCl+H3​PO4​

What is the major organic product obtained from the following reaction?

Which of the following has the highest boiling point?

What is the IUPAC name of the following compound?

Match the structures with the most appropriate boiling points. -141.2oC

Consider the following reaction. The major organic product obtained is

Ethyl propanoate (CH3CH2COOCH2CH3) can be prepared by the reaction of ethanol with ____________ acid.

What is the major organic product obtained from the following sequence of reactions?

Provide the correct name for the following compound which can be used to produce aspirin.

What is the correct assignment of the names of the following substituted benzenes?

When CO2 is bubbled through an ether solution of benzylmagnesium bromide, and the resulting mixture is acidified, ____________ _____ is produced.

What is the major organic product obtained from the following reaction?

What is the major organic product obtained from the following reaction?

What is the major organic product obtained from the following reaction?

Which of the following is a reactive intermediate in the thermal decarboxylation of a 1,3-diacid?

What is the best choice of reagent(s) to perform the following transformation?

Covalent Bonding and Shapes of Molecules

Alkanes and Cycloalkanes

Stereoisomerism and Chirality

Acids and Bases

Alkenes: Bonding, Nomenclature, and Properties

Reactions of Alkenes

Alkynes

Haloalkanes, Halogenation, and Radical Reactions

Nucleophilic Substitution and Beta-Elimination

Alcohols

Ethers, Epoxides, and Sulfides

Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Mass Spectrometry

An Introduction to Organometallic Compounds

Aldehydes and Ketones

Functional Derivatives of Carboxylic Acids

Enolate Anions and Enamines

Dienes, Conjugated Systems, and Pericyclic Reactions

Benzene and the Concept of Aromaticity

Reactions of Benzene and Its Derivatives

Amines

Catalytic Carbon-Carbon Bond Formation

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids

Organic Polymer Chemistry

Filters

Select the compound that is most suitable to complete the given reaction. ? $\mathrm{CH}_{3} \mathrm{COOH}+? \rightarrow 3 \mathrm{CH}_{3} \mathrm{COCl}+\mathrm{H}_{3} \mathrm{PO}_{4}$

Match the structures with the most appropriate boiling points. -141.2^oC

Ethyl propanoate (CH₃CH₂COOCH₂CH₃) can be prepared by the reaction of ethanol with ____________ acid.

When CO₂ is bubbled through an ether solution of benzylmagnesium bromide, and the resulting mixture is acidified, ________ _ is produced.