Question 1

Provide the major organic product of the reaction shown below.

Accepted Answer

The answer of Provide the major organic product of the...

Question 2

What two alkenes, which contain only one double bond, yield exclusively propanoic acid upon oxidation with hot concentrated KMnO4?

Accepted Answer

Question 3

Draw a Fischer projection of the product which results when (R)-2-bromobutane is treated with the following sequence of reagents: 1. CN-, 2. H3O+, and 3. CH2N2.

Accepted Answer

Question 4

Which sequence of steps below describes the best synthesis of 5-oxohexanoic acid starting with 1-methylcyclopentan-1-ol?

Accepted Answer

A)  1. Conc. KMnO4 2. Dry gaseous HBr
3) mg/ether
4) CO2 
B)  1. H2SO4 and heat 2. Conc. KMnO4 
C)  1. Conc. KMnO4 2. CH3MgBr/ ether
 3. H3O+ 
D)  1. H2SO4 and heat 2. O3
3) (CH3)2S
4) PCC 
E)  1. H2SO4 and heat 2. Conc. KMnO4
3) LiAlH4
4) H3O+ 
A)  1. Conc. KMnO4 2. Dry gaseous HBr
3) mg/ether
4) CO2 
B)  1. H2SO4 and heat 2. Conc. KMnO4 
C)  1. Conc. KMnO4 2. CH3MgBr/ ether
 3. H3O+ 
D)  1. H2SO4 and heat 2. O3
3) (CH3)2S
4) PCC 
E)  1. H2SO4 and heat 2. Conc. KMnO4
3) LiAlH4
4) H3O+

Question 5

Which of the following is the strongest acid?

Accepted Answer

A)  acetic acid 
B)  chloroacetic acid 
C)  bromoacetic acid 
D)  fluoroacetic acid 
A)  acetic acid 
B)  chloroacetic acid 
C)  bromoacetic acid 
D)  fluoroacetic acid

Question 6

Provide the major organic product of the reaction shown below.

Accepted Answer

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Question 7

Where would one expect to find the 1H NMR signal for the carboxyl group's hydrogen in propanoic acid?

Accepted Answer

A)  δ 4.1 - 5.6 ppm 
B)  δ 10 - 13 ppm 
C)  δ 8 - 9 ppm 
D)  δ 6.1 - 7.8 ppm 
E)  δ 9.5 - 10 ppm 
A)  δ 4.1 - 5.6 ppm 
B)  δ 10 - 13 ppm 
C)  δ 8 - 9 ppm 
D)  δ 6.1 - 7.8 ppm 
E)  δ 9.5 - 10 ppm

Question 8

In the propanoate ion,

Accepted Answer

A)  both the carbon-oxygen bonds are the same length. 
B)  the carbon-oxygen double bond is shorter. 
C)  the carbon-oxygen double bond is longer. 
D)  one of the oxygen atoms bears a -1 charge. 
E)  the carbon atom bears a -1 charge. 
A)  both the carbon-oxygen bonds are the same length. 
B)  the carbon-oxygen double bond is shorter. 
C)  the carbon-oxygen double bond is longer. 
D)  one of the oxygen atoms bears a -1 charge. 
E)  the carbon atom bears a -1 charge.

Question 9

Which of the following statements is true?

Accepted Answer

A)  At two pH units above the pKa, the carboxylate ion concentration exceeds the concentration of the carboxylic acid by a 100 to 1 ratio. 
B)  At two pH units above the pKa, the carboxylate ion concentration exceeds the concentration of the carboxylic acid by a 2 to 1 ratio. 
C)  At two pH units below the pKa, the carboxylate ion concentration exceeds the concentration of the carboxylic acid by a 2 to 1 ratio. 
D)  At two pH units below the pKa, the carboxylate ion concentration exceeds the concentration of the carboxylic acid by a 10 to 1 ratio. 
E)  At two pH units below the pKa the carboxylate ion concentration is equal to the carboxylic acid concentration. 
A)  At two pH units above the pKa, the carboxylate ion concentration exceeds the concentration of the carboxylic acid by a 100 to 1 ratio. 
B)  At two pH units above the pKa, the carboxylate ion concentration exceeds the concentration of the carboxylic acid by a 2 to 1 ratio. 
C)  At two pH units below the pKa, the carboxylate ion concentration exceeds the concentration of the carboxylic acid by a 2 to 1 ratio. 
D)  At two pH units below the pKa, the carboxylate ion concentration exceeds the concentration of the carboxylic acid by a 10 to 1 ratio. 
E)  At two pH units below the pKa the carboxylate ion concentration is equal to the carboxylic acid concentration.

Question 10

What compound is produced when (CH3)2CHCH2Br is subjected to the following sequence of steps? 1. Mg, Et2O 2. CO2

Accepted Answer

A)  2-methylpropanoic acid 
B)  3-methylpropanoic acid 
C)  2-methylbutanoic acid 
D)  3-methylbutanoic acid 
E)  2-methylhexanoic acid 
A)  2-methylpropanoic acid 
B)  3-methylpropanoic acid 
C)  2-methylbutanoic acid 
D)  3-methylbutanoic acid 
E)  2-methylhexanoic acid

Question 11

Provide the structure of trans-1,3-cyclohexanedicarboxylic acid.

Accepted Answer

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Question 12

2-Phenylethanol yields what acid upon treatment with cold chromic acid?

Accepted Answer

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Question 13

Suggest a sequence of synthetic steps through which phenylacetic acid can be prepared from toluene via phenylacetonitrile.

Accepted Answer

1. Br₂, hν

Question 14

Provide the major organic product of the reaction shown below.

Accepted Answer

The answer of Provide the major organic product of the...

Question 15

Why are the OH groups of carboxylic acids more acidic than alcohols?

Accepted Answer

A)  resonance stabilization of the carboxylate ion 
B)  inductive electron donating by the carbonyl oxygen 
C)  reduced hydrogen bonding capacity 
D)  because they have lower pKa values 
E)  None of the above - carboxylic acids are not more acidic than alcohols. 
A)  resonance stabilization of the carboxylate ion 
B)  inductive electron donating by the carbonyl oxygen 
C)  reduced hydrogen bonding capacity 
D)  because they have lower pKa values 
E)  None of the above - carboxylic acids are not more acidic than alcohols.

Question 16

What alkyllithium would react with acetic acid to form 2-butanone?

Accepted Answer

A)  methyllithium 
B)  vinyllithium 
C)  ethyllithium 
D)  propyllithium 
E)  phenyllithium 
A)  methyllithium 
B)  vinyllithium 
C)  ethyllithium 
D)  propyllithium 
E)  phenyllithium

Question 17

Mark all the sequences of reactions that convert a carboxylic acid to an aldehyde. (More than one answer is possible.)

Accepted Answer

A)  1) CH2N2 2) DIBAL 3) H3O+ 
B)  1) NaBH4 2) H3O+ 3) PCC 
C)  1) SOCl2 2) LiAl(Ot-Bu)3H 
D)  1) LiAlH4 2) Ag(NH3)2OH 
A)  1) CH2N2 2) DIBAL 3) H3O+ 
B)  1) NaBH4 2) H3O+ 3) PCC 
C)  1) SOCl2 2) LiAl(Ot-Bu)3H 
D)  1) LiAlH4 2) Ag(NH3)2OH

Question 18

Provide the structure of the major organic compound which results when cyclopentanecarboxylic acid is treated with thionyl chloride and the resulting product is treated with LiAlH[OC(CH3)3]3.

Accepted Answer

Question 19

Provide the structure of 3-nitrophthalic acid.

Accepted Answer

The answer of Provide the structure of 3-nitrophthalic acid....

Question 20

Provide the major organic product of the following reaction.

Accepted Answer

The answer of Provide the major organic product of the...

Exam 20: Carboxylic Acids

Provide the major organic product of the reaction shown below.

What two alkenes, which contain only one double bond, yield exclusively propanoic acid upon oxidation with hot concentrated KMnO4?

Draw a Fischer projection of the product which results when (R)-2-bromobutane is treated with the following sequence of reagents: 1. CN-, 2. H3O+, and 3. CH2N2.

Which sequence of steps below describes the best synthesis of 5-oxohexanoic acid starting with 1-methylcyclopentan-1-ol?

Which of the following is the strongest acid?

Provide the major organic product of the reaction shown below.

Where would one expect to find the 1H NMR signal for the carboxyl group's hydrogen in propanoic acid?

In the propanoate ion,

Which of the following statements is true?

What compound is produced when (CH3)2CHCH2Br is subjected to the following sequence of steps? 1. Mg, Et2O 2. CO2

Provide the structure of trans-1,3-cyclohexanedicarboxylic acid.

2-Phenylethanol yields what acid upon treatment with cold chromic acid?

Suggest a sequence of synthetic steps through which phenylacetic acid can be prepared from toluene via phenylacetonitrile.

Provide the major organic product of the reaction shown below.

Why are the OH groups of carboxylic acids more acidic than alcohols?

What alkyllithium would react with acetic acid to form 2-butanone?

Mark all the sequences of reactions that convert a carboxylic acid to an aldehyde. (More than one answer is possible.)

Provide the structure of the major organic compound which results when cyclopentanecarboxylic acid is treated with thionyl chloride and the resulting product is treated with LiAlH[OC(CH3)3]3.

Provide the structure of 3-nitrophthalic acid.

Provide the major organic product of the following reaction.

Introduction and Review

Structure and Properties of Organic Molecules

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides: Nucleophilic Substitution and Elimination

Structure and Synthesis of Alkenes

Reactions of Alkenes

Alkynes

Structure and Synthesis of Alcohols

Reactions of Alcohols

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Ethers, Epoxides, and Thioethers

Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

Aromatic Compounds

Reactions of Aromatic Compounds

Ketones and Aldehydes

Amines

Carboxylic Acid Derivatives

Condensations and Alpha Substitutions of Carboxyl Compounds

Carbohydrates and Nucleic Acids

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

What two alkenes, which contain only one double bond, yield exclusively propanoic acid upon oxidation with hot concentrated KMnO₄?

Draw a Fischer projection of the product which results when (R)-2-bromobutane is treated with the following sequence of reagents: 1. CN^-, 2. H₃O⁺, and 3. CH₂N₂.

Where would one expect to find the ¹H NMR signal for the carboxyl group's hydrogen in propanoic acid?

What compound is produced when (CH₃)₂CHCH₂Br is subjected to the following sequence of steps? 1. Mg, Et₂O 2. CO₂

Provide the structure of the major organic compound which results when cyclopentanecarboxylic acid is treated with thionyl chloride and the resulting product is treated with LiAlH[OC(CH₃)₃]₃.