Question 1

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 2

In the mass spectrum of 3-methylhexanoic acid, predict the mass of the fragment resulting from a McLafferty rearrangement.

Accepted Answer

The answer of In the mass spectrum of 3-methylhexanoic acid,...

Question 3

In a carboxylic acid, the hybridization of the C is ________ and the OCO bond angle is ________.

Accepted Answer

A)  sp2; exactly 120° 
B)  sp2; greater than 120° 
C)  sp3; 109.5° 
D)  sp3; less than 120° 
A)  sp2; exactly 120° 
B)  sp2; greater than 120° 
C)  sp3; 109.5° 
D)  sp3; less than 120°

Question 4

Provide the IUPAC name for HO2CCH2C(CH3)2CH2CH2CO2H.

Accepted Answer

3,3-dimeth

Question 5

Name the compound shown below.

Accepted Answer

4-methylpe

Question 6

Provide the major organic product of the following reaction sequence.

Accepted Answer

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

Question 7

Using the carboxylic acid below as your only carbon source, how would you make the given amide?

Accepted Answer

@#IMG-DLM& Alternatively, the amine coul

Question 8

Provide the major organic product of the reaction shown below.

Accepted Answer

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

Question 9

Which of the following would be the preferred reagents used in the following synthesis?

Accepted Answer

A)  1. NaBH3-THF
2) H3O+ 
B)  1. Mg/ether
2) dry CO2
3) H3O+ 
C)  1. LiAlH4-THF
2) H3O+ 
D)  1. Hot KMnO4
2) H3O+ 
E)  1. LiAlH[O(CH3)3]3-THF
2) H3O+ 
A)  1. NaBH3-THF
2) H3O+ 
B)  1. Mg/ether
2) dry CO2
3) H3O+ 
C)  1. LiAlH4-THF
2) H3O+ 
D)  1. Hot KMnO4
2) H3O+ 
E)  1. LiAlH[O(CH3)3]3-THF
2) H3O+

Question 10

Provide the IUPAC name for the compound shown below.

Accepted Answer

E-2,5-dime

Question 11

An acid which could not be prepared from an organic halide by carboxylation of the Grignard reagent is ________.

Accepted Answer

A)  benzoic acid 
B)  2,2-dimethylpropanoic acid 
C)  propanoic acid 
D)  4-oxocyclohexanecarboxylic acid 
E)  2-methylbutanoic acid 
A)  benzoic acid 
B)  2,2-dimethylpropanoic acid 
C)  propanoic acid 
D)  4-oxocyclohexanecarboxylic acid 
E)  2-methylbutanoic acid

Question 12

Suggest a sequence of synthetic steps through which p-toluic acid can be prepared from toluene.

Accepted Answer

1) Br₂, FeB

Question 13

An acid which could not be prepared by the reaction of an organic halide with cyanide ion followed by acid hydrolysis of the nitrile is ________.

Accepted Answer

A)  propanoic acid 
B)  phenylacetic acid 
C)  acetic acid 
D)  (CH3)3CCO2H 
E)  CH3(CH2)14CO2H 
A)  propanoic acid 
B)  phenylacetic acid 
C)  acetic acid 
D)  (CH3)3CCO2H 
E)  CH3(CH2)14CO2H

Question 14

The common name for pentanedioic acid is ________.

Accepted Answer

A)  pimelic acid 
B)  oxalic acid 
C)  glutaric acid 
D)  succinic acid 
E)  adipic acid 
A)  pimelic acid 
B)  oxalic acid 
C)  glutaric acid 
D)  succinic acid 
E)  adipic acid

Question 15

Provide the structure of the major organic product of the reaction sequence shown.

Accepted Answer

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

Question 16

Which of the reagents listed below would work best in the following reaction?

Accepted Answer

A)  NaBH4 
B)  LiAlH4 
C)  BH3 -THF 
D)  LiAl[(OC(CH3)3]3H 
E)  none of the above 
A)  NaBH4 
B)  LiAlH4 
C)  BH3 -THF 
D)  LiAl[(OC(CH3)3]3H 
E)  none of the above

Question 17

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 18

Which of the following is the strongest acid?

Accepted Answer

A)  chloroacetic acid 
B)  dichloroacetic acid 
C)  trichloroacetic acid 
D)  acetic acid 
A)  chloroacetic acid 
B)  dichloroacetic acid 
C)  trichloroacetic acid 
D)  acetic acid

Question 19

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 20

1-Hexanol reacts with chromic acid to yield what product?

Accepted Answer

The answer of 1-Hexanol reacts with chromic acid to yield...

Exam 20: Carboxylic Acids

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

In the mass spectrum of 3-methylhexanoic acid, predict the mass of the fragment resulting from a McLafferty rearrangement.

In a carboxylic acid, the hybridization of the C is ________ and the OCO bond angle is ________.

Provide the IUPAC name for HO2CCH2C(CH3)2CH2CH2CO2H.

Name the compound shown below.

Provide the major organic product of the following reaction sequence.

Using the carboxylic acid below as your only carbon source, how would you make the given amide?

Provide the major organic product of the reaction shown below.

Which of the following would be the preferred reagents used in the following synthesis?

Provide the IUPAC name for the compound shown below.

An acid which could not be prepared from an organic halide by carboxylation of the Grignard reagent is ________.

Suggest a sequence of synthetic steps through which p-toluic acid can be prepared from toluene.

An acid which could not be prepared by the reaction of an organic halide with cyanide ion followed by acid hydrolysis of the nitrile is ________.

The common name for pentanedioic acid is ________.

Provide the structure of the major organic product of the reaction sequence shown.

Which of the reagents listed below would work best in the following reaction?

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

Which of the following is the strongest acid?

Which of the following is the strongest acid?

1-Hexanol reacts with chromic acid to yield what product?

Structure and Bonding

Acids and Bases; Functional Groups

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides; Nucleophilic Substitution

Structure and Synthesis of Alkenes; Elimination

Reactions of Alkenes

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

In a carboxylic acid, the hybridization of the C is and the OCO bond angle is .

Provide the IUPAC name for HO₂CCH₂C(CH₃)₂CH₂CH₂CO₂H.

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