Question 1

Can one distinguish among the three isomeric xylenes using 13C NMR? Explain.

Accepted Answer

Yes. In the proton decoupled ¹³C

Question 2

Identify the best product for the following reaction.

Accepted Answer

A)    
B)    
C)    
D)    
E)    
A)    
B)    
C)    
D)    
E)

Question 3

What is the major product of the following reaction?

Accepted Answer

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

Question 4

What sequence of reagents can be used to make m-butylbenzoic acid from benzene?

Accepted Answer

The answer of What sequence of reagents can be used...

Question 5

Name the following structure.

Accepted Answer

A) 2-chlorobenzoic acid 
B) 3-chlorobenzoic acid 
C) 2-chlorobenzaldehyde 
D) 3-chlorobenzaldehyde 
E) 3-chloroacetophenone 
A) 2-chlorobenzoic acid 
B) 3-chlorobenzoic acid 
C) 2-chlorobenzaldehyde 
D) 3-chlorobenzaldehyde 
E) 3-chloroacetophenone

Question 6

Draw the four major resonance structures of the carbocation intermediate in the reaction of anisole with HNO3/H2SO4 to yield p-nitroanisole.

Accepted Answer

Question 7

Which of the following substrates is an electron withdrawing group overall?

Accepted Answer

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

Question 8

What is the major product of the following reaction?

Accepted Answer

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

Question 9

Bromination of benzene requires a Lewis acid catalyst while bromination of cyclohexene does not. Explain this difference in reactivity.

Accepted Answer

An alkene is a better nucleoph

Question 10

Which of the following compounds reacts most slowly during nitration?

Accepted Answer

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

Question 11

Draw the three major resonance structures of the carbocation intermediate in the reaction of acetophenone with HNO3/H2SO4 to yield o-nitroacetophenone. Circle the resonance form which is less stable than the other two.

Accepted Answer

Question 12

How many signals does one expect in the proton decoupled 13C NMR spectrum of o-xylene?

Accepted Answer

A) 8 
B) 6 
C) 4 
D) 3 
E) 2 
A) 8 
B) 6 
C) 4 
D) 3 
E) 2

Question 13

Provide a detailed, stepwise mechanism for the following reaction.

Accepted Answer

The answer of Provide a detailed, stepwise mechanism for the...

Question 14

Give the best product for the following reaction.

Accepted Answer

The answer of Give the best product for the following...

Question 15

What is the name of the following compound?

Accepted Answer

A) p-dichlorobenzene 
B) 1,4-dichlorobenzene 
C) phenyldichloride 
D) A and B 
E) B and C 
A) p-dichlorobenzene 
B) 1,4-dichlorobenzene 
C) phenyldichloride 
D) A and B 
E) B and C

Question 16

Give the product(s)for the following reaction.

Accepted Answer

The answer of Give the product(s)for the following reaction. ...

Question 17

Draw p-aminobenzoic acid.

Accepted Answer

The answer of Draw p-aminobenzoic acid....

Question 18

Which of the following substituents acts as a moderate activator and o/p director in electrophilic aromatic substitution reactions?

Accepted Answer

A) -Br 
B) -SO3H 
C) -CO2H 
D) -NHCOR 
E) -CHO 
A) -Br 
B) -SO3H 
C) -CO2H 
D) -NHCOR 
E) -CHO

Question 19

Which reagent is least likely to be used in the conversion shown?

Accepted Answer

A) Na2Cr2O7 
B) HNO3 
C) Sn 
D) NaNO2 
E) HCl 
A) Na2Cr2O7 
B) HNO3 
C) Sn 
D) NaNO2 
E) HCl

Question 20

Which of the following is most likely to be the first step in the general mechanism for electrophilic substitution reactions?

Accepted Answer

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

Exam 19: Reactions of Benzene and Substituted Benzenes

Can one distinguish among the three isomeric xylenes using 13C NMR? Explain.

Identify the best product for the following reaction.

What is the major product of the following reaction?

What sequence of reagents can be used to make m-butylbenzoic acid from benzene?

Name the following structure.

Draw the four major resonance structures of the carbocation intermediate in the reaction of anisole with HNO3/H2SO4 to yield p-nitroanisole.

Which of the following substrates is an electron withdrawing group overall?

What is the major product of the following reaction?

Bromination of benzene requires a Lewis acid catalyst while bromination of cyclohexene does not. Explain this difference in reactivity.

Which of the following compounds reacts most slowly during nitration?

Draw the three major resonance structures of the carbocation intermediate in the reaction of acetophenone with HNO3/H2SO4 to yield o-nitroacetophenone. Circle the resonance form which is less stable than the other two.

How many signals does one expect in the proton decoupled 13C NMR spectrum of o-xylene?

Provide a detailed, stepwise mechanism for the following reaction.

Give the best product for the following reaction.

What is the name of the following compound?

Give the product(s)for the following reaction.

Draw p-aminobenzoic acid.

Which of the following substituents acts as a moderate activator and o/p director in electrophilic aromatic substitution reactions?

Which reagent is least likely to be used in the conversion shown?

Which of the following is most likely to be the first step in the general mechanism for electrophilic substitution reactions?

Remembering General Chemistry: Electronic Structure and Bonding

Acids and Bases: Central to Understanding Organic Chemistry

An Introduction to Organic Compounds

Isomers: the Arrangement of Atoms in Space

Alkenes Thermodynamics and Kinetics

Reactions of Alkenes

Reactions of Alkynes Introduction to Multistep Synthesis

Electron Delocalization, Resonance, and Aromaticity More About Molecular Orbital Theory

Substitution Reactions of Alkyl Halides

Elimination Reactions of Alkyl Halides Competition Between Substitution and Elimination

Reactions of Alcohols, Ethers, Epoxides, and Sulfur-Containing Compounds

Organometallic Compounds

Reactions of Alkanes, Radicals

Mass Spectrometry, Infrared Spectroscopy, and Uvvis Spectroscopy

Nmr Spectroscopy

Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

Reactions of Aldehydes and Ketones

Reactions at the Alpha Carbon of Carbonyl Compounds

More About Amines Heterocylic Compounds

Carbohydrates

Amino Acids, Peptides, and Proteins

Catalysis

The Organic Mechanisms of the Coenzymes

The Chemistry of Metabolism

Nucleosides, Nucleotides, and Nucleic Acids

Synthetic Polymers

Pericyclic Reactions

Filters

Can one distinguish among the three isomeric xylenes using ¹³C NMR? Explain.

Draw the four major resonance structures of the carbocation intermediate in the reaction of anisole with HNO₃/H₂SO₄ to yield p-nitroanisole.

Draw the three major resonance structures of the carbocation intermediate in the reaction of acetophenone with HNO₃/H₂SO₄ to yield o-nitroacetophenone. Circle the resonance form which is less stable than the other two.

How many signals does one expect in the proton decoupled ¹³C NMR spectrum of o-xylene?