Question 1

Draw all major resonance contributors of the species below.

Accepted Answer

The answer of Draw all major resonance contributors of the...

Question 2

How could the following compound be synthesized using a Diels-Alder reaction?

Accepted Answer

The answer of How could the following compound be synthesized...

Question 3

Provide the structure of the major organic product in the following reaction.

Accepted Answer

@#IMG-DLM&_TB1830_00

Question 4

Identify the resonance hybrid.

Accepted Answer

A)    
B)    
C)    
D)    
E) A, B, and C. 
A)    
B)    
C)    
D)    
E) A, B, and C.

Question 5

Which of the following is the most stable diene?

Accepted Answer

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

Question 6

Classify cyclopheptatrienyl cation as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.

Accepted Answer

The answer of Classify cyclopheptatrienyl cation as aromatic, antiaromatic, or...

Question 7

Which of the following dienes is the most reactive in a Diels-Alder reaction?

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 product from 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

Which of the following is aromatic?

Accepted Answer

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

Question 10

Which of the following ions is most acidic?

Accepted Answer

A) C6H5NH3+ 
B) C6H5CH2NH3+ 
C) (CH3)2CHNH3+ 
D) CH3CH2NH3+ 
E) CH3NH3+ 
A) C6H5NH3+ 
B) C6H5CH2NH3+ 
C) (CH3)2CHNH3+ 
D) CH3CH2NH3+ 
E) CH3NH3+

Question 11

Which of the following is an allylic cation?

Accepted Answer

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

Question 12

Why is phenol a stronger acid than cyclohexanol?

Accepted Answer

The anion of phenol is stabili

Question 13

Provide the structure of the major organic product in the following reaction.

Accepted Answer

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

Question 14

Which of the following numbered hydrogens is most easily abstracted by heterolytic cleavage? Explain.

Accepted Answer

Hydrogen #3 is most easily abs

Question 15

Which species is represented by the following distribution of p electrons in the molecular energy diagram?

Accepted Answer

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

Question 16

Give the major organic product(s)for the reaction.

Accepted Answer

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

Question 17

Which of the following statements concerning resonance contributors and resonance hybrids is not correct?

Accepted Answer

A) The fewer nearly equivalent resonance contributors are in the structure, the greater the resonance energy. 
B) A resonance hybrid is more stable than the predicted stability of any of its resonance contributors. 
C) The greater the number of relatively stable resonance contributors, the greater the resonance energy. 
D) The greater the predicted stability of a resonance contributor, the more it contributes to the resonance hybrid. 
E) none of the above 
A) The fewer nearly equivalent resonance contributors are in the structure, the greater the resonance energy. 
B) A resonance hybrid is more stable than the predicted stability of any of its resonance contributors. 
C) The greater the number of relatively stable resonance contributors, the greater the resonance energy. 
D) The greater the predicted stability of a resonance contributor, the more it contributes to the resonance hybrid. 
E) none of the above

Question 18

Rank the following dienes in order of increasing stability: trans-1,3-pentadiene, cis-1,3-pentadiene, 1,4-pentadiene, and 1,2-pentadiene.

Accepted Answer

1,2-pentadiene < 1,4

Question 19

The delocalized π system in benzene is formed by a cyclic overlap of 6 ________ orbitals.

Accepted Answer

A) s 
B) p 
C) sp 
D) sp2 
E) sp3 
A) s 
B) p 
C) sp 
D) sp2 
E) sp3

Question 20

Consider the hydrogenation reaction of each compound listed and rank the compounds in order of increasing ΔH° of this reaction. The most negative ΔH° should be listed first.
cis-2-pentene, 2,3-pentadiene, and trans-1,3-pentadiene

Accepted Answer

2,3-pentadiene < tra

Exam 8: Electron Delocalization, Resonance, and Aromaticity More About Molecular Orbital Theory

Draw all major resonance contributors of the species below.

How could the following compound be synthesized using a Diels-Alder reaction?

Provide the structure of the major organic product in the following reaction.

Identify the resonance hybrid.

Which of the following is the most stable diene?

Classify cyclopheptatrienyl cation as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.

Which of the following dienes is the most reactive in a Diels-Alder reaction?

What is the product from the following reaction?

Which of the following is aromatic?

Which of the following ions is most acidic?

Which of the following is an allylic cation?

Why is phenol a stronger acid than cyclohexanol?

Provide the structure of the major organic product in the following reaction.

Which of the following numbered hydrogens is most easily abstracted by heterolytic cleavage? Explain.

Which species is represented by the following distribution of p electrons in the molecular energy diagram?

Give the major organic product(s)for the reaction.

Which of the following statements concerning resonance contributors and resonance hybrids is not correct?

Rank the following dienes in order of increasing stability: trans-1,3-pentadiene, cis-1,3-pentadiene, 1,4-pentadiene, and 1,2-pentadiene.

The delocalized π system in benzene is formed by a cyclic overlap of 6 ________ orbitals.

Consider the hydrogenation reaction of each compound listed and rank the compounds in order of increasing ΔH° of this reaction. The most negative ΔH° should be listed first. cis-2-pentene, 2,3-pentadiene, and trans-1,3-pentadiene

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

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

Reactions of Benzene and Substituted Benzenes

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