Question 1

Which free radical would be most stable?

Accepted Answer

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

Question 2

Complete the following sequence of reactions,giving structural details of all key intermediates.

Accepted Answer

The answer of Complete the following sequence of reactions,giving structural...

Question 3

What product(s)would you expect from the following substitution reaction of 14C-labeled propene?

Accepted Answer

A)  "14CH2=CH-CH2Br alone" 
B)  "14CH2=CH-CH2Br and CH2=CH-14CH2Br in equal amounts 
C)  CH2=CH-14CH2Br alone" 
D)  "More 14CH2=CHCH2Br but a little CH2=CH-14CH2Br" 
E)  "More CH2=CH14CH2Br but a little 14CH2=CHCH2Br" 
A)  "14CH2=CH-CH2Br alone" 
B)  "14CH2=CH-CH2Br and CH2=CH-14CH2Br in equal amounts 
C)  CH2=CH-14CH2Br alone" 
D)  "More 14CH2=CHCH2Br but a little CH2=CH-14CH2Br" 
E)  "More CH2=CH14CH2Br but a little 14CH2=CHCH2Br"

Question 4

Which of the following would afford a synthesis of the following compound?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of these 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of these

Question 5

Which of the following would afford a synthesis of the following compound?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of these 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of these

Question 6

Which diene and dienophile would you choose to synthesize the following compound?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of these 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of these

Question 7

What product(s)would you expect from the following substitution reaction of 14C-labeled propene?

Accepted Answer

A)  "13CH2=CH-CH2Cl alone" 
B)  "13CH2=CH-CH2Cl and CH2=CH-13CH2Cl,in equal amounts" 
C)  "CH2=CH-13CH2Cl alone" 
D)  "more 13CH2=CHCH2Cl,but a little CH2=CH-13CH2Cl" 
E)  "more CH2=CH-13CH2Cl,but a little 13CH2=CHCH2Cl" 
A)  "13CH2=CH-CH2Cl alone" 
B)  "13CH2=CH-CH2Cl and CH2=CH-13CH2Cl,in equal amounts" 
C)  "CH2=CH-13CH2Cl alone" 
D)  "more 13CH2=CHCH2Cl,but a little CH2=CH-13CH2Cl" 
E)  "more CH2=CH-13CH2Cl,but a little 13CH2=CHCH2Cl"

Question 8

What is the product of the following Diels-Alder cycloaddition reaction:

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of these 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of these

Question 9

When the product distribution for a particular reaction reflects the relative rate at which the products are formed,the reaction is said to be under _______________ control.

Accepted Answer

The answer of When the product distribution for a particular...

Question 10

Arrange these hexadienes in order of expected increasing stability.

Accepted Answer

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

Question 11

The HOMO of the allylic cation has how many electrons in its ground state?

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
E)  0 
A)  1 
B)  2 
C)  3 
D)  4 
E)  0

Question 12

The HOMO of 1,3-pentadiene has how many electrons in its ground state?

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
E)  0 
A)  1 
B)  2 
C)  3 
D)  4 
E)  0

Question 13

Select the structure of the conjugated diene.

Accepted Answer

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

Question 14

Select the most energetically favorable UV transition for 1,3-butadiene.

Accepted Answer

A)  "n $\rightarrow$ $\sigma$*" 
B)  "n $\rightarrow$  $\pi$*" 
C)  " $\pi$2  $\rightarrow$$\pi$3*" 
D)  "$\sigma$ $\rightarrow$ $\sigma$*" 
E)  " $\pi$1  $\rightarrow$$\pi$4*" 
A)  "n $\rightarrow$ $\sigma$*" 
B)  "n $\rightarrow$  $\pi$*" 
C)  " $\pi$2  $\rightarrow$$\pi$3*" 
D)  "$\sigma$ $\rightarrow$ $\sigma$*" 
E)  " $\pi$1  $\rightarrow$$\pi$4*"

Question 15

What is an IUPAC name for this triene?

Accepted Answer

A)  (2E,4Z,6
E) -3,4,7,8-tetramethyl-2,4,6-Nonatriene 
B)  (2Z,4E,6
E) -3,4,7,8-tetramethyl-2,4,6-Nonatriene 
C)  (2E,4Z,6
E) -2,3,6,7-tetramethyl-3,5,7-Nonatriene 
D)  (2E,4Z,6
E) - 2,3,6,7-tetramethyl-3,5,7-Nonatriene 
E)  (2E,4E,6
E) -3,4,7,8-tetramethyl-2,4,6-Nonatriene 
A)  (2E,4Z,6
E) -3,4,7,8-tetramethyl-2,4,6-Nonatriene 
B)  (2Z,4E,6
E) -3,4,7,8-tetramethyl-2,4,6-Nonatriene 
C)  (2E,4Z,6
E) -2,3,6,7-tetramethyl-3,5,7-Nonatriene 
D)  (2E,4Z,6
E) - 2,3,6,7-tetramethyl-3,5,7-Nonatriene 
E)  (2E,4E,6
E) -3,4,7,8-tetramethyl-2,4,6-Nonatriene

Question 16

What is an IUPAC name for

Accepted Answer

A)  2,3-methylhept-2-en-4-yne 
B)  1,1,3-trimethylhex-3-yn-1-ene 
C)  1,1,3-trimethyl-3-hexyn-1-ene 
D)  2,3-dimethyl-2-hepten-4-yne 
E)  5,6-dimethyl-5-hepten-3-yne 
A)  2,3-methylhept-2-en-4-yne 
B)  1,1,3-trimethylhex-3-yn-1-ene 
C)  1,1,3-trimethyl-3-hexyn-1-ene 
D)  2,3-dimethyl-2-hepten-4-yne 
E)  5,6-dimethyl-5-hepten-3-yne

Question 17

Which diene and dienophile would you choose to synthesize the following compound?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of these 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of these

Question 18

Which of the following pairs of compounds could be used as the basis for a Diels-Alder synthesis of the compound shown below?

Accepted Answer

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

Question 19

Which is not a proper resonance structure for 1,3-butadiene?

Accepted Answer

A)  CH2=CH-CH=CH2 
B) 
  
C) 
  
D) 
  
E)  All are correct 
A)  CH2=CH-CH=CH2 
B) 
  
C) 
  
D) 
  
E)  All are correct

Question 20

Predict the product(s)of the following reaction:

Accepted Answer

The answer of Predict the product(s)of the following reaction: ...

Exam 13: Conjugated Unsaturated Systems

Which free radical would be most stable?

Complete the following sequence of reactions,giving structural details of all key intermediates.

What product(s)would you expect from the following substitution reaction of 14C-labeled propene?

Which of the following would afford a synthesis of the following compound?

Which of the following would afford a synthesis of the following compound?

Which diene and dienophile would you choose to synthesize the following compound?

What product(s)would you expect from the following substitution reaction of 14C-labeled propene?

What is the product of the following Diels-Alder cycloaddition reaction:

When the product distribution for a particular reaction reflects the relative rate at which the products are formed,the reaction is said to be under _______________ control.

Arrange these hexadienes in order of expected increasing stability.

The HOMO of the allylic cation has how many electrons in its ground state?

The HOMO of 1,3-pentadiene has how many electrons in its ground state?

Select the structure of the conjugated diene.

Select the most energetically favorable UV transition for 1,3-butadiene.

What is an IUPAC name for this triene?

What is an IUPAC name for

Which diene and dienophile would you choose to synthesize the following compound?

Which of the following pairs of compounds could be used as the basis for a Diels-Alder synthesis of the compound shown below?

Which is not a proper resonance structure for 1,3-butadiene?

Predict the product(s)of the following reaction:

Carbon Compounds and Chemical Bonds

Representative Carbon Compounds: Functional Groups, Intermolecular Forces, and Infrared Ir Spectroscopy

An Introduction to Organic Reactions: Acids and Bases

Alkanes: Nomenclature, Conformational Analysis, and an Introduction to Synthesis

Stereochemistry: Chiral Molecules

Ionic Reactions - Nucleophilic Substitution and Elimination Reactions of Alkyl Halides

Alkenes and Alkynes I: Properties and Synthesis, Elimination Reactions of Alkyl Halides

Alkenes and Alkynes Ii: Addition Reactions

Nuclear Magnetic Resonance and Mass Spectrometry: Tools for Structure Determination

Radical Reactions

Alcohols and Ethers

Alcohols From Carbonyl Compounds Oxidation-Reduction and Organometallic Compounds

Aromatic Compounds

Reactions of Aromatic Compounds

Aldehydes and Ketones I Nucleophilic Addition to the Carbonyl Group

Aldehydes and Ketones Ii Aldol Reactions

Carboxylic Acids and Their Derivatives Nucleophilic Addition - Elimination at the Acyl Carbon

Synthesis and Reactions of Beta-Dicarbonyl Compounds: More Chemistry of Enolate Ions

Amines

Phenols and Aryl Halides: Nucleophilic Aromatic Substitution

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

What product(s)would you expect from the following substitution reaction of ¹⁴C-labeled propene?

What product(s)would you expect from the following substitution reaction of ¹⁴C-labeled propene?