Question 1

Draw a mechanism for the formation of the product resulting from 1,4 addition of HCl to the
molecule shown here.Include all lone pairs of electrons, curved arrows, and formal charges.

Accepted Answer

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Question 2

Which of the following structures represents the basic steroid ring system?

Accepted Answer

A)   
B)   
C)   
D)   
E)    E

Question 3

Provide the structures of the diene and the dienophile that were combined in a Diels-Alder reaction to form the structure shown.

Accepted Answer

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Question 4

Draw a mechanism for the transformation shown here.Include all lone pairs of electrons, curved arrows, and formal charges.

Accepted Answer

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Question 5

S_N1 solvolysis of each of the two bromoalkenes shown gives the same mixture of two alcohols. Draw the two alcohol products and indicate which would be the major and minor isomers.

Accepted Answer

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Question 6

Draw the lettered intermediates and products in the following synthetic sequence.Indicate the correct stereochemistry as needed.

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Question 7

Identify the isoprene units in this structure.

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Question 8

Explain the difference between the two following molecules in their S_N2 reactivity with hydroxide ion.

Accepted Answer

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Question 9

Draw the structures of the diene and dienophile used to synthesize the molecule shown here using a
Diels-Alder reaction.

Accepted Answer

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Question 10

Which of these structures is a conjugated diene?

Accepted Answer

A)   I and III
B)   I, III, V
C)   II and IV
D)   II, IV, V
E)   All of these structures are conjugated dienes

Question 11

Which of these compounds can exist as cis/trans isomers?

Accepted Answer

A)   I
B)   II
C)   III
D)   IV
E)   none

Question 12

Which of these structures is isoprene?

Accepted Answer

A)   
B)   
C)   
D)   
E)

Question 13

Devise a multistep synthesis for the following transformation.You may use any organic or inorganic reagents of your choice.Include the reagents necessary for each step and the product of each step.

Accepted Answer

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Question 14

In the rearrangement of 2-butyne to 1-butyne, what causes the reaction to go to completion?

Accepted Answer

A)   the increased stability of the terminal triple bond in the product
B)   the high  pKa  of ammonia versus the methyl group in 2-butyne
C)   the decreased activation energy for conversion of the allene intermediate to 1 -butyne
D)   the much lower pKa  of the acetylenic proton in the product versus the other species
E)   the increased stability of the 1,2 -butadiene intermediate versus 2 -butyne

Question 15

Which of the following molecules could not be made using a Diels-Alder reaction?

Accepted Answer

A)   
B)   
C)   
D)   
E)

Question 16

Convert the structure shown here to a bond-line formula showing appropriate stereochemistry at
all asymmetric carbons.

Accepted Answer

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Question 17

Draw the exo product of the Diels-Alder reaction shown here.

Accepted Answer

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Question 18

Which of these alkynes will not isomerize in the presence of  NaNH2  ?

Accepted Answer

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

Question 19

Which of the following dienes could react with acrylonitrile in a Diels-Alder reaction?

Accepted Answer

A)   
B)   
C)   
D)   
E)

Question 20

Draw the structures of the diene and dienophile used to synthesize the product shown here.

Accepted Answer

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Exam 13: Dienes and the Allyl System: 2p Orbitals in Conjugation

Draw a mechanism for the formation of the product resulting from 1,4 addition of HCl to the molecule shown here.Include all lone pairs of electrons, curved arrows, and formal charges.

Which of the following structures represents the basic steroid ring system?

Provide the structures of the diene and the dienophile that were combined in a Diels-Alder reaction to form the structure shown.

Draw a mechanism for the transformation shown here.Include all lone pairs of electrons, curved arrows, and formal charges.

S_N1 solvolysis of each of the two bromoalkenes shown gives the same mixture of two alcohols. Draw the two alcohol products and indicate which would be the major and minor isomers.

Draw the lettered intermediates and products in the following synthetic sequence.Indicate the correct stereochemistry as needed.

Identify the isoprene units in this structure.

Explain the difference between the two following molecules in their S_N2 reactivity with hydroxide ion.

Draw the structures of the diene and dienophile used to synthesize the molecule shown here using a Diels-Alder reaction.

Which of these structures is a conjugated diene?

Which of these compounds can exist as cis/trans isomers?

Which of these structures is isoprene?

Devise a multistep synthesis for the following transformation.You may use any organic or inorganic reagents of your choice.Include the reagents necessary for each step and the product of each step.

In the rearrangement of 2-butyne to 1-butyne, what causes the reaction to go to completion?

Which of the following molecules could not be made using a Diels-Alder reaction?

Convert the structure shown here to a bond-line formula showing appropriate stereochemistry at all asymmetric carbons.

Draw the exo product of the Diels-Alder reaction shown here.

Which of these alkynes will not isomerize in the presence of NaNH₂ ?

Which of the following dienes could react with acrylonitrile in a Diels-Alder reaction?

Draw the structures of the diene and dienophile used to synthesize the product shown here.

Exam 13: Dienes and the Allyl System: 2p Orbitals in Conjugation

Draw a mechanism for the formation of the product resulting from 1,4 addition of HCl to the molecule shown here.Include all lone pairs of electrons, curved arrows, and formal charges.

Which of the following structures represents the basic steroid ring system?

Provide the structures of the diene and the dienophile that were combined in a Diels-Alder reaction to form the structure shown.

Draw a mechanism for the transformation shown here.Include all lone pairs of electrons, curved arrows, and formal charges.

SN1 solvolysis of each of the two bromoalkenes shown gives the same mixture of two alcohols. Draw the two alcohol products and indicate which would be the major and minor isomers.

Draw the lettered intermediates and products in the following synthetic sequence.Indicate the correct stereochemistry as needed.

Identify the isoprene units in this structure.

Explain the difference between the two following molecules in their SN2 reactivity with hydroxide ion.

Draw the structures of the diene and dienophile used to synthesize the molecule shown here using a Diels-Alder reaction.

Which of these structures is a conjugated diene?

Which of these compounds can exist as cis/trans isomers?

Which of these structures is isoprene?

Devise a multistep synthesis for the following transformation.You may use any organic or inorganic reagents of your choice.Include the reagents necessary for each step and the product of each step.

In the rearrangement of 2-butyne to 1-butyne, what causes the reaction to go to completion?

Which of the following molecules could not be made using a Diels-Alder reaction?

Convert the structure shown here to a bond-line formula showing appropriate stereochemistry at all asymmetric carbons.

Draw the exo product of the Diels-Alder reaction shown here.

Which of these alkynes will not isomerize in the presence of NaNH2 ?

Which of the following dienes could react with acrylonitrile in a Diels-Alder reaction?

Draw the structures of the diene and dienophile used to synthesize the product shown here.

S_N1 solvolysis of each of the two bromoalkenes shown gives the same mixture of two alcohols. Draw the two alcohol products and indicate which would be the major and minor isomers.

Explain the difference between the two following molecules in their S_N2 reactivity with hydroxide ion.

Which of these alkynes will not isomerize in the presence of NaNH₂ ?