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

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Exam 1: Atoms and Molecules; Orbitals and Bonding64 Questionsadd course
Exam 2: Alkanes65 Questionsadd course
Exam 3: Alkenes and Alkynes70 Questionsadd course
Exam 4: Stereochemistry68 Questionsadd course
Exam 5: Rings60 Questionsadd course
Exam 6: Substituted Alkanes: Alkyl Halides, Alcohols, Amines, Ethers,thiols, and Thioethers68 Questionsadd course
Exam 7: Substitution Reactions: the Sn2 and Sn1 Reactions55 Questionsadd course
Exam 8: Elimination Reactions: the E1 and E2 Reactions45 Questionsadd course
Exam 9: Analytical Chemistry: Spectroscopy65 Questionsadd course
Exam 10: Electrophilic Additions to Alkenes68 Questionsadd course
Exam 11: More Additions to Bonds65 Questionsadd course
Exam 12: Radical Reactions65 Questionsadd course
Exam 13: Dienes and the Allyl System: 2p Orbitals in Conjugation68 Questionsadd course
Exam 14: Aromaticity66 Questionsadd course
Exam 15: Substitution Reactions of Aromatic Compounds68 Questionsadd course
Exam 16: Carbonyl Chemistry 1: Addition Reactions73 Questionsadd course
Exam 17: Carboxylic Acids66 Questionsadd course
Exam 18: Derivatives of Carboxylic Acids: Acyl Compounds68 Questionsadd course
Exam 19: Carbonyl Chemistry 2: Reactions at the Α Position71 Questionsadd course
Exam 20: Special Topic: Carbohydrates40 Questionsadd course
Exam 21: Special Topic: Bio-Organic Chemistry40 Questionsadd course
Exam 22: Special Topic: Amino Acids and Polyamino Acids Peptides and Proteins39 Questionsadd course
Exam 23: Special Topic: Reactions Controlled by Orbital Symmetry46 Questionsadd course
Exam 24: Special Topic: Intramolecular Reactions and Neighboring Group Participation40 Questionsadd course
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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. 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.

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Question 1
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Which of the following structures represents the basic steroid ring system?

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Question 2
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E

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

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Question 3
Correct Answer:
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Draw a mechanism for the transformation shown here.Include all lone pairs of electrons, curved arrows, and formal charges. Draw a mechanism for the transformation shown here.Include all lone pairs of electrons, curved arrows, and formal charges.

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Question 4

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. S<sub>N</sub>1 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. S<sub>N</sub>1 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.

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Question 5

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

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Question 6

Identify the isoprene units in this structure. Identify the isoprene units in this structure.

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Question 7

Explain the difference between the two following molecules in their SN2 reactivity with hydroxide ion.Explain the difference between the two following molecules in their S<sub>N</sub>2 reactivity with hydroxide ion.

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Question 8

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

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Question 9

Which of these structures is a conjugated diene? Which of these structures is a conjugated diene?

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Question 10

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

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Question 11

Which of these structures is isoprene?

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Question 12

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. 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.

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Question 13

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

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Question 14

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

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Question 15

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

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Question 16

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

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Question 17

Which of these alkynes will not isomerize in the presence of NaNH2 ? Which of these alkynes will not isomerize in the presence of NaNH<sub>2</sub> ?

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Question 18

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

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Question 19

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

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Question 20
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