(a) Interpretation: For the given Diels-Alder reaction, two constitutional isomers can be produced. The mechanism for the formation of each isomer is to be drawn. Concept introduction: The [ 4+2 ] cycloaddition reactions are generally known as a Diels-Alder reaction. In this reaction, a conjugated diene and a dienophile are joined via the formation of two new sigma bonds. The product is a six-membered ring. For a Diels-Alder reaction to proceed, the diene essential be able to achieve the s-cis conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Electron-donating groups attached to the diene and electron-withdrawing groups attached to the dienophile facilitates the reaction. These reactions are highly stereospecific and regioselective. Substituents that are cis to each other about the carbon-carbon double bond of the dienophile end up cis to each other in the new ring that is produced. Otherwise, the substituents end up trans to each other in the ring. Substituents attached to the terminal carbons of the diene end up cis to each other in the new ring that is produced if the double bonds of the diene are both cis or both trans. Otherwise, the substituents end up trans to each other in the ring. When the diene and dienophile are both unsymmetric, two isomeric products can be produced.

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Answer 1

Question

Chapter 24, Problem 24.49P

Interpretation Introduction

(a)

Interpretation:

For the given Diels-Alder reaction, two constitutional isomers can be produced. The mechanism for the formation of each isomer is to be drawn.

Concept introduction:

The [4+2] cycloaddition reactions are generally known as a Diels-Alder reaction. In this reaction, a conjugated diene and a dienophile are joined via the formation of two new sigma bonds. The product is a six-membered ring. For a Diels-Alder reaction to proceed, the diene essential be able to achieve the s-cis conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Electron-donating groups attached to the diene and electron-withdrawing groups attached to the dienophile facilitates the reaction. These reactions are highly stereospecific and regioselective. Substituents that are cis to each other about the carbon-carbon double bond of the dienophile end up cis to each other in the new ring that is produced. Otherwise, the substituents end up trans to each other in the ring. Substituents attached to the terminal carbons of the diene end up cis to each other in the new ring that is produced if the double bonds of the diene are both cis or both trans. Otherwise, the substituents end up trans to each other in the ring. When the diene and dienophile are both unsymmetric, two isomeric products can be produced.

Interpretation Introduction

(b)

Interpretation:

The major product among the two possible products for the given Diels-Alder reaction is to be determined.

Concept introduction:

The [4+2] cycloaddition reactions are generally known as a Diels-Alder reaction. In this reaction, a conjugated diene and a dienophile are joined via the formation of two new sigma bonds. The product is a six-membered ring. For a Diels-Alder reaction to proceed, the diene essential be able to achieve the s-cis conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Electron-donating groups attached to the diene and electron-withdrawing groups attached to the dienophile facilitates the reaction. These reactions are highly stereospecific and regioselective. Substituents that are cis to each other about the carbon-carbon double bond of the dienophile end up cis to each other in the new ring that is produced. Otherwise, the substituents end up trans to each other in the ring. Substituents attached to the terminal carbons of the diene end up cis to each other in the new ring that is produced if the double bonds of the diene are both cis or both trans. Otherwise, the substituents end up trans to each other in the ring. When the diene and dienophile are both unsymmetric, two isomeric products can be produced.

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1. Calculate the accurate monoisotopic mass (using all 1H, 12C, 14N, 160 and 35CI) for your product using the table in your lab manual. Don't include the Cl, since you should only have [M+H]*. Compare this to the value you see on the LC-MS printout. How much different are they? 2. There are four isotopic peaks for the [M+H]* ion at m/z 240, 241, 242 and 243. For one point of extra credit, explain what each of these is and why they are present. 3. There is a fragment ion at m/z 184. For one point of extra credit, identify this fragment and confirm by calculating the accurate monoisotopic mass. 4. The UV spectrum is also at the bottom of your printout. For one point of extra credit, look up the UV spectrum of bupropion on Google Images and compare to your spectrum. Do they match? Cite your source. 5. For most of you, there will be a second chromatographic peak whose m/z is 74 (to a round number). For one point of extra credit, see if you can identify this molecule as well and confirm by…

Please draw, not just describe!

can you draw each step on a piece of a paper please this is very confusing to me

Answer 2

Question

Chapter 24, Problem 24.49P

Interpretation Introduction

(a)

Interpretation:

For the given Diels-Alder reaction, two constitutional isomers can be produced. The mechanism for the formation of each isomer is to be drawn.

Concept introduction:

The [4+2] cycloaddition reactions are generally known as a Diels-Alder reaction. In this reaction, a conjugated diene and a dienophile are joined via the formation of two new sigma bonds. The product is a six-membered ring. For a Diels-Alder reaction to proceed, the diene essential be able to achieve the s-cis conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Electron-donating groups attached to the diene and electron-withdrawing groups attached to the dienophile facilitates the reaction. These reactions are highly stereospecific and regioselective. Substituents that are cis to each other about the carbon-carbon double bond of the dienophile end up cis to each other in the new ring that is produced. Otherwise, the substituents end up trans to each other in the ring. Substituents attached to the terminal carbons of the diene end up cis to each other in the new ring that is produced if the double bonds of the diene are both cis or both trans. Otherwise, the substituents end up trans to each other in the ring. When the diene and dienophile are both unsymmetric, two isomeric products can be produced.

Interpretation Introduction

(b)

Interpretation:

The major product among the two possible products for the given Diels-Alder reaction is to be determined.

Concept introduction:

The [4+2] cycloaddition reactions are generally known as a Diels-Alder reaction. In this reaction, a conjugated diene and a dienophile are joined via the formation of two new sigma bonds. The product is a six-membered ring. For a Diels-Alder reaction to proceed, the diene essential be able to achieve the s-cis conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Electron-donating groups attached to the diene and electron-withdrawing groups attached to the dienophile facilitates the reaction. These reactions are highly stereospecific and regioselective. Substituents that are cis to each other about the carbon-carbon double bond of the dienophile end up cis to each other in the new ring that is produced. Otherwise, the substituents end up trans to each other in the ring. Substituents attached to the terminal carbons of the diene end up cis to each other in the new ring that is produced if the double bonds of the diene are both cis or both trans. Otherwise, the substituents end up trans to each other in the ring. When the diene and dienophile are both unsymmetric, two isomeric products can be produced.

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Answer 3

Question

Chapter 24, Problem 24.49P

Interpretation Introduction

(a)

Interpretation:

For the given Diels-Alder reaction, two constitutional isomers can be produced. The mechanism for the formation of each isomer is to be drawn.

Concept introduction:

The [4+2] cycloaddition reactions are generally known as a Diels-Alder reaction. In this reaction, a conjugated diene and a dienophile are joined via the formation of two new sigma bonds. The product is a six-membered ring. For a Diels-Alder reaction to proceed, the diene essential be able to achieve the s-cis conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Electron-donating groups attached to the diene and electron-withdrawing groups attached to the dienophile facilitates the reaction. These reactions are highly stereospecific and regioselective. Substituents that are cis to each other about the carbon-carbon double bond of the dienophile end up cis to each other in the new ring that is produced. Otherwise, the substituents end up trans to each other in the ring. Substituents attached to the terminal carbons of the diene end up cis to each other in the new ring that is produced if the double bonds of the diene are both cis or both trans. Otherwise, the substituents end up trans to each other in the ring. When the diene and dienophile are both unsymmetric, two isomeric products can be produced.

Interpretation Introduction

(b)

Interpretation:

The major product among the two possible products for the given Diels-Alder reaction is to be determined.

Concept introduction:

The [4+2] cycloaddition reactions are generally known as a Diels-Alder reaction. In this reaction, a conjugated diene and a dienophile are joined via the formation of two new sigma bonds. The product is a six-membered ring. For a Diels-Alder reaction to proceed, the diene essential be able to achieve the s-cis conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Electron-donating groups attached to the diene and electron-withdrawing groups attached to the dienophile facilitates the reaction. These reactions are highly stereospecific and regioselective. Substituents that are cis to each other about the carbon-carbon double bond of the dienophile end up cis to each other in the new ring that is produced. Otherwise, the substituents end up trans to each other in the ring. Substituents attached to the terminal carbons of the diene end up cis to each other in the new ring that is produced if the double bonds of the diene are both cis or both trans. Otherwise, the substituents end up trans to each other in the ring. When the diene and dienophile are both unsymmetric, two isomeric products can be produced.

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Answer 4

Question

Chapter 24, Problem 24.49P

Interpretation Introduction

(a)

Interpretation:

For the given Diels-Alder reaction, two constitutional isomers can be produced. The mechanism for the formation of each isomer is to be drawn.

Concept introduction:

The [4+2] cycloaddition reactions are generally known as a Diels-Alder reaction. In this reaction, a conjugated diene and a dienophile are joined via the formation of two new sigma bonds. The product is a six-membered ring. For a Diels-Alder reaction to proceed, the diene essential be able to achieve the s-cis conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Electron-donating groups attached to the diene and electron-withdrawing groups attached to the dienophile facilitates the reaction. These reactions are highly stereospecific and regioselective. Substituents that are cis to each other about the carbon-carbon double bond of the dienophile end up cis to each other in the new ring that is produced. Otherwise, the substituents end up trans to each other in the ring. Substituents attached to the terminal carbons of the diene end up cis to each other in the new ring that is produced if the double bonds of the diene are both cis or both trans. Otherwise, the substituents end up trans to each other in the ring. When the diene and dienophile are both unsymmetric, two isomeric products can be produced.

Interpretation Introduction

(b)

Interpretation:

The major product among the two possible products for the given Diels-Alder reaction is to be determined.

Concept introduction:

The [4+2] cycloaddition reactions are generally known as a Diels-Alder reaction. In this reaction, a conjugated diene and a dienophile are joined via the formation of two new sigma bonds. The product is a six-membered ring. For a Diels-Alder reaction to proceed, the diene essential be able to achieve the s-cis conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Electron-donating groups attached to the diene and electron-withdrawing groups attached to the dienophile facilitates the reaction. These reactions are highly stereospecific and regioselective. Substituents that are cis to each other about the carbon-carbon double bond of the dienophile end up cis to each other in the new ring that is produced. Otherwise, the substituents end up trans to each other in the ring. Substituents attached to the terminal carbons of the diene end up cis to each other in the new ring that is produced if the double bonds of the diene are both cis or both trans. Otherwise, the substituents end up trans to each other in the ring. When the diene and dienophile are both unsymmetric, two isomeric products can be produced.

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Answer 5

Chapter 24, Problem 24.49P

Interpretation Introduction

(a)

Interpretation:

For the given Diels-Alder reaction, two constitutional isomers can be produced. The mechanism for the formation of each isomer is to be drawn.

Concept introduction:

The [4+2] cycloaddition reactions are generally known as a Diels-Alder reaction. In this reaction, a conjugated diene and a dienophile are joined via the formation of two new sigma bonds. The product is a six-membered ring. For a Diels-Alder reaction to proceed, the diene essential be able to achieve the s-cis conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Electron-donating groups attached to the diene and electron-withdrawing groups attached to the dienophile facilitates the reaction. These reactions are highly stereospecific and regioselective. Substituents that are cis to each other about the carbon-carbon double bond of the dienophile end up cis to each other in the new ring that is produced. Otherwise, the substituents end up trans to each other in the ring. Substituents attached to the terminal carbons of the diene end up cis to each other in the new ring that is produced if the double bonds of the diene are both cis or both trans. Otherwise, the substituents end up trans to each other in the ring. When the diene and dienophile are both unsymmetric, two isomeric products can be produced.

Interpretation Introduction

(b)

Interpretation:

The major product among the two possible products for the given Diels-Alder reaction is to be determined.

Concept introduction:

The [4+2] cycloaddition reactions are generally known as a Diels-Alder reaction. In this reaction, a conjugated diene and a dienophile are joined via the formation of two new sigma bonds. The product is a six-membered ring. For a Diels-Alder reaction to proceed, the diene essential be able to achieve the s-cis conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Electron-donating groups attached to the diene and electron-withdrawing groups attached to the dienophile facilitates the reaction. These reactions are highly stereospecific and regioselective. Substituents that are cis to each other about the carbon-carbon double bond of the dienophile end up cis to each other in the new ring that is produced. Otherwise, the substituents end up trans to each other in the ring. Substituents attached to the terminal carbons of the diene end up cis to each other in the new ring that is produced if the double bonds of the diene are both cis or both trans. Otherwise, the substituents end up trans to each other in the ring. When the diene and dienophile are both unsymmetric, two isomeric products can be produced.

Answer 6

Chapter 24, Problem 24.49P

Interpretation Introduction

(a)

Interpretation:

For the given Diels-Alder reaction, two constitutional isomers can be produced. The mechanism for the formation of each isomer is to be drawn.

Concept introduction:

The [4+2] cycloaddition reactions are generally known as a Diels-Alder reaction. In this reaction, a conjugated diene and a dienophile are joined via the formation of two new sigma bonds. The product is a six-membered ring. For a Diels-Alder reaction to proceed, the diene essential be able to achieve the s-cis conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Electron-donating groups attached to the diene and electron-withdrawing groups attached to the dienophile facilitates the reaction. These reactions are highly stereospecific and regioselective. Substituents that are cis to each other about the carbon-carbon double bond of the dienophile end up cis to each other in the new ring that is produced. Otherwise, the substituents end up trans to each other in the ring. Substituents attached to the terminal carbons of the diene end up cis to each other in the new ring that is produced if the double bonds of the diene are both cis or both trans. Otherwise, the substituents end up trans to each other in the ring. When the diene and dienophile are both unsymmetric, two isomeric products can be produced.

Answer 7

Chapter 24, Problem 24.49P

Interpretation Introduction

(a)

Interpretation:

For the given Diels-Alder reaction, two constitutional isomers can be produced. The mechanism for the formation of each isomer is to be drawn.

Concept introduction:

The [4+2] cycloaddition reactions are generally known as a Diels-Alder reaction. In this reaction, a conjugated diene and a dienophile are joined via the formation of two new sigma bonds. The product is a six-membered ring. For a Diels-Alder reaction to proceed, the diene essential be able to achieve the s-cis conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Electron-donating groups attached to the diene and electron-withdrawing groups attached to the dienophile facilitates the reaction. These reactions are highly stereospecific and regioselective. Substituents that are cis to each other about the carbon-carbon double bond of the dienophile end up cis to each other in the new ring that is produced. Otherwise, the substituents end up trans to each other in the ring. Substituents attached to the terminal carbons of the diene end up cis to each other in the new ring that is produced if the double bonds of the diene are both cis or both trans. Otherwise, the substituents end up trans to each other in the ring. When the diene and dienophile are both unsymmetric, two isomeric products can be produced.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The major product among the two possible products for the given Diels-Alder reaction is to be determined.

Concept introduction:

The [4+2] cycloaddition reactions are generally known as a Diels-Alder reaction. In this reaction, a conjugated diene and a dienophile are joined via the formation of two new sigma bonds. The product is a six-membered ring. For a Diels-Alder reaction to proceed, the diene essential be able to achieve the s-cis conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Electron-donating groups attached to the diene and electron-withdrawing groups attached to the dienophile facilitates the reaction. These reactions are highly stereospecific and regioselective. Substituents that are cis to each other about the carbon-carbon double bond of the dienophile end up cis to each other in the new ring that is produced. Otherwise, the substituents end up trans to each other in the ring. Substituents attached to the terminal carbons of the diene end up cis to each other in the new ring that is produced if the double bonds of the diene are both cis or both trans. Otherwise, the substituents end up trans to each other in the ring. When the diene and dienophile are both unsymmetric, two isomeric products can be produced.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The major product among the two possible products for the given Diels-Alder reaction is to be determined.

Concept introduction:

The [4+2] cycloaddition reactions are generally known as a Diels-Alder reaction. In this reaction, a conjugated diene and a dienophile are joined via the formation of two new sigma bonds. The product is a six-membered ring. For a Diels-Alder reaction to proceed, the diene essential be able to achieve the s-cis conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Electron-donating groups attached to the diene and electron-withdrawing groups attached to the dienophile facilitates the reaction. These reactions are highly stereospecific and regioselective. Substituents that are cis to each other about the carbon-carbon double bond of the dienophile end up cis to each other in the new ring that is produced. Otherwise, the substituents end up trans to each other in the ring. Substituents attached to the terminal carbons of the diene end up cis to each other in the new ring that is produced if the double bonds of the diene are both cis or both trans. Otherwise, the substituents end up trans to each other in the ring. When the diene and dienophile are both unsymmetric, two isomeric products can be produced.

Answer 10

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Answer 13

Ch. 24 - Prob. 24.1P Ch. 24 - Prob. 24.2P Ch. 24 - Prob. 24.3P Ch. 24 - Prob. 24.4P Ch. 24 - Prob. 24.5P Ch. 24 - Prob. 24.6P Ch. 24 - Prob. 24.7P Ch. 24 - Prob. 24.8P Ch. 24 - Prob. 24.9P Ch. 24 - Prob. 24.10P

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Chapter 24 Solutions