(a) Interpretation: For the given reaction, the major product and reaction mechanism is to be drawn. Concept introduction: The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Question

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Answer 1

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 17, Problem 17.60P

Interpretation Introduction

(a)

Interpretation:

For the given reaction, the major product and reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Expert Solution

Answer to Problem 17.60P

The nucleophile adds reversibly and undergoes a 1, 4-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 1

Explanation of Solution

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon.

In this reaction, both carbonyl carbon as well as beta carbon are electrophilic. Here the nucleophile adds reversibly; therefore, this reaction undergoes 1, 4-addition. In this reaction, O− atom forms in the nucleophilic addition step. It is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 2

Here the enol tautomerizes back to the ketone via back to back proton transfer steps. It is represented as below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 3

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Interpretation Introduction

(b)

Interpretation:

For the given reaction, the major product and the reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Expert Solution

Answer to Problem 17.60P

The nucleophile adds irreversibly and undergoes a 1, 2-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 4

Explanation of Solution

A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

In this reaction, the nucleophile adds irreversibly; hence this reaction undergoes direction addition (1, 2-addition). In this reaction, O− atom forms in the nucleophilic addition step. It is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 5

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Interpretation Introduction

(c)

Interpretation:

For the given reaction, the major product and the reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Expert Solution

Answer to Problem 17.60P

The nucleophile adds irreversibly and undergoes a 1, 2-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 6

Explanation of Solution

A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

In this reaction, the nucleophile adds irreversibly; hence this reaction undergoes direct addition (1, 2-addition). Here O− atom forms in the nucleophilic addition step. The O^- is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 7

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Interpretation Introduction

(d)

Interpretation:

For the given reaction, the major product and the reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Expert Solution

Answer to Problem 17.60P

The nucleophile adds irreversibly and undergoes a 1, 4-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 8

Explanation of Solution

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon.

In this reaction, both carbonyl carbon as well as beta carbon are electrophilic. In this reaction, the nucleophile adds reversibly; therefore this reaction undergoes 1, 4-addition. In this reaction, O− atom forms in the nucleophilic addition step. It is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 9

Here the enol tautomerizes back to the ketone via back to back proton transfer steps. It is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 10

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Interpretation Introduction

(e)

Interpretation:

For the given reaction, the major product and the reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Expert Solution

Answer to Problem 17.60P

The nucleophile adds irreversibly and undergoes a 1, 4-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 11

Explanation of Solution

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon.

In this reaction, both carbonyl carbon as well as beta carbon are electrophilic. In this reaction, the nucleophile adds reversibly; therefore this reaction undergoes 1, 4-addition. In this reaction, O− atom forms in the nucleophilic addition step. It is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 12

Here the enol tautomerizes back to the ketone via back to back proton transfer steps. It is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 13

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

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Choose the Lewis structure for the compound below: H2CCHOCH2CH(CH3)2 HH H :d H H H C. Η H H HH H H H H. H H H HH H H H H H- H H H C-H H H HHHH

Each of the highlighted carbon atoms is connected to hydrogen atoms.

く Complete the reaction in the drawing area below by adding the major products to the right-hand side. If there won't be any products, because nothing will happen under these reaction conditions, check the box under the drawing area instead. Note: if the products contain one or more pairs of enantiomers, don't worry about drawing each enantiomer with dash and wedge bonds. Just draw one molecule to represent each pair of enantiomers, using line bonds at the chiral center. More... No reaction. Explanation Check O + G 1. Na O Me Click and drag to start drawing a structure. 2. H + 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Accessibility 000 Ar P

Answer 2

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 17, Problem 17.60P

Interpretation Introduction

(a)

Interpretation:

For the given reaction, the major product and reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Expert Solution

Answer to Problem 17.60P

The nucleophile adds reversibly and undergoes a 1, 4-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 1

Explanation of Solution

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon.

In this reaction, both carbonyl carbon as well as beta carbon are electrophilic. Here the nucleophile adds reversibly; therefore, this reaction undergoes 1, 4-addition. In this reaction, O− atom forms in the nucleophilic addition step. It is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 2

Here the enol tautomerizes back to the ketone via back to back proton transfer steps. It is represented as below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 3

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Interpretation Introduction

(b)

Interpretation:

For the given reaction, the major product and the reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Expert Solution

Answer to Problem 17.60P

The nucleophile adds irreversibly and undergoes a 1, 2-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 4

Explanation of Solution

A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

In this reaction, the nucleophile adds irreversibly; hence this reaction undergoes direction addition (1, 2-addition). In this reaction, O− atom forms in the nucleophilic addition step. It is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 5

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Interpretation Introduction

(c)

Interpretation:

For the given reaction, the major product and the reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Expert Solution

Answer to Problem 17.60P

The nucleophile adds irreversibly and undergoes a 1, 2-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 6

Explanation of Solution

A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

In this reaction, the nucleophile adds irreversibly; hence this reaction undergoes direct addition (1, 2-addition). Here O− atom forms in the nucleophilic addition step. The O^- is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 7

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Interpretation Introduction

(d)

Interpretation:

For the given reaction, the major product and the reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Expert Solution

Answer to Problem 17.60P

The nucleophile adds irreversibly and undergoes a 1, 4-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 8

Explanation of Solution

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon.

In this reaction, both carbonyl carbon as well as beta carbon are electrophilic. In this reaction, the nucleophile adds reversibly; therefore this reaction undergoes 1, 4-addition. In this reaction, O− atom forms in the nucleophilic addition step. It is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 9

Here the enol tautomerizes back to the ketone via back to back proton transfer steps. It is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 10

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Interpretation Introduction

(e)

Interpretation:

For the given reaction, the major product and the reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Expert Solution

Answer to Problem 17.60P

The nucleophile adds irreversibly and undergoes a 1, 4-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 11

Explanation of Solution

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon.

In this reaction, both carbonyl carbon as well as beta carbon are electrophilic. In this reaction, the nucleophile adds reversibly; therefore this reaction undergoes 1, 4-addition. In this reaction, O− atom forms in the nucleophilic addition step. It is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 12

Here the enol tautomerizes back to the ketone via back to back proton transfer steps. It is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 13

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 17, Problem 17.60P

Interpretation Introduction

(a)

Interpretation:

For the given reaction, the major product and reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Expert Solution

Answer to Problem 17.60P

The nucleophile adds reversibly and undergoes a 1, 4-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 1

Explanation of Solution

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon.

In this reaction, both carbonyl carbon as well as beta carbon are electrophilic. Here the nucleophile adds reversibly; therefore, this reaction undergoes 1, 4-addition. In this reaction, O− atom forms in the nucleophilic addition step. It is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 2

Here the enol tautomerizes back to the ketone via back to back proton transfer steps. It is represented as below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 3

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Interpretation Introduction

(b)

Interpretation:

For the given reaction, the major product and the reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Expert Solution

Answer to Problem 17.60P

The nucleophile adds irreversibly and undergoes a 1, 2-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 4

Explanation of Solution

A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

In this reaction, the nucleophile adds irreversibly; hence this reaction undergoes direction addition (1, 2-addition). In this reaction, O− atom forms in the nucleophilic addition step. It is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 5

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Interpretation Introduction

(c)

Interpretation:

For the given reaction, the major product and the reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Expert Solution

Answer to Problem 17.60P

The nucleophile adds irreversibly and undergoes a 1, 2-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 6

Explanation of Solution

A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

In this reaction, the nucleophile adds irreversibly; hence this reaction undergoes direct addition (1, 2-addition). Here O− atom forms in the nucleophilic addition step. The O^- is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 7

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Interpretation Introduction

(d)

Interpretation:

For the given reaction, the major product and the reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Expert Solution

Answer to Problem 17.60P

The nucleophile adds irreversibly and undergoes a 1, 4-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 8

Explanation of Solution

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon.

In this reaction, both carbonyl carbon as well as beta carbon are electrophilic. In this reaction, the nucleophile adds reversibly; therefore this reaction undergoes 1, 4-addition. In this reaction, O− atom forms in the nucleophilic addition step. It is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 9

Here the enol tautomerizes back to the ketone via back to back proton transfer steps. It is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 10

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Interpretation Introduction

(e)

Interpretation:

For the given reaction, the major product and the reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Expert Solution

Answer to Problem 17.60P

The nucleophile adds irreversibly and undergoes a 1, 4-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 11

Explanation of Solution

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon.

In this reaction, both carbonyl carbon as well as beta carbon are electrophilic. In this reaction, the nucleophile adds reversibly; therefore this reaction undergoes 1, 4-addition. In this reaction, O− atom forms in the nucleophilic addition step. It is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 12

Here the enol tautomerizes back to the ketone via back to back proton transfer steps. It is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 13

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

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Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 17, Problem 17.60P

Interpretation Introduction

(a)

Interpretation:

For the given reaction, the major product and reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Expert Solution

Answer to Problem 17.60P

The nucleophile adds reversibly and undergoes a 1, 4-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 1

Explanation of Solution

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon.

In this reaction, both carbonyl carbon as well as beta carbon are electrophilic. Here the nucleophile adds reversibly; therefore, this reaction undergoes 1, 4-addition. In this reaction, O− atom forms in the nucleophilic addition step. It is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 2

Here the enol tautomerizes back to the ketone via back to back proton transfer steps. It is represented as below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 3

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Interpretation Introduction

(b)

Interpretation:

For the given reaction, the major product and the reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Expert Solution

Answer to Problem 17.60P

The nucleophile adds irreversibly and undergoes a 1, 2-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 4

Explanation of Solution

A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

In this reaction, the nucleophile adds irreversibly; hence this reaction undergoes direction addition (1, 2-addition). In this reaction, O− atom forms in the nucleophilic addition step. It is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 5

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Interpretation Introduction

(c)

Interpretation:

For the given reaction, the major product and the reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Expert Solution

Answer to Problem 17.60P

The nucleophile adds irreversibly and undergoes a 1, 2-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 6

Explanation of Solution

A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

In this reaction, the nucleophile adds irreversibly; hence this reaction undergoes direct addition (1, 2-addition). Here O− atom forms in the nucleophilic addition step. The O^- is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 7

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Interpretation Introduction

(d)

Interpretation:

For the given reaction, the major product and the reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Expert Solution

Answer to Problem 17.60P

The nucleophile adds irreversibly and undergoes a 1, 4-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 8

Explanation of Solution

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon.

In this reaction, both carbonyl carbon as well as beta carbon are electrophilic. In this reaction, the nucleophile adds reversibly; therefore this reaction undergoes 1, 4-addition. In this reaction, O− atom forms in the nucleophilic addition step. It is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 9

Here the enol tautomerizes back to the ketone via back to back proton transfer steps. It is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 10

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Interpretation Introduction

(e)

Interpretation:

For the given reaction, the major product and the reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Expert Solution

Answer to Problem 17.60P

The nucleophile adds irreversibly and undergoes a 1, 4-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 11

Explanation of Solution

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon.

In this reaction, both carbonyl carbon as well as beta carbon are electrophilic. In this reaction, the nucleophile adds reversibly; therefore this reaction undergoes 1, 4-addition. In this reaction, O− atom forms in the nucleophilic addition step. It is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 12

Here the enol tautomerizes back to the ketone via back to back proton transfer steps. It is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 13

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 5

Chapter 17, Problem 17.60P

Interpretation Introduction

(a)

Interpretation:

For the given reaction, the major product and reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Expert Solution

Answer to Problem 17.60P

The nucleophile adds reversibly and undergoes a 1, 4-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 1

Explanation of Solution

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon.

In this reaction, both carbonyl carbon as well as beta carbon are electrophilic. Here the nucleophile adds reversibly; therefore, this reaction undergoes 1, 4-addition. In this reaction, O− atom forms in the nucleophilic addition step. It is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 2

Here the enol tautomerizes back to the ketone via back to back proton transfer steps. It is represented as below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 3

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Interpretation Introduction

(b)

Interpretation:

For the given reaction, the major product and the reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Expert Solution

Answer to Problem 17.60P

The nucleophile adds irreversibly and undergoes a 1, 2-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 4

Explanation of Solution

A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

In this reaction, the nucleophile adds irreversibly; hence this reaction undergoes direction addition (1, 2-addition). In this reaction, O− atom forms in the nucleophilic addition step. It is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 5

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Interpretation Introduction

(c)

Interpretation:

For the given reaction, the major product and the reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Expert Solution

Answer to Problem 17.60P

The nucleophile adds irreversibly and undergoes a 1, 2-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 6

Explanation of Solution

A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

In this reaction, the nucleophile adds irreversibly; hence this reaction undergoes direct addition (1, 2-addition). Here O− atom forms in the nucleophilic addition step. The O^- is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 7

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Interpretation Introduction

(d)

Interpretation:

For the given reaction, the major product and the reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Expert Solution

Answer to Problem 17.60P

The nucleophile adds irreversibly and undergoes a 1, 4-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 8

Explanation of Solution

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon.

In this reaction, both carbonyl carbon as well as beta carbon are electrophilic. In this reaction, the nucleophile adds reversibly; therefore this reaction undergoes 1, 4-addition. In this reaction, O− atom forms in the nucleophilic addition step. It is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 9

Here the enol tautomerizes back to the ketone via back to back proton transfer steps. It is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 10

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Interpretation Introduction

(e)

Interpretation:

For the given reaction, the major product and the reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Expert Solution

Answer to Problem 17.60P

The nucleophile adds irreversibly and undergoes a 1, 4-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 11

Explanation of Solution

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon.

In this reaction, both carbonyl carbon as well as beta carbon are electrophilic. In this reaction, the nucleophile adds reversibly; therefore this reaction undergoes 1, 4-addition. In this reaction, O− atom forms in the nucleophilic addition step. It is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 12

Here the enol tautomerizes back to the ketone via back to back proton transfer steps. It is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 13

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Answer 6

Chapter 17, Problem 17.60P

Interpretation Introduction

(a)

Interpretation:

For the given reaction, the major product and reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Expert Solution

Answer to Problem 17.60P

The nucleophile adds reversibly and undergoes a 1, 4-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 1

Explanation of Solution

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon.

In this reaction, both carbonyl carbon as well as beta carbon are electrophilic. Here the nucleophile adds reversibly; therefore, this reaction undergoes 1, 4-addition. In this reaction, O− atom forms in the nucleophilic addition step. It is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 2

Here the enol tautomerizes back to the ketone via back to back proton transfer steps. It is represented as below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 3

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Answer 7

Chapter 17, Problem 17.60P

Interpretation Introduction

(a)

Interpretation:

For the given reaction, the major product and reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Answer 8

Expert Solution

Answer to Problem 17.60P

The nucleophile adds reversibly and undergoes a 1, 4-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 1

Answer 9

Expert Solution

Answer 10

Expert Solution

Answer 11

Expert Solution

Answer 12

Explanation of Solution

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon.

In this reaction, both carbonyl carbon as well as beta carbon are electrophilic. Here the nucleophile adds reversibly; therefore, this reaction undergoes 1, 4-addition. In this reaction, O− atom forms in the nucleophilic addition step. It is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 2

Here the enol tautomerizes back to the ketone via back to back proton transfer steps. It is represented as below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 3

Answer 13

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Answer 14

Interpretation Introduction

(b)

Interpretation:

For the given reaction, the major product and the reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Expert Solution

Answer to Problem 17.60P

The nucleophile adds irreversibly and undergoes a 1, 2-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 4

Explanation of Solution

A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

In this reaction, the nucleophile adds irreversibly; hence this reaction undergoes direction addition (1, 2-addition). In this reaction, O− atom forms in the nucleophilic addition step. It is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 5

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Answer 15

Interpretation Introduction

(b)

Interpretation:

For the given reaction, the major product and the reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Answer 16

Expert Solution

Answer to Problem 17.60P

The nucleophile adds irreversibly and undergoes a 1, 2-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 4

Answer 17

Expert Solution

Answer 18

Expert Solution

Answer 19

Expert Solution

Answer 20

Explanation of Solution

A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

In this reaction, the nucleophile adds irreversibly; hence this reaction undergoes direction addition (1, 2-addition). In this reaction, O− atom forms in the nucleophilic addition step. It is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 5

Answer 21

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Answer 22

Interpretation Introduction

(c)

Interpretation:

For the given reaction, the major product and the reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Expert Solution

Answer to Problem 17.60P

The nucleophile adds irreversibly and undergoes a 1, 2-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 6

Explanation of Solution

A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

In this reaction, the nucleophile adds irreversibly; hence this reaction undergoes direct addition (1, 2-addition). Here O− atom forms in the nucleophilic addition step. The O^- is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 7

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Answer 23

Interpretation Introduction

(c)

Interpretation:

For the given reaction, the major product and the reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Answer 24

Expert Solution

Answer to Problem 17.60P

The nucleophile adds irreversibly and undergoes a 1, 2-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 6

Answer 25

Expert Solution

Answer 26

Expert Solution

Answer 27

Expert Solution

Answer 28

Explanation of Solution

A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

In this reaction, the nucleophile adds irreversibly; hence this reaction undergoes direct addition (1, 2-addition). Here O− atom forms in the nucleophilic addition step. The O^- is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 7

Answer 29

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Answer 30

Interpretation Introduction

(d)

Interpretation:

For the given reaction, the major product and the reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Expert Solution

Answer to Problem 17.60P

The nucleophile adds irreversibly and undergoes a 1, 4-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 8

Explanation of Solution

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon.

In this reaction, both carbonyl carbon as well as beta carbon are electrophilic. In this reaction, the nucleophile adds reversibly; therefore this reaction undergoes 1, 4-addition. In this reaction, O− atom forms in the nucleophilic addition step. It is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 9

Here the enol tautomerizes back to the ketone via back to back proton transfer steps. It is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 10

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Answer 31

Interpretation Introduction

(d)

Interpretation:

For the given reaction, the major product and the reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Answer 32

Expert Solution

Answer to Problem 17.60P

The nucleophile adds irreversibly and undergoes a 1, 4-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 8

Answer 33

Expert Solution

Answer 34

Expert Solution

Answer 35

Expert Solution

Answer 36

Explanation of Solution

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon.

In this reaction, both carbonyl carbon as well as beta carbon are electrophilic. In this reaction, the nucleophile adds reversibly; therefore this reaction undergoes 1, 4-addition. In this reaction, O− atom forms in the nucleophilic addition step. It is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 9

Here the enol tautomerizes back to the ketone via back to back proton transfer steps. It is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 10

Answer 37

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Answer 38

Interpretation Introduction

(e)

Interpretation:

For the given reaction, the major product and the reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Expert Solution

Answer to Problem 17.60P

The nucleophile adds irreversibly and undergoes a 1, 4-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 11

Explanation of Solution

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon.

In this reaction, both carbonyl carbon as well as beta carbon are electrophilic. In this reaction, the nucleophile adds reversibly; therefore this reaction undergoes 1, 4-addition. In this reaction, O− atom forms in the nucleophilic addition step. It is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 12

Here the enol tautomerizes back to the ketone via back to back proton transfer steps. It is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 13

Conclusion

From the location of the electrophilic carbon, the major product for the given reaction is predicted, and the reaction mechanism is drawn.

Answer 39

Interpretation Introduction

(e)

Interpretation:

For the given reaction, the major product and the reaction mechanism is to be drawn.

Concept introduction:

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon. Attack at the carbonyl carbon yields the direct addition (or 1, 2—addition) product whereas attack at the beta carbon yields the conjugate addition (or 1, 4-addition). Direct addition to an alpha, beta-unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar π bond. Otherwise, conjugate addition is favored.

Answer 40

Expert Solution

Answer to Problem 17.60P

The nucleophile adds irreversibly and undergoes a 1, 4-addition reaction.

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 11

Answer 41

Expert Solution

Answer 42

Expert Solution

Answer 43

Expert Solution

Answer 44

Explanation of Solution

The weak resonance contributor with separated charges generates a small partial positive charge on the beta carbon in the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the beta carbon. A polar π bond that is alpha, beta-unsaturated is susceptible to a nucleophilic attack at both the electron-poor atom of the polar π bond and the beta carbon.

In this reaction, both carbonyl carbon as well as beta carbon are electrophilic. In this reaction, the nucleophile adds reversibly; therefore this reaction undergoes 1, 4-addition. In this reaction, O− atom forms in the nucleophilic addition step. It is then protonated in a subsequent proton transfer reaction to form uncharged alcohol. The reaction mechanism is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 12

Here the enol tautomerizes back to the ketone via back to back proton transfer steps. It is shown below:

Organic Chemistry: Principles And Mechanisms, Chapter 17, Problem 17.60P , additional homework tip 13