(a) Interpretation: It is to be determined whether the given product is of direct or conjugate addition to an α,β-unsaturated carbonyl. Concept introduction: In the case of α,β- unsaturated carbonyl compounds, the weak resonance contributor with separated charges generates a small partial positive charge on the β carbon due to the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the β carbon. The polar π bonds of α,β- unsaturated carbonyl compounds are susceptible to nucleophilic attack at both the electron-poor atom of the polar π bond and the β 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 α,β- unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar carbonyl bond, and when 1, 4-addition takes place, the nucleophile adds to the β carbon and reversibly to the carbonyl group. So the product of the direct addition is alcohol on acidic workup while in conjugate addition, the carbonyl group is reverted and the nucleophile adds to the β carbon.

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Answer 1

Question

Chapter 17, Problem 17.14YT

Interpretation Introduction

(a)

Interpretation:

It is to be determined whether the given product is of direct or conjugate addition to an α,β-unsaturated carbonyl.

Concept introduction:

In the case of α,β- unsaturated carbonyl compounds, the weak resonance contributor with separated charges generates a small partial positive charge on the β carbon due to the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the β carbon. The polar π bonds of α,β- unsaturated carbonyl compounds are susceptible to nucleophilic attack at both the electron-poor atom of the polar π bond and the β 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 α,β- unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar carbonyl bond, and when 1, 4-addition takes place, the nucleophile adds to the β carbon and reversibly to the carbonyl group. So the product of the direct addition is alcohol on acidic workup while in conjugate addition, the carbonyl group is reverted and the nucleophile adds to the β carbon.

Interpretation Introduction

(b)

Interpretation:

It is to be determined if the given product is of direct or conjugate addition to an α,β-unsaturated carbonyl.

Concept introduction:

In the case of α,β- unsaturated carbonyl compounds, the weak resonance contributor with separated charges generates a small partial positive charge on the β carbon due to the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the β carbon. The polar π bonds of α,β- unsaturated carbonyl compounds are susceptible to nucleophilic attack at both the electron-poor atom of the polar π bond and the β 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 α,β- unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar carbonyl bond, and when 1, 4-addition takes place, the nucleophile adds to the β carbon and reversibly to the carbonyl group. So the product of the direct addition is alcohol on acidic workup while in conjugate addition, the carbonyl group is reverted and the nucleophile adds to the β carbon.

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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…

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Answer 2

Question

Chapter 17, Problem 17.14YT

Interpretation Introduction

(a)

Interpretation:

It is to be determined whether the given product is of direct or conjugate addition to an α,β-unsaturated carbonyl.

Concept introduction:

In the case of α,β- unsaturated carbonyl compounds, the weak resonance contributor with separated charges generates a small partial positive charge on the β carbon due to the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the β carbon. The polar π bonds of α,β- unsaturated carbonyl compounds are susceptible to nucleophilic attack at both the electron-poor atom of the polar π bond and the β 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 α,β- unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar carbonyl bond, and when 1, 4-addition takes place, the nucleophile adds to the β carbon and reversibly to the carbonyl group. So the product of the direct addition is alcohol on acidic workup while in conjugate addition, the carbonyl group is reverted and the nucleophile adds to the β carbon.

Interpretation Introduction

(b)

Interpretation:

It is to be determined if the given product is of direct or conjugate addition to an α,β-unsaturated carbonyl.

Concept introduction:

In the case of α,β- unsaturated carbonyl compounds, the weak resonance contributor with separated charges generates a small partial positive charge on the β carbon due to the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the β carbon. The polar π bonds of α,β- unsaturated carbonyl compounds are susceptible to nucleophilic attack at both the electron-poor atom of the polar π bond and the β 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 α,β- unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar carbonyl bond, and when 1, 4-addition takes place, the nucleophile adds to the β carbon and reversibly to the carbonyl group. So the product of the direct addition is alcohol on acidic workup while in conjugate addition, the carbonyl group is reverted and the nucleophile adds to the β carbon.

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Answer 3

Question

Chapter 17, Problem 17.14YT

Interpretation Introduction

(a)

Interpretation:

It is to be determined whether the given product is of direct or conjugate addition to an α,β-unsaturated carbonyl.

Concept introduction:

In the case of α,β- unsaturated carbonyl compounds, the weak resonance contributor with separated charges generates a small partial positive charge on the β carbon due to the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the β carbon. The polar π bonds of α,β- unsaturated carbonyl compounds are susceptible to nucleophilic attack at both the electron-poor atom of the polar π bond and the β 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 α,β- unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar carbonyl bond, and when 1, 4-addition takes place, the nucleophile adds to the β carbon and reversibly to the carbonyl group. So the product of the direct addition is alcohol on acidic workup while in conjugate addition, the carbonyl group is reverted and the nucleophile adds to the β carbon.

Interpretation Introduction

(b)

Interpretation:

It is to be determined if the given product is of direct or conjugate addition to an α,β-unsaturated carbonyl.

Concept introduction:

In the case of α,β- unsaturated carbonyl compounds, the weak resonance contributor with separated charges generates a small partial positive charge on the β carbon due to the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the β carbon. The polar π bonds of α,β- unsaturated carbonyl compounds are susceptible to nucleophilic attack at both the electron-poor atom of the polar π bond and the β 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 α,β- unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar carbonyl bond, and when 1, 4-addition takes place, the nucleophile adds to the β carbon and reversibly to the carbonyl group. So the product of the direct addition is alcohol on acidic workup while in conjugate addition, the carbonyl group is reverted and the nucleophile adds to the β carbon.

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Answer 4

Question

Chapter 17, Problem 17.14YT

Interpretation Introduction

(a)

Interpretation:

It is to be determined whether the given product is of direct or conjugate addition to an α,β-unsaturated carbonyl.

Concept introduction:

In the case of α,β- unsaturated carbonyl compounds, the weak resonance contributor with separated charges generates a small partial positive charge on the β carbon due to the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the β carbon. The polar π bonds of α,β- unsaturated carbonyl compounds are susceptible to nucleophilic attack at both the electron-poor atom of the polar π bond and the β 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 α,β- unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar carbonyl bond, and when 1, 4-addition takes place, the nucleophile adds to the β carbon and reversibly to the carbonyl group. So the product of the direct addition is alcohol on acidic workup while in conjugate addition, the carbonyl group is reverted and the nucleophile adds to the β carbon.

Interpretation Introduction

(b)

Interpretation:

It is to be determined if the given product is of direct or conjugate addition to an α,β-unsaturated carbonyl.

Concept introduction:

In the case of α,β- unsaturated carbonyl compounds, the weak resonance contributor with separated charges generates a small partial positive charge on the β carbon due to the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the β carbon. The polar π bonds of α,β- unsaturated carbonyl compounds are susceptible to nucleophilic attack at both the electron-poor atom of the polar π bond and the β 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 α,β- unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar carbonyl bond, and when 1, 4-addition takes place, the nucleophile adds to the β carbon and reversibly to the carbonyl group. So the product of the direct addition is alcohol on acidic workup while in conjugate addition, the carbonyl group is reverted and the nucleophile adds to the β carbon.

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Answer 5

Chapter 17, Problem 17.14YT

Interpretation Introduction

(a)

Interpretation:

It is to be determined whether the given product is of direct or conjugate addition to an α,β-unsaturated carbonyl.

Concept introduction:

In the case of α,β- unsaturated carbonyl compounds, the weak resonance contributor with separated charges generates a small partial positive charge on the β carbon due to the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the β carbon. The polar π bonds of α,β- unsaturated carbonyl compounds are susceptible to nucleophilic attack at both the electron-poor atom of the polar π bond and the β 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 α,β- unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar carbonyl bond, and when 1, 4-addition takes place, the nucleophile adds to the β carbon and reversibly to the carbonyl group. So the product of the direct addition is alcohol on acidic workup while in conjugate addition, the carbonyl group is reverted and the nucleophile adds to the β carbon.

Interpretation Introduction

(b)

Interpretation:

It is to be determined if the given product is of direct or conjugate addition to an α,β-unsaturated carbonyl.

Concept introduction:

In the case of α,β- unsaturated carbonyl compounds, the weak resonance contributor with separated charges generates a small partial positive charge on the β carbon due to the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the β carbon. The polar π bonds of α,β- unsaturated carbonyl compounds are susceptible to nucleophilic attack at both the electron-poor atom of the polar π bond and the β 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 α,β- unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar carbonyl bond, and when 1, 4-addition takes place, the nucleophile adds to the β carbon and reversibly to the carbonyl group. So the product of the direct addition is alcohol on acidic workup while in conjugate addition, the carbonyl group is reverted and the nucleophile adds to the β carbon.

Answer 6

Chapter 17, Problem 17.14YT

Interpretation Introduction

(a)

Interpretation:

It is to be determined whether the given product is of direct or conjugate addition to an α,β-unsaturated carbonyl.

Concept introduction:

In the case of α,β- unsaturated carbonyl compounds, the weak resonance contributor with separated charges generates a small partial positive charge on the β carbon due to the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the β carbon. The polar π bonds of α,β- unsaturated carbonyl compounds are susceptible to nucleophilic attack at both the electron-poor atom of the polar π bond and the β 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 α,β- unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar carbonyl bond, and when 1, 4-addition takes place, the nucleophile adds to the β carbon and reversibly to the carbonyl group. So the product of the direct addition is alcohol on acidic workup while in conjugate addition, the carbonyl group is reverted and the nucleophile adds to the β carbon.

Answer 7

Chapter 17, Problem 17.14YT

Interpretation Introduction

(a)

Interpretation:

It is to be determined whether the given product is of direct or conjugate addition to an α,β-unsaturated carbonyl.

Concept introduction:

In the case of α,β- unsaturated carbonyl compounds, the weak resonance contributor with separated charges generates a small partial positive charge on the β carbon due to the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the β carbon. The polar π bonds of α,β- unsaturated carbonyl compounds are susceptible to nucleophilic attack at both the electron-poor atom of the polar π bond and the β 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 α,β- unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar carbonyl bond, and when 1, 4-addition takes place, the nucleophile adds to the β carbon and reversibly to the carbonyl group. So the product of the direct addition is alcohol on acidic workup while in conjugate addition, the carbonyl group is reverted and the nucleophile adds to the β carbon.

Answer 8

Interpretation Introduction

(b)

Interpretation:

It is to be determined if the given product is of direct or conjugate addition to an α,β-unsaturated carbonyl.

Concept introduction:

In the case of α,β- unsaturated carbonyl compounds, the weak resonance contributor with separated charges generates a small partial positive charge on the β carbon due to the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the β carbon. The polar π bonds of α,β- unsaturated carbonyl compounds are susceptible to nucleophilic attack at both the electron-poor atom of the polar π bond and the β 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 α,β- unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar carbonyl bond, and when 1, 4-addition takes place, the nucleophile adds to the β carbon and reversibly to the carbonyl group. So the product of the direct addition is alcohol on acidic workup while in conjugate addition, the carbonyl group is reverted and the nucleophile adds to the β carbon.

Answer 9

Interpretation Introduction

(b)

Interpretation:

It is to be determined if the given product is of direct or conjugate addition to an α,β-unsaturated carbonyl.

Concept introduction:

In the case of α,β- unsaturated carbonyl compounds, the weak resonance contributor with separated charges generates a small partial positive charge on the β carbon due to the resonance hybrid. Thus, a nucleophile can attack at either the carbonyl carbon or the β carbon. The polar π bonds of α,β- unsaturated carbonyl compounds are susceptible to nucleophilic attack at both the electron-poor atom of the polar π bond and the β 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 α,β- unsaturated polar π bond dominates if the nucleophile adds irreversibly to the polar carbonyl bond, and when 1, 4-addition takes place, the nucleophile adds to the β carbon and reversibly to the carbonyl group. So the product of the direct addition is alcohol on acidic workup while in conjugate addition, the carbonyl group is reverted and the nucleophile adds to the β carbon.

Answer 10

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Answer 13

Ch. 17 - Prob. 17.1P Ch. 17 - Prob. 17.2P Ch. 17 - Prob. 17.3P Ch. 17 - Prob. 17.4P Ch. 17 - Prob. 17.5P Ch. 17 - Prob. 17.6P Ch. 17 - Prob. 17.7P Ch. 17 - Prob. 17.8P Ch. 17 - Prob. 17.9P Ch. 17 - Prob. 17.10P

Solution Summary: The author explains whether the given product is of direct or conjugate addition to an,-unsaturated carbonyl.

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