(a) Interpretation: The electron-rich sites and electron-poor sites in the given elementary steps are to be identified. Concept introduction: An atom with partial or full negative charge is an electron-rich site whereas an atom with partial or full positive charge is an electron-poor site. In an elementary step, electrons tend to flow from an electron-rich site to an electron-poor site.

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Answer 1

Question

Chapter 7, Problem 7.51P

Interpretation Introduction

(a)

Interpretation:

The electron-rich sites and electron-poor sites in the given elementary steps are to be identified.

Concept introduction:

An atom with partial or full negative charge is an electron-rich site whereas an atom with partial or full positive charge is an electron-poor site. In an elementary step, electrons tend to flow from an electron-rich site to an electron-poor site.

Interpretation Introduction

(b)

Interpretation:

In each of the given elementary steps, the appropriate curved arrows are to be drawn.

Concept introduction:

The curved arrow can be drawn from an electron-rich site to an electron-poor site to show the flow of electrons from the electron-rich site to the electron-poor site. The first curved arrow is drawn from the lone pair of the negatively charged atom of the electron-rich site to the less electronegative atom of the electron-poor site. The second curved arrow is drawn from the region between the less electronegative atom and more electronegative atom towards the more electronegative atom, indicating the breaking of the bond.

Interpretation Introduction

(c)

Interpretation:

The names of each elementary step are to be identified.

Concept introduction:

In the bimolecular substitution reaction SN2, electron pair from the electron-rich site approaches the carbon atom of the substrate to which the electron-poor atom is attached. Simultaneously, the bond between the carbon atom and the electron-poor atom breaks. The making and breaking of bonds takes place simultaneously.

In nucleophilic addition step, the nucleophile adds to the polar π bond. The nucleophile is relatively electron rich, and the polar π bond is relatively electron poor. Thus, the curved arrow drawn from the nucleophile to the polar π bond represents the flow of electrons from an electron-rich site to an electron-poor site.

In the nucleophilic elimination step, the more electronegative atom bears full negative charge or partial negative charge. This electronegative atom forms a π bond with the adjacent carbon atom by removing the leaving group.

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The reaction shown here, which converts an epoxide into a bromohydrin, is discussed in Chapter 10. It consists of the two elementary steps shown. For each step (i and ii), (a) identify all electron-rich sites and all electron-poor sites, (i) H H-Br BrO + H3C (b) draw in the appropriate curved arrows to show the bond formation and bond breaking that occur, and (c) name the elementary step. (i) BrO Но H3C H3C Br

The reaction shown here, which is discussed in Chapter 10, consists of the two elementary steps shown. For each step (i and ii), (a) identify all electron-rich sites and all electron-poor sites, (b) draw in the appropriate curved arrows to show the bond formation and bond breaking that (i) H3C OOH H3C НО occur, and (c) name the elementary step. (ii) H3C H3C OH Н-о—н + НО НО

The following reaction, which is discussed in Chapter 8, is an example of a unimolecular nucleophilic substitution (Sn1) reaction. It consists of the four elementary steps shown here. For each step (i-iv), (a) identify all electron-rich sites and all electron-poor sites, (b) draw in the appropriate curved arrows to show the bond formation and bond breaking that occur, and (c) name the elementary step. (i) H-OCH3 OH + H-OCH3 H. H (ii) ©CH2 + H,O (iii) ©CH2 CH3 + HO-CH3 (iv) CH3 CH3 + H2O-CH, + НО—СНЗ fo

Answer 2

Question

Chapter 7, Problem 7.51P

Interpretation Introduction

(a)

Interpretation:

The electron-rich sites and electron-poor sites in the given elementary steps are to be identified.

Concept introduction:

An atom with partial or full negative charge is an electron-rich site whereas an atom with partial or full positive charge is an electron-poor site. In an elementary step, electrons tend to flow from an electron-rich site to an electron-poor site.

Interpretation Introduction

(b)

Interpretation:

In each of the given elementary steps, the appropriate curved arrows are to be drawn.

Concept introduction:

The curved arrow can be drawn from an electron-rich site to an electron-poor site to show the flow of electrons from the electron-rich site to the electron-poor site. The first curved arrow is drawn from the lone pair of the negatively charged atom of the electron-rich site to the less electronegative atom of the electron-poor site. The second curved arrow is drawn from the region between the less electronegative atom and more electronegative atom towards the more electronegative atom, indicating the breaking of the bond.

Interpretation Introduction

(c)

Interpretation:

The names of each elementary step are to be identified.

Concept introduction:

In the bimolecular substitution reaction SN2, electron pair from the electron-rich site approaches the carbon atom of the substrate to which the electron-poor atom is attached. Simultaneously, the bond between the carbon atom and the electron-poor atom breaks. The making and breaking of bonds takes place simultaneously.

In nucleophilic addition step, the nucleophile adds to the polar π bond. The nucleophile is relatively electron rich, and the polar π bond is relatively electron poor. Thus, the curved arrow drawn from the nucleophile to the polar π bond represents the flow of electrons from an electron-rich site to an electron-poor site.

In the nucleophilic elimination step, the more electronegative atom bears full negative charge or partial negative charge. This electronegative atom forms a π bond with the adjacent carbon atom by removing the leaving group.

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Answer 3

Question

Chapter 7, Problem 7.51P

Interpretation Introduction

(a)

Interpretation:

The electron-rich sites and electron-poor sites in the given elementary steps are to be identified.

Concept introduction:

An atom with partial or full negative charge is an electron-rich site whereas an atom with partial or full positive charge is an electron-poor site. In an elementary step, electrons tend to flow from an electron-rich site to an electron-poor site.

Interpretation Introduction

(b)

Interpretation:

In each of the given elementary steps, the appropriate curved arrows are to be drawn.

Concept introduction:

The curved arrow can be drawn from an electron-rich site to an electron-poor site to show the flow of electrons from the electron-rich site to the electron-poor site. The first curved arrow is drawn from the lone pair of the negatively charged atom of the electron-rich site to the less electronegative atom of the electron-poor site. The second curved arrow is drawn from the region between the less electronegative atom and more electronegative atom towards the more electronegative atom, indicating the breaking of the bond.

Interpretation Introduction

(c)

Interpretation:

The names of each elementary step are to be identified.

Concept introduction:

In the bimolecular substitution reaction SN2, electron pair from the electron-rich site approaches the carbon atom of the substrate to which the electron-poor atom is attached. Simultaneously, the bond between the carbon atom and the electron-poor atom breaks. The making and breaking of bonds takes place simultaneously.

In nucleophilic addition step, the nucleophile adds to the polar π bond. The nucleophile is relatively electron rich, and the polar π bond is relatively electron poor. Thus, the curved arrow drawn from the nucleophile to the polar π bond represents the flow of electrons from an electron-rich site to an electron-poor site.

In the nucleophilic elimination step, the more electronegative atom bears full negative charge or partial negative charge. This electronegative atom forms a π bond with the adjacent carbon atom by removing the leaving group.

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Answer 4

Question

Chapter 7, Problem 7.51P

Interpretation Introduction

(a)

Interpretation:

The electron-rich sites and electron-poor sites in the given elementary steps are to be identified.

Concept introduction:

An atom with partial or full negative charge is an electron-rich site whereas an atom with partial or full positive charge is an electron-poor site. In an elementary step, electrons tend to flow from an electron-rich site to an electron-poor site.

Interpretation Introduction

(b)

Interpretation:

In each of the given elementary steps, the appropriate curved arrows are to be drawn.

Concept introduction:

The curved arrow can be drawn from an electron-rich site to an electron-poor site to show the flow of electrons from the electron-rich site to the electron-poor site. The first curved arrow is drawn from the lone pair of the negatively charged atom of the electron-rich site to the less electronegative atom of the electron-poor site. The second curved arrow is drawn from the region between the less electronegative atom and more electronegative atom towards the more electronegative atom, indicating the breaking of the bond.

Interpretation Introduction

(c)

Interpretation:

The names of each elementary step are to be identified.

Concept introduction:

In the bimolecular substitution reaction SN2, electron pair from the electron-rich site approaches the carbon atom of the substrate to which the electron-poor atom is attached. Simultaneously, the bond between the carbon atom and the electron-poor atom breaks. The making and breaking of bonds takes place simultaneously.

In nucleophilic addition step, the nucleophile adds to the polar π bond. The nucleophile is relatively electron rich, and the polar π bond is relatively electron poor. Thus, the curved arrow drawn from the nucleophile to the polar π bond represents the flow of electrons from an electron-rich site to an electron-poor site.

In the nucleophilic elimination step, the more electronegative atom bears full negative charge or partial negative charge. This electronegative atom forms a π bond with the adjacent carbon atom by removing the leaving group.

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Answer 5

Chapter 7, Problem 7.51P

Interpretation Introduction

(a)

Interpretation:

The electron-rich sites and electron-poor sites in the given elementary steps are to be identified.

Concept introduction:

An atom with partial or full negative charge is an electron-rich site whereas an atom with partial or full positive charge is an electron-poor site. In an elementary step, electrons tend to flow from an electron-rich site to an electron-poor site.

Interpretation Introduction

(b)

Interpretation:

In each of the given elementary steps, the appropriate curved arrows are to be drawn.

Concept introduction:

The curved arrow can be drawn from an electron-rich site to an electron-poor site to show the flow of electrons from the electron-rich site to the electron-poor site. The first curved arrow is drawn from the lone pair of the negatively charged atom of the electron-rich site to the less electronegative atom of the electron-poor site. The second curved arrow is drawn from the region between the less electronegative atom and more electronegative atom towards the more electronegative atom, indicating the breaking of the bond.

Interpretation Introduction

(c)

Interpretation:

The names of each elementary step are to be identified.

Concept introduction:

In the bimolecular substitution reaction SN2, electron pair from the electron-rich site approaches the carbon atom of the substrate to which the electron-poor atom is attached. Simultaneously, the bond between the carbon atom and the electron-poor atom breaks. The making and breaking of bonds takes place simultaneously.

In nucleophilic addition step, the nucleophile adds to the polar π bond. The nucleophile is relatively electron rich, and the polar π bond is relatively electron poor. Thus, the curved arrow drawn from the nucleophile to the polar π bond represents the flow of electrons from an electron-rich site to an electron-poor site.

In the nucleophilic elimination step, the more electronegative atom bears full negative charge or partial negative charge. This electronegative atom forms a π bond with the adjacent carbon atom by removing the leaving group.

Answer 6

Chapter 7, Problem 7.51P

Interpretation Introduction

(a)

Interpretation:

The electron-rich sites and electron-poor sites in the given elementary steps are to be identified.

Concept introduction:

An atom with partial or full negative charge is an electron-rich site whereas an atom with partial or full positive charge is an electron-poor site. In an elementary step, electrons tend to flow from an electron-rich site to an electron-poor site.

Answer 7

Chapter 7, Problem 7.51P

Interpretation Introduction

(a)

Interpretation:

The electron-rich sites and electron-poor sites in the given elementary steps are to be identified.

Concept introduction:

An atom with partial or full negative charge is an electron-rich site whereas an atom with partial or full positive charge is an electron-poor site. In an elementary step, electrons tend to flow from an electron-rich site to an electron-poor site.

Answer 8

Interpretation Introduction

(b)

Interpretation:

In each of the given elementary steps, the appropriate curved arrows are to be drawn.

Concept introduction:

The curved arrow can be drawn from an electron-rich site to an electron-poor site to show the flow of electrons from the electron-rich site to the electron-poor site. The first curved arrow is drawn from the lone pair of the negatively charged atom of the electron-rich site to the less electronegative atom of the electron-poor site. The second curved arrow is drawn from the region between the less electronegative atom and more electronegative atom towards the more electronegative atom, indicating the breaking of the bond.

Answer 9

Interpretation Introduction

(b)

Interpretation:

In each of the given elementary steps, the appropriate curved arrows are to be drawn.

Concept introduction:

The curved arrow can be drawn from an electron-rich site to an electron-poor site to show the flow of electrons from the electron-rich site to the electron-poor site. The first curved arrow is drawn from the lone pair of the negatively charged atom of the electron-rich site to the less electronegative atom of the electron-poor site. The second curved arrow is drawn from the region between the less electronegative atom and more electronegative atom towards the more electronegative atom, indicating the breaking of the bond.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The names of each elementary step are to be identified.

Concept introduction:

In the bimolecular substitution reaction SN2, electron pair from the electron-rich site approaches the carbon atom of the substrate to which the electron-poor atom is attached. Simultaneously, the bond between the carbon atom and the electron-poor atom breaks. The making and breaking of bonds takes place simultaneously.

In nucleophilic addition step, the nucleophile adds to the polar π bond. The nucleophile is relatively electron rich, and the polar π bond is relatively electron poor. Thus, the curved arrow drawn from the nucleophile to the polar π bond represents the flow of electrons from an electron-rich site to an electron-poor site.

In the nucleophilic elimination step, the more electronegative atom bears full negative charge or partial negative charge. This electronegative atom forms a π bond with the adjacent carbon atom by removing the leaving group.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The names of each elementary step are to be identified.

Concept introduction:

In the bimolecular substitution reaction SN2, electron pair from the electron-rich site approaches the carbon atom of the substrate to which the electron-poor atom is attached. Simultaneously, the bond between the carbon atom and the electron-poor atom breaks. The making and breaking of bonds takes place simultaneously.

In nucleophilic addition step, the nucleophile adds to the polar π bond. The nucleophile is relatively electron rich, and the polar π bond is relatively electron poor. Thus, the curved arrow drawn from the nucleophile to the polar π bond represents the flow of electrons from an electron-rich site to an electron-poor site.

In the nucleophilic elimination step, the more electronegative atom bears full negative charge or partial negative charge. This electronegative atom forms a π bond with the adjacent carbon atom by removing the leaving group.

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. 7 - Prob. 7.1P Ch. 7 - Prob. 7.2P Ch. 7 - Prob. 7.3P Ch. 7 - Prob. 7.4P Ch. 7 - Prob. 7.5P Ch. 7 - Prob. 7.6P Ch. 7 - Prob. 7.7P Ch. 7 - Prob. 7.8P Ch. 7 - Prob. 7.9P Ch. 7 - Prob. 7.10P

Solution Summary: The author explains that electrons flow from an electron-rich site to a negatively charged phosphorous atom in an elementary step.

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