(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 7.50P

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 is drawn from electron rich site to an electron poor site to show the flow of electrons from electron-rich site to electron-poor site. The first curved arrow is drawn from the lone pair of negatively charged atom of electron-rich site to the less electronegative atom of 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 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 substrate to which the electron-poor atom is attached. As the anion (nucleophile) forms a bond with this carbon atom, the bond between the carbon atom and the electron-poor atom breaks. The making and breaking of bonds takes place simultaneously.

An elementary step in which a proton is transferred from electron-poor site to electron- rich site and one bond is broken and another is formed simultaneously is called proton transfer step.

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The following reaction, which is discussed in Chapter 17, 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 occur, and (c) name the elementary step. (i) (C6H5)3P + + BrO H Br H P(C6H5)3 (ii) (CH),CO + (CH3)3CH H P(C6H5)3

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

Many primary amines, RNH2, where R is a carboncontainingfragment such as CH3, CH3CH2, and so on,undergo reactions where the transition state is tetrahedral.(a) Draw a hybrid orbital picture to visualize thebonding at the nitrogen in a primary amine (just use a Catom for “R”). (b) What kind of reactant with a primaryamine can produce a tetrahedral intermediate?

Answer 2

Question

Chapter 7, Problem 7.50P

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 is drawn from electron rich site to an electron poor site to show the flow of electrons from electron-rich site to electron-poor site. The first curved arrow is drawn from the lone pair of negatively charged atom of electron-rich site to the less electronegative atom of 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 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 substrate to which the electron-poor atom is attached. As the anion (nucleophile) forms a bond with this carbon atom, the bond between the carbon atom and the electron-poor atom breaks. The making and breaking of bonds takes place simultaneously.

An elementary step in which a proton is transferred from electron-poor site to electron- rich site and one bond is broken and another is formed simultaneously is called proton transfer step.

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Answer 3

Question

Chapter 7, Problem 7.50P

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 is drawn from electron rich site to an electron poor site to show the flow of electrons from electron-rich site to electron-poor site. The first curved arrow is drawn from the lone pair of negatively charged atom of electron-rich site to the less electronegative atom of 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 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 substrate to which the electron-poor atom is attached. As the anion (nucleophile) forms a bond with this carbon atom, the bond between the carbon atom and the electron-poor atom breaks. The making and breaking of bonds takes place simultaneously.

An elementary step in which a proton is transferred from electron-poor site to electron- rich site and one bond is broken and another is formed simultaneously is called proton transfer step.

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Answer 4

Question

Chapter 7, Problem 7.50P

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 is drawn from electron rich site to an electron poor site to show the flow of electrons from electron-rich site to electron-poor site. The first curved arrow is drawn from the lone pair of negatively charged atom of electron-rich site to the less electronegative atom of 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 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 substrate to which the electron-poor atom is attached. As the anion (nucleophile) forms a bond with this carbon atom, the bond between the carbon atom and the electron-poor atom breaks. The making and breaking of bonds takes place simultaneously.

An elementary step in which a proton is transferred from electron-poor site to electron- rich site and one bond is broken and another is formed simultaneously is called proton transfer step.

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Answer 5

Chapter 7, Problem 7.50P

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 is drawn from electron rich site to an electron poor site to show the flow of electrons from electron-rich site to electron-poor site. The first curved arrow is drawn from the lone pair of negatively charged atom of electron-rich site to the less electronegative atom of 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 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 substrate to which the electron-poor atom is attached. As the anion (nucleophile) forms a bond with this carbon atom, the bond between the carbon atom and the electron-poor atom breaks. The making and breaking of bonds takes place simultaneously.

An elementary step in which a proton is transferred from electron-poor site to electron- rich site and one bond is broken and another is formed simultaneously is called proton transfer step.

Answer 6

Chapter 7, Problem 7.50P

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 7.50P

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 is drawn from electron rich site to an electron poor site to show the flow of electrons from electron-rich site to electron-poor site. The first curved arrow is drawn from the lone pair of negatively charged atom of electron-rich site to the less electronegative atom of 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 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 is drawn from electron rich site to an electron poor site to show the flow of electrons from electron-rich site to electron-poor site. The first curved arrow is drawn from the lone pair of negatively charged atom of electron-rich site to the less electronegative atom of 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 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 substrate to which the electron-poor atom is attached. As the anion (nucleophile) forms a bond with this carbon atom, the bond between the carbon atom and the electron-poor atom breaks. The making and breaking of bonds takes place simultaneously.

An elementary step in which a proton is transferred from electron-poor site to electron- rich site and one bond is broken and another is formed simultaneously is called proton transfer step.

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 substrate to which the electron-poor atom is attached. As the anion (nucleophile) forms a bond with this carbon atom, the bond between the carbon atom and the electron-poor atom breaks. The making and breaking of bonds takes place simultaneously.

An elementary step in which a proton is transferred from electron-poor site to electron- rich site and one bond is broken and another is formed simultaneously is called proton transfer step.

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 negative-charged atom. The curved arrows are drawn from electron rich to electron poor sites.

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