(a) Interpretation: For each step of the given reaction, which converts an epoxide into a bromohydrin, all electron-rich sites and electron-poor sites are to be identified. Concept introduction: An atom with partial or full negative charge is called an electron-rich site whereas an atom with partial or full positive charge is called an electron-poor site. An electron-rich atom has a lone pair of electrons whereas an electron-poor atom lacks an octet. 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 7.48P

Interpretation Introduction

(a)

Interpretation:

For each step of the given reaction, which converts an epoxide into a bromohydrin, all electron-rich sites and electron-poor sites are to be identified.

Concept introduction:

An atom with partial or full negative charge is called an electron-rich site whereas an atom with partial or full positive charge is called an electron-poor site. An electron-rich atom has a lone pair of electrons whereas an electron-poor atom lacks an octet. In an elementary step, electrons tend to flow from an electron-rich site to an electron-poor site.

Interpretation Introduction

(b)

Interpretation:

Appropriate curved arrows are to be drawn to show the bond formation and bond breaking that occur in each step of the given reaction, which converts an epoxide into a bromohydrin.

Concept introduction:

In an elementary step, electrons tend to flow from an electron-rich site to an electron-poor site. One curved arrow is drawn from the lone pair of the electron-rich atom to the H attached to the electron-poor site to show the formation of a bond. A second curved arrow is drawn starting from the middle of the broken bond to the atom on which the lone pair ends up to indicate the breaking of the bond.

Interpretation Introduction

(c)

Interpretation:

Each step of the given reaction, which converts an epoxide into a bromohydrin, is to be named.

Concept introduction:

An elementary step in which a proton is transferred from an electron-poor site to an electron-rich site and one bond is broken and another is formed simultaneously is called the proton transfer step. In the SN2 type of reaction, the lone pair of electrons from the electron-rich site approaches the carbon atom of the substrate to which the electron-poor atom is attached. Since the negatively charged atom (nucleophile) starts forming a bond with this carbon atom, the bond between the electron poor atom and carbon atom breaks. The making and breaking of bonds take place simultaneously.

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1,4-Dimethyl-1,3-cyclohexadiene can undergo 1,2- or 1,4-addition with hydrogen halides. (a) 1,2-Addition i. Draw the carbocation intermediate(s) formed during the 1,2-addition of hydrobromic acid to 1,4-dimethyl-1,3-cyclohexadiene. ii. What is the major 1,2-addition product formed during the reaction in (i)? (b) 1,4-Addition i. Draw the carbocation intermediate(s) formed during the 1,4-addition of hydrobromic acid to 1,4-dimethyl-1,3-cyclohexadiene. ii. What is the major 1,4-addition product formed from the reaction in (i)? (c) What is the kinetic product from the reaction of one mole of hydrobromic acid with 1,4-dimethyl-1,3-cyclohexadiene? Explain your reasoning. (d) What is the thermodynamic product from the reaction of one mole of hydrobro-mic acid with 1,4-dimethyl-1,3-cyclohexadiene? Explain your reasoning. (e) What major product will result when 1,4-dimethyl-1,3-cyclohexadiene is treated with one mole of hydrobromic acid at - 78 deg * C ? Explain your reasoning.

Answer 2

Question

Chapter 7, Problem 7.48P

Interpretation Introduction

(a)

Interpretation:

For each step of the given reaction, which converts an epoxide into a bromohydrin, all electron-rich sites and electron-poor sites are to be identified.

Concept introduction:

An atom with partial or full negative charge is called an electron-rich site whereas an atom with partial or full positive charge is called an electron-poor site. An electron-rich atom has a lone pair of electrons whereas an electron-poor atom lacks an octet. In an elementary step, electrons tend to flow from an electron-rich site to an electron-poor site.

Interpretation Introduction

(b)

Interpretation:

Appropriate curved arrows are to be drawn to show the bond formation and bond breaking that occur in each step of the given reaction, which converts an epoxide into a bromohydrin.

Concept introduction:

In an elementary step, electrons tend to flow from an electron-rich site to an electron-poor site. One curved arrow is drawn from the lone pair of the electron-rich atom to the H attached to the electron-poor site to show the formation of a bond. A second curved arrow is drawn starting from the middle of the broken bond to the atom on which the lone pair ends up to indicate the breaking of the bond.

Interpretation Introduction

(c)

Interpretation:

Each step of the given reaction, which converts an epoxide into a bromohydrin, is to be named.

Concept introduction:

An elementary step in which a proton is transferred from an electron-poor site to an electron-rich site and one bond is broken and another is formed simultaneously is called the proton transfer step. In the SN2 type of reaction, the lone pair of electrons from the electron-rich site approaches the carbon atom of the substrate to which the electron-poor atom is attached. Since the negatively charged atom (nucleophile) starts forming a bond with this carbon atom, the bond between the electron poor atom and carbon atom breaks. The making and breaking of bonds take place simultaneously.

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Answer 3

Question

Chapter 7, Problem 7.48P

Interpretation Introduction

(a)

Interpretation:

For each step of the given reaction, which converts an epoxide into a bromohydrin, all electron-rich sites and electron-poor sites are to be identified.

Concept introduction:

An atom with partial or full negative charge is called an electron-rich site whereas an atom with partial or full positive charge is called an electron-poor site. An electron-rich atom has a lone pair of electrons whereas an electron-poor atom lacks an octet. In an elementary step, electrons tend to flow from an electron-rich site to an electron-poor site.

Interpretation Introduction

(b)

Interpretation:

Appropriate curved arrows are to be drawn to show the bond formation and bond breaking that occur in each step of the given reaction, which converts an epoxide into a bromohydrin.

Concept introduction:

In an elementary step, electrons tend to flow from an electron-rich site to an electron-poor site. One curved arrow is drawn from the lone pair of the electron-rich atom to the H attached to the electron-poor site to show the formation of a bond. A second curved arrow is drawn starting from the middle of the broken bond to the atom on which the lone pair ends up to indicate the breaking of the bond.

Interpretation Introduction

(c)

Interpretation:

Each step of the given reaction, which converts an epoxide into a bromohydrin, is to be named.

Concept introduction:

An elementary step in which a proton is transferred from an electron-poor site to an electron-rich site and one bond is broken and another is formed simultaneously is called the proton transfer step. In the SN2 type of reaction, the lone pair of electrons from the electron-rich site approaches the carbon atom of the substrate to which the electron-poor atom is attached. Since the negatively charged atom (nucleophile) starts forming a bond with this carbon atom, the bond between the electron poor atom and carbon atom breaks. The making and breaking of bonds take place simultaneously.

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Answer 4

Question

Chapter 7, Problem 7.48P

Interpretation Introduction

(a)

Interpretation:

For each step of the given reaction, which converts an epoxide into a bromohydrin, all electron-rich sites and electron-poor sites are to be identified.

Concept introduction:

An atom with partial or full negative charge is called an electron-rich site whereas an atom with partial or full positive charge is called an electron-poor site. An electron-rich atom has a lone pair of electrons whereas an electron-poor atom lacks an octet. In an elementary step, electrons tend to flow from an electron-rich site to an electron-poor site.

Interpretation Introduction

(b)

Interpretation:

Appropriate curved arrows are to be drawn to show the bond formation and bond breaking that occur in each step of the given reaction, which converts an epoxide into a bromohydrin.

Concept introduction:

In an elementary step, electrons tend to flow from an electron-rich site to an electron-poor site. One curved arrow is drawn from the lone pair of the electron-rich atom to the H attached to the electron-poor site to show the formation of a bond. A second curved arrow is drawn starting from the middle of the broken bond to the atom on which the lone pair ends up to indicate the breaking of the bond.

Interpretation Introduction

(c)

Interpretation:

Each step of the given reaction, which converts an epoxide into a bromohydrin, is to be named.

Concept introduction:

An elementary step in which a proton is transferred from an electron-poor site to an electron-rich site and one bond is broken and another is formed simultaneously is called the proton transfer step. In the SN2 type of reaction, the lone pair of electrons from the electron-rich site approaches the carbon atom of the substrate to which the electron-poor atom is attached. Since the negatively charged atom (nucleophile) starts forming a bond with this carbon atom, the bond between the electron poor atom and carbon atom breaks. The making and breaking of bonds take place simultaneously.

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Answer 5

Chapter 7, Problem 7.48P

Interpretation Introduction

(a)

Interpretation:

For each step of the given reaction, which converts an epoxide into a bromohydrin, all electron-rich sites and electron-poor sites are to be identified.

Concept introduction:

An atom with partial or full negative charge is called an electron-rich site whereas an atom with partial or full positive charge is called an electron-poor site. An electron-rich atom has a lone pair of electrons whereas an electron-poor atom lacks an octet. In an elementary step, electrons tend to flow from an electron-rich site to an electron-poor site.

Interpretation Introduction

(b)

Interpretation:

Appropriate curved arrows are to be drawn to show the bond formation and bond breaking that occur in each step of the given reaction, which converts an epoxide into a bromohydrin.

Concept introduction:

In an elementary step, electrons tend to flow from an electron-rich site to an electron-poor site. One curved arrow is drawn from the lone pair of the electron-rich atom to the H attached to the electron-poor site to show the formation of a bond. A second curved arrow is drawn starting from the middle of the broken bond to the atom on which the lone pair ends up to indicate the breaking of the bond.

Interpretation Introduction

(c)

Interpretation:

Each step of the given reaction, which converts an epoxide into a bromohydrin, is to be named.

Concept introduction:

An elementary step in which a proton is transferred from an electron-poor site to an electron-rich site and one bond is broken and another is formed simultaneously is called the proton transfer step. In the SN2 type of reaction, the lone pair of electrons from the electron-rich site approaches the carbon atom of the substrate to which the electron-poor atom is attached. Since the negatively charged atom (nucleophile) starts forming a bond with this carbon atom, the bond between the electron poor atom and carbon atom breaks. The making and breaking of bonds take place simultaneously.

Answer 6

Chapter 7, Problem 7.48P

Interpretation Introduction

(a)

Interpretation:

For each step of the given reaction, which converts an epoxide into a bromohydrin, all electron-rich sites and electron-poor sites are to be identified.

Concept introduction:

An atom with partial or full negative charge is called an electron-rich site whereas an atom with partial or full positive charge is called an electron-poor site. An electron-rich atom has a lone pair of electrons whereas an electron-poor atom lacks an octet. In an elementary step, electrons tend to flow from an electron-rich site to an electron-poor site.

Answer 7

Chapter 7, Problem 7.48P

Interpretation Introduction

(a)

Interpretation:

For each step of the given reaction, which converts an epoxide into a bromohydrin, all electron-rich sites and electron-poor sites are to be identified.

Concept introduction:

An atom with partial or full negative charge is called an electron-rich site whereas an atom with partial or full positive charge is called an electron-poor site. An electron-rich atom has a lone pair of electrons whereas an electron-poor atom lacks an octet. In an elementary step, electrons tend to flow from an electron-rich site to an electron-poor site.

Answer 8

Interpretation Introduction

(b)

Interpretation:

Appropriate curved arrows are to be drawn to show the bond formation and bond breaking that occur in each step of the given reaction, which converts an epoxide into a bromohydrin.

Concept introduction:

In an elementary step, electrons tend to flow from an electron-rich site to an electron-poor site. One curved arrow is drawn from the lone pair of the electron-rich atom to the H attached to the electron-poor site to show the formation of a bond. A second curved arrow is drawn starting from the middle of the broken bond to the atom on which the lone pair ends up to indicate the breaking of the bond.

Answer 9

Interpretation Introduction

(b)

Interpretation:

Appropriate curved arrows are to be drawn to show the bond formation and bond breaking that occur in each step of the given reaction, which converts an epoxide into a bromohydrin.

Concept introduction:

In an elementary step, electrons tend to flow from an electron-rich site to an electron-poor site. One curved arrow is drawn from the lone pair of the electron-rich atom to the H attached to the electron-poor site to show the formation of a bond. A second curved arrow is drawn starting from the middle of the broken bond to the atom on which the lone pair ends up to indicate the breaking of the bond.

Answer 10

Interpretation Introduction

(c)

Interpretation:

Each step of the given reaction, which converts an epoxide into a bromohydrin, is to be named.

Concept introduction:

An elementary step in which a proton is transferred from an electron-poor site to an electron-rich site and one bond is broken and another is formed simultaneously is called the proton transfer step. In the SN2 type of reaction, the lone pair of electrons from the electron-rich site approaches the carbon atom of the substrate to which the electron-poor atom is attached. Since the negatively charged atom (nucleophile) starts forming a bond with this carbon atom, the bond between the electron poor atom and carbon atom breaks. The making and breaking of bonds take place simultaneously.

Answer 11

Interpretation Introduction

(c)

Interpretation:

Each step of the given reaction, which converts an epoxide into a bromohydrin, is to be named.

Concept introduction:

An elementary step in which a proton is transferred from an electron-poor site to an electron-rich site and one bond is broken and another is formed simultaneously is called the proton transfer step. In the SN2 type of reaction, the lone pair of electrons from the electron-rich site approaches the carbon atom of the substrate to which the electron-poor atom is attached. Since the negatively charged atom (nucleophile) starts forming a bond with this carbon atom, the bond between the electron poor atom and carbon atom breaks. The making and breaking of bonds take place simultaneously.

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 non-electronspoor site in an elementary step.

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Chapter 7 Solutions