Major organic product of monobromination of pentane at 125 ° C should be identified. Concept introduction: The monobromination performed with ultraviolet light proceeds via radical chain mechanism. Tertiary C – H bonds react in halogenations more readily than secondary those in turn are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation. The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

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Answer 1

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Chapter 3, Problem 31P

(a)

Interpretation Introduction

Interpretation: Major organic product of monobromination of pentane at 125 °C should be identified.

Concept introduction: The monobromination performed with ultraviolet light proceeds via radical chain mechanism.

Tertiary C – H bonds react in halogenations more readily than secondary those in turn are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

(b)

Interpretation Introduction

Interpretation: All Newman projections of major brominated products in staggered conformations should be drawn.

Concept introduction: Various interconvertible forms that result from rotation around the C–C bind in ethane are termed as conformer. To depict such conformation Newman projections are written. These are obtained by conversion of hashed-wedged line structure simply when molecule is viewed in a plane along the C–C as illustrated as follows:

Thus in Newman's projection of simple ethane molecule the “front” C is depicted as intersection of three bonds with three attached H . The other three bonds connect to the large circle corresponding to “back” carbon in C–C bond.

(c)

Interpretation Introduction

Interpretation: Qualitative plot of potential energy against torsional angle for C2–C3 rotation in this molecule should be drawn.

Concept introduction: As rotation is carried out along C – C axis, energy changes occur due to bond rotation from staggered to eclipsed conformation. This change amounts to torsional strain. Energy difference between eclipsed and staggered conformations corresponds to barrier that must be overcome for rotation. This is also termed as activation energy.

The potential energy shows peaks and falls. This corresponds to transition from staggered and eclipsed conformation molecule adopts with each 60 ° rotation as illustrated in lateral view below:

Staggered conformation that has substituents on both carbons farthest apart is regarded most stable due to least torsional strain, whereas the eclipsed has large amount of torsional strain due to steric repulsions. Therefore in potential-energy diagram, peak corresponds to eclipsed while the valley corresponds to stable staggered conformation.

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Write a conformational structure for 1,2,3-trimethylcyclohexane in which all the methyl groups are axial and then show its more stable conformation.

Two constitutional isomers with molecular formula C2H6O have boiling points of –23.6°C and 78.4°C. Draw both constitutional isomers of C2H6O (or provide the name). Identify the structural class of each. Match the constitutional isomers you have drawn to the boiling points provided above, and explain your reasoning.

Sketch a potential energy diagram for rotation around a carbon–carbon bond in propane. Identify each potential energy maximum and minimum with a structural formula that shows the conformation of propane at that point. Does your diagram more closely resemble that of ethane or of butane? Would you expect the activation energy for bond rotation in propane to be more than or less than that of ethane? Of butane?

Answer 2

Question

Chapter 3, Problem 31P

(a)

Interpretation Introduction

Interpretation: Major organic product of monobromination of pentane at 125 °C should be identified.

Concept introduction: The monobromination performed with ultraviolet light proceeds via radical chain mechanism.

Tertiary C – H bonds react in halogenations more readily than secondary those in turn are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

(b)

Interpretation Introduction

Interpretation: All Newman projections of major brominated products in staggered conformations should be drawn.

Concept introduction: Various interconvertible forms that result from rotation around the C–C bind in ethane are termed as conformer. To depict such conformation Newman projections are written. These are obtained by conversion of hashed-wedged line structure simply when molecule is viewed in a plane along the C–C as illustrated as follows:

Thus in Newman's projection of simple ethane molecule the “front” C is depicted as intersection of three bonds with three attached H . The other three bonds connect to the large circle corresponding to “back” carbon in C–C bond.

(c)

Interpretation Introduction

Interpretation: Qualitative plot of potential energy against torsional angle for C2–C3 rotation in this molecule should be drawn.

Concept introduction: As rotation is carried out along C – C axis, energy changes occur due to bond rotation from staggered to eclipsed conformation. This change amounts to torsional strain. Energy difference between eclipsed and staggered conformations corresponds to barrier that must be overcome for rotation. This is also termed as activation energy.

The potential energy shows peaks and falls. This corresponds to transition from staggered and eclipsed conformation molecule adopts with each 60 ° rotation as illustrated in lateral view below:

Staggered conformation that has substituents on both carbons farthest apart is regarded most stable due to least torsional strain, whereas the eclipsed has large amount of torsional strain due to steric repulsions. Therefore in potential-energy diagram, peak corresponds to eclipsed while the valley corresponds to stable staggered conformation.

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Answer 3

Question

Chapter 3, Problem 31P

(a)

Interpretation Introduction

Interpretation: Major organic product of monobromination of pentane at 125 °C should be identified.

Concept introduction: The monobromination performed with ultraviolet light proceeds via radical chain mechanism.

Tertiary C – H bonds react in halogenations more readily than secondary those in turn are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

(b)

Interpretation Introduction

Interpretation: All Newman projections of major brominated products in staggered conformations should be drawn.

Concept introduction: Various interconvertible forms that result from rotation around the C–C bind in ethane are termed as conformer. To depict such conformation Newman projections are written. These are obtained by conversion of hashed-wedged line structure simply when molecule is viewed in a plane along the C–C as illustrated as follows:

Thus in Newman's projection of simple ethane molecule the “front” C is depicted as intersection of three bonds with three attached H . The other three bonds connect to the large circle corresponding to “back” carbon in C–C bond.

(c)

Interpretation Introduction

Interpretation: Qualitative plot of potential energy against torsional angle for C2–C3 rotation in this molecule should be drawn.

Concept introduction: As rotation is carried out along C – C axis, energy changes occur due to bond rotation from staggered to eclipsed conformation. This change amounts to torsional strain. Energy difference between eclipsed and staggered conformations corresponds to barrier that must be overcome for rotation. This is also termed as activation energy.

The potential energy shows peaks and falls. This corresponds to transition from staggered and eclipsed conformation molecule adopts with each 60 ° rotation as illustrated in lateral view below:

Staggered conformation that has substituents on both carbons farthest apart is regarded most stable due to least torsional strain, whereas the eclipsed has large amount of torsional strain due to steric repulsions. Therefore in potential-energy diagram, peak corresponds to eclipsed while the valley corresponds to stable staggered conformation.

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Answer 4

Question

Chapter 3, Problem 31P

(a)

Interpretation Introduction

Interpretation: Major organic product of monobromination of pentane at 125 °C should be identified.

Concept introduction: The monobromination performed with ultraviolet light proceeds via radical chain mechanism.

Tertiary C – H bonds react in halogenations more readily than secondary those in turn are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

(b)

Interpretation Introduction

Interpretation: All Newman projections of major brominated products in staggered conformations should be drawn.

Concept introduction: Various interconvertible forms that result from rotation around the C–C bind in ethane are termed as conformer. To depict such conformation Newman projections are written. These are obtained by conversion of hashed-wedged line structure simply when molecule is viewed in a plane along the C–C as illustrated as follows:

Thus in Newman's projection of simple ethane molecule the “front” C is depicted as intersection of three bonds with three attached H . The other three bonds connect to the large circle corresponding to “back” carbon in C–C bond.

(c)

Interpretation Introduction

Interpretation: Qualitative plot of potential energy against torsional angle for C2–C3 rotation in this molecule should be drawn.

Concept introduction: As rotation is carried out along C – C axis, energy changes occur due to bond rotation from staggered to eclipsed conformation. This change amounts to torsional strain. Energy difference between eclipsed and staggered conformations corresponds to barrier that must be overcome for rotation. This is also termed as activation energy.

The potential energy shows peaks and falls. This corresponds to transition from staggered and eclipsed conformation molecule adopts with each 60 ° rotation as illustrated in lateral view below:

Staggered conformation that has substituents on both carbons farthest apart is regarded most stable due to least torsional strain, whereas the eclipsed has large amount of torsional strain due to steric repulsions. Therefore in potential-energy diagram, peak corresponds to eclipsed while the valley corresponds to stable staggered conformation.

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Answer 5

Chapter 3, Problem 31P

(a)

Interpretation Introduction

Interpretation: Major organic product of monobromination of pentane at 125 °C should be identified.

Concept introduction: The monobromination performed with ultraviolet light proceeds via radical chain mechanism.

Tertiary C – H bonds react in halogenations more readily than secondary those in turn are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

(b)

Interpretation Introduction

Interpretation: All Newman projections of major brominated products in staggered conformations should be drawn.

Concept introduction: Various interconvertible forms that result from rotation around the C–C bind in ethane are termed as conformer. To depict such conformation Newman projections are written. These are obtained by conversion of hashed-wedged line structure simply when molecule is viewed in a plane along the C–C as illustrated as follows:

Thus in Newman's projection of simple ethane molecule the “front” C is depicted as intersection of three bonds with three attached H . The other three bonds connect to the large circle corresponding to “back” carbon in C–C bond.

(c)

Interpretation Introduction

Interpretation: Qualitative plot of potential energy against torsional angle for C2–C3 rotation in this molecule should be drawn.

Concept introduction: As rotation is carried out along C – C axis, energy changes occur due to bond rotation from staggered to eclipsed conformation. This change amounts to torsional strain. Energy difference between eclipsed and staggered conformations corresponds to barrier that must be overcome for rotation. This is also termed as activation energy.

The potential energy shows peaks and falls. This corresponds to transition from staggered and eclipsed conformation molecule adopts with each 60 ° rotation as illustrated in lateral view below:

Staggered conformation that has substituents on both carbons farthest apart is regarded most stable due to least torsional strain, whereas the eclipsed has large amount of torsional strain due to steric repulsions. Therefore in potential-energy diagram, peak corresponds to eclipsed while the valley corresponds to stable staggered conformation.

Answer 6

Chapter 3, Problem 31P

(a)

Interpretation Introduction

Interpretation: Major organic product of monobromination of pentane at 125 °C should be identified.

Concept introduction: The monobromination performed with ultraviolet light proceeds via radical chain mechanism.

Tertiary C – H bonds react in halogenations more readily than secondary those in turn are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

Answer 7

Chapter 3, Problem 31P

(a)

Interpretation Introduction

Interpretation: Major organic product of monobromination of pentane at 125 °C should be identified.

Concept introduction: The monobromination performed with ultraviolet light proceeds via radical chain mechanism.

Tertiary C – H bonds react in halogenations more readily than secondary those in turn are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

Answer 8

(b)

Interpretation Introduction

Interpretation: All Newman projections of major brominated products in staggered conformations should be drawn.

Concept introduction: Various interconvertible forms that result from rotation around the C–C bind in ethane are termed as conformer. To depict such conformation Newman projections are written. These are obtained by conversion of hashed-wedged line structure simply when molecule is viewed in a plane along the C–C as illustrated as follows:

Thus in Newman's projection of simple ethane molecule the “front” C is depicted as intersection of three bonds with three attached H . The other three bonds connect to the large circle corresponding to “back” carbon in C–C bond.

Answer 9

(b)

Interpretation Introduction

Interpretation: All Newman projections of major brominated products in staggered conformations should be drawn.

Concept introduction: Various interconvertible forms that result from rotation around the C–C bind in ethane are termed as conformer. To depict such conformation Newman projections are written. These are obtained by conversion of hashed-wedged line structure simply when molecule is viewed in a plane along the C–C as illustrated as follows:

Thus in Newman's projection of simple ethane molecule the “front” C is depicted as intersection of three bonds with three attached H . The other three bonds connect to the large circle corresponding to “back” carbon in C–C bond.

Answer 10

(c)

Interpretation Introduction

Interpretation: Qualitative plot of potential energy against torsional angle for C2–C3 rotation in this molecule should be drawn.

Concept introduction: As rotation is carried out along C – C axis, energy changes occur due to bond rotation from staggered to eclipsed conformation. This change amounts to torsional strain. Energy difference between eclipsed and staggered conformations corresponds to barrier that must be overcome for rotation. This is also termed as activation energy.

The potential energy shows peaks and falls. This corresponds to transition from staggered and eclipsed conformation molecule adopts with each 60 ° rotation as illustrated in lateral view below:

Staggered conformation that has substituents on both carbons farthest apart is regarded most stable due to least torsional strain, whereas the eclipsed has large amount of torsional strain due to steric repulsions. Therefore in potential-energy diagram, peak corresponds to eclipsed while the valley corresponds to stable staggered conformation.

Answer 11

(c)

Interpretation Introduction

Interpretation: Qualitative plot of potential energy against torsional angle for C2–C3 rotation in this molecule should be drawn.

Concept introduction: As rotation is carried out along C – C axis, energy changes occur due to bond rotation from staggered to eclipsed conformation. This change amounts to torsional strain. Energy difference between eclipsed and staggered conformations corresponds to barrier that must be overcome for rotation. This is also termed as activation energy.

The potential energy shows peaks and falls. This corresponds to transition from staggered and eclipsed conformation molecule adopts with each 60 ° rotation as illustrated in lateral view below:

Staggered conformation that has substituents on both carbons farthest apart is regarded most stable due to least torsional strain, whereas the eclipsed has large amount of torsional strain due to steric repulsions. Therefore in potential-energy diagram, peak corresponds to eclipsed while the valley corresponds to stable staggered conformation.

Answer 12

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Answer 15

Ch. 3.1 - Prob. 3.2TIY Ch. 3.1 - Prob. 3.3E Ch. 3.4 - Prob. 3.5TIY Ch. 3.5 - Prob. 3.6E Ch. 3.7 - Prob. 3.7E Ch. 3.7 - Prob. 3.9TIY Ch. 3.9 - Prob. 3.11TIY Ch. 3.11 - Prob. 3.12E Ch. 3 - Prob. 15P Ch. 3 - Prob. 16P

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