The value of Δ H ° for overall reaction of 2 -fluoro- 2 -methylpropane to 2 -fluoro- 2 -propanol should be calculated. Concept introduction: Thermodynamics is a study of energy transfers that can be done by either heat or work. The energy transferred through work involves force. When work is positive then system gains energy while when work is negative then system loses energy. Heat is not a state function and therefore change in enthalpy of reaction ( Δ H ° rxn ) has been introduced. The formula to calculate Δ H ° from bond dissociation of reactants and products is as follows: Δ H ° = Sum of D H ° of bonds broken − Sum of D H ° of bonds formed

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Answer 1

Question

Formula Formula Bond dissociation energy (BDE) is the energy required to break a bond, making it an endothermic process. BDE is calculated for a particular bond and therefore consists of fragments such as radicals since it undergoes homolytic bond cleavage. For the homolysis of a X-Y molecule, the energy of bond dissociation is calculated as the difference in the total enthalpy of formation for the reactants and products. X-Y → X + Y BDE = Δ H f X + Δ H f Y – Δ H f X-Y where, ΔHf is the heat of formation.

Chapter 7.2, Problem 7.2E

(a)

Interpretation Introduction

Interpretation: The value of ΔH° for overall reaction of 2-fluoro-2-methylpropane to 2-fluoro-2-propanol should be calculated.

Concept introduction:Thermodynamics is a study of energy transfers that can be done by either heat or work. The energy transferred through work involves force. When work is positive then system gains energy while when work is negative then system loses energy. Heat is not a state function and therefore change in enthalpy of reaction (ΔH°rxn) has been introduced. The formula to calculate ΔH° from bond dissociation of reactants and products is as follows:

ΔH°=Sum of DH° of bonds broken−Sum of DH° of bonds formed

(b)

Interpretation Introduction

Interpretation: The mechanism using curved arrows should be indicated for below reactions.

Concept introduction:Unimolecuar substitution or SN1 proceeds via a two-step mechanism. The first slow step that determines the rate is the removal of the leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecular substitution. The final step is the attack of the nucleophile on carbocation generated and the formation of racemic products.

A general SN1 reaction mechanistic pathway is illustrated as follows:

(c)

Interpretation Introduction

Interpretation: The effect observed on the rate of methanolysis when the concentration of tertiary alkyl halide taken in (i) is doubled and diethyl ether is used to dilute methanol solvent should be determined.

Concept introduction:Unimolecuar substitution or SN1 proceeds via a two-step mechanism. The first slow step that determines the rate is the removal of the leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecular substitution. The final step is the attack of the nucleophile on carbocation generated and the formation of racemic products. Rate of SN1 follows first-order kinetics and is independent of solvent or nucleophile concentration as they are not involved in first rate-determining step.

A general SN1 reaction mechanistic pathway is illustrated below:

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Give detailed answer- Provide example of compound that fulfil each criteria below. Explain why-A)1,2-disconnectionB)1,4-disconnectionC)1,5-disconnectionD)1,6-disconnection

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This problem is adapted from an experiment designed for undergraduate organic chemistry laboratories. (a) Reaction of (E)-1-(p-methoxyphenyl)propene with m-chloroperoxybenzoic acid converted the alkene to its corresponding epoxide. Give the structure, including stereochemistry, of this epoxide.(b) Assign the signals in the 1H NMR spectrum of the epoxide to the appropriate hydrogens. δ 1.4 (doublet, 3H) δ 3.8 (singlet, 3H) δ 3.0 (quartet of doublets, 1H) δ 6.9 (doublet, 2H) δ 3.5 (doublet, 1H) δ 7.2 (doublet, 2H) (c) Three signals appear in the range δ 55–60 in the 13C NMR spectrum of the epoxide. To which carbons of the epoxide do these signals correspond? (d) The epoxide is isolated only when the reaction is carried out under conditions (added Na2CO3) that ensure that the reaction mixture does not become acidic. Unless this precaution is taken, the isolated product has the molecular formula C17H17O4Cl. Suggest a reasonable structure for this product and write a reasonable mechanism…

Answer 2

Question

Formula Formula Bond dissociation energy (BDE) is the energy required to break a bond, making it an endothermic process. BDE is calculated for a particular bond and therefore consists of fragments such as radicals since it undergoes homolytic bond cleavage. For the homolysis of a X-Y molecule, the energy of bond dissociation is calculated as the difference in the total enthalpy of formation for the reactants and products. X-Y → X + Y BDE = Δ H f X + Δ H f Y – Δ H f X-Y where, ΔHf is the heat of formation.

Chapter 7.2, Problem 7.2E

(a)

Interpretation Introduction

Interpretation: The value of ΔH° for overall reaction of 2-fluoro-2-methylpropane to 2-fluoro-2-propanol should be calculated.

Concept introduction:Thermodynamics is a study of energy transfers that can be done by either heat or work. The energy transferred through work involves force. When work is positive then system gains energy while when work is negative then system loses energy. Heat is not a state function and therefore change in enthalpy of reaction (ΔH°rxn) has been introduced. The formula to calculate ΔH° from bond dissociation of reactants and products is as follows:

ΔH°=Sum of DH° of bonds broken−Sum of DH° of bonds formed

(b)

Interpretation Introduction

Interpretation: The mechanism using curved arrows should be indicated for below reactions.

Concept introduction:Unimolecuar substitution or SN1 proceeds via a two-step mechanism. The first slow step that determines the rate is the removal of the leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecular substitution. The final step is the attack of the nucleophile on carbocation generated and the formation of racemic products.

A general SN1 reaction mechanistic pathway is illustrated as follows:

(c)

Interpretation Introduction

Interpretation: The effect observed on the rate of methanolysis when the concentration of tertiary alkyl halide taken in (i) is doubled and diethyl ether is used to dilute methanol solvent should be determined.

Concept introduction:Unimolecuar substitution or SN1 proceeds via a two-step mechanism. The first slow step that determines the rate is the removal of the leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecular substitution. The final step is the attack of the nucleophile on carbocation generated and the formation of racemic products. Rate of SN1 follows first-order kinetics and is independent of solvent or nucleophile concentration as they are not involved in first rate-determining step.

A general SN1 reaction mechanistic pathway is illustrated below:

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Answer 3

Question

Formula Formula Bond dissociation energy (BDE) is the energy required to break a bond, making it an endothermic process. BDE is calculated for a particular bond and therefore consists of fragments such as radicals since it undergoes homolytic bond cleavage. For the homolysis of a X-Y molecule, the energy of bond dissociation is calculated as the difference in the total enthalpy of formation for the reactants and products. X-Y → X + Y BDE = Δ H f X + Δ H f Y – Δ H f X-Y where, ΔHf is the heat of formation.

Chapter 7.2, Problem 7.2E

(a)

Interpretation Introduction

Interpretation: The value of ΔH° for overall reaction of 2-fluoro-2-methylpropane to 2-fluoro-2-propanol should be calculated.

Concept introduction:Thermodynamics is a study of energy transfers that can be done by either heat or work. The energy transferred through work involves force. When work is positive then system gains energy while when work is negative then system loses energy. Heat is not a state function and therefore change in enthalpy of reaction (ΔH°rxn) has been introduced. The formula to calculate ΔH° from bond dissociation of reactants and products is as follows:

ΔH°=Sum of DH° of bonds broken−Sum of DH° of bonds formed

(b)

Interpretation Introduction

Interpretation: The mechanism using curved arrows should be indicated for below reactions.

Concept introduction:Unimolecuar substitution or SN1 proceeds via a two-step mechanism. The first slow step that determines the rate is the removal of the leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecular substitution. The final step is the attack of the nucleophile on carbocation generated and the formation of racemic products.

A general SN1 reaction mechanistic pathway is illustrated as follows:

(c)

Interpretation Introduction

Interpretation: The effect observed on the rate of methanolysis when the concentration of tertiary alkyl halide taken in (i) is doubled and diethyl ether is used to dilute methanol solvent should be determined.

Concept introduction:Unimolecuar substitution or SN1 proceeds via a two-step mechanism. The first slow step that determines the rate is the removal of the leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecular substitution. The final step is the attack of the nucleophile on carbocation generated and the formation of racemic products. Rate of SN1 follows first-order kinetics and is independent of solvent or nucleophile concentration as they are not involved in first rate-determining step.

A general SN1 reaction mechanistic pathway is illustrated below:

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Answer 4

Question

Formula Formula Bond dissociation energy (BDE) is the energy required to break a bond, making it an endothermic process. BDE is calculated for a particular bond and therefore consists of fragments such as radicals since it undergoes homolytic bond cleavage. For the homolysis of a X-Y molecule, the energy of bond dissociation is calculated as the difference in the total enthalpy of formation for the reactants and products. X-Y → X + Y BDE = Δ H f X + Δ H f Y – Δ H f X-Y where, ΔHf is the heat of formation.

Chapter 7.2, Problem 7.2E

(a)

Interpretation Introduction

Interpretation: The value of ΔH° for overall reaction of 2-fluoro-2-methylpropane to 2-fluoro-2-propanol should be calculated.

Concept introduction:Thermodynamics is a study of energy transfers that can be done by either heat or work. The energy transferred through work involves force. When work is positive then system gains energy while when work is negative then system loses energy. Heat is not a state function and therefore change in enthalpy of reaction (ΔH°rxn) has been introduced. The formula to calculate ΔH° from bond dissociation of reactants and products is as follows:

ΔH°=Sum of DH° of bonds broken−Sum of DH° of bonds formed

(b)

Interpretation Introduction

Interpretation: The mechanism using curved arrows should be indicated for below reactions.

Concept introduction:Unimolecuar substitution or SN1 proceeds via a two-step mechanism. The first slow step that determines the rate is the removal of the leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecular substitution. The final step is the attack of the nucleophile on carbocation generated and the formation of racemic products.

A general SN1 reaction mechanistic pathway is illustrated as follows:

(c)

Interpretation Introduction

Interpretation: The effect observed on the rate of methanolysis when the concentration of tertiary alkyl halide taken in (i) is doubled and diethyl ether is used to dilute methanol solvent should be determined.

Concept introduction:Unimolecuar substitution or SN1 proceeds via a two-step mechanism. The first slow step that determines the rate is the removal of the leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecular substitution. The final step is the attack of the nucleophile on carbocation generated and the formation of racemic products. Rate of SN1 follows first-order kinetics and is independent of solvent or nucleophile concentration as they are not involved in first rate-determining step.

A general SN1 reaction mechanistic pathway is illustrated below:

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Answer 5

Chapter 7.2, Problem 7.2E

(a)

Interpretation Introduction

Interpretation: The value of ΔH° for overall reaction of 2-fluoro-2-methylpropane to 2-fluoro-2-propanol should be calculated.

Concept introduction:Thermodynamics is a study of energy transfers that can be done by either heat or work. The energy transferred through work involves force. When work is positive then system gains energy while when work is negative then system loses energy. Heat is not a state function and therefore change in enthalpy of reaction (ΔH°rxn) has been introduced. The formula to calculate ΔH° from bond dissociation of reactants and products is as follows:

ΔH°=Sum of DH° of bonds broken−Sum of DH° of bonds formed

(b)

Interpretation Introduction

Interpretation: The mechanism using curved arrows should be indicated for below reactions.

Concept introduction:Unimolecuar substitution or SN1 proceeds via a two-step mechanism. The first slow step that determines the rate is the removal of the leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecular substitution. The final step is the attack of the nucleophile on carbocation generated and the formation of racemic products.

A general SN1 reaction mechanistic pathway is illustrated as follows:

(c)

Interpretation Introduction

Interpretation: The effect observed on the rate of methanolysis when the concentration of tertiary alkyl halide taken in (i) is doubled and diethyl ether is used to dilute methanol solvent should be determined.

Concept introduction:Unimolecuar substitution or SN1 proceeds via a two-step mechanism. The first slow step that determines the rate is the removal of the leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecular substitution. The final step is the attack of the nucleophile on carbocation generated and the formation of racemic products. Rate of SN1 follows first-order kinetics and is independent of solvent or nucleophile concentration as they are not involved in first rate-determining step.

A general SN1 reaction mechanistic pathway is illustrated below:

Answer 6

Chapter 7.2, Problem 7.2E

(a)

Interpretation Introduction

Interpretation: The value of ΔH° for overall reaction of 2-fluoro-2-methylpropane to 2-fluoro-2-propanol should be calculated.

Concept introduction:Thermodynamics is a study of energy transfers that can be done by either heat or work. The energy transferred through work involves force. When work is positive then system gains energy while when work is negative then system loses energy. Heat is not a state function and therefore change in enthalpy of reaction (ΔH°rxn) has been introduced. The formula to calculate ΔH° from bond dissociation of reactants and products is as follows:

ΔH°=Sum of DH° of bonds broken−Sum of DH° of bonds formed

Answer 7

Chapter 7.2, Problem 7.2E

(a)

Interpretation Introduction

Interpretation: The value of ΔH° for overall reaction of 2-fluoro-2-methylpropane to 2-fluoro-2-propanol should be calculated.

Concept introduction:Thermodynamics is a study of energy transfers that can be done by either heat or work. The energy transferred through work involves force. When work is positive then system gains energy while when work is negative then system loses energy. Heat is not a state function and therefore change in enthalpy of reaction (ΔH°rxn) has been introduced. The formula to calculate ΔH° from bond dissociation of reactants and products is as follows:

ΔH°=Sum of DH° of bonds broken−Sum of DH° of bonds formed

Answer 8

(b)

Interpretation Introduction

Interpretation: The mechanism using curved arrows should be indicated for below reactions.

Concept introduction:Unimolecuar substitution or SN1 proceeds via a two-step mechanism. The first slow step that determines the rate is the removal of the leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecular substitution. The final step is the attack of the nucleophile on carbocation generated and the formation of racemic products.

A general SN1 reaction mechanistic pathway is illustrated as follows:

Answer 9

(b)

Interpretation Introduction

Interpretation: The mechanism using curved arrows should be indicated for below reactions.

Concept introduction:Unimolecuar substitution or SN1 proceeds via a two-step mechanism. The first slow step that determines the rate is the removal of the leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecular substitution. The final step is the attack of the nucleophile on carbocation generated and the formation of racemic products.

A general SN1 reaction mechanistic pathway is illustrated as follows:

Answer 10

(c)

Interpretation Introduction

Interpretation: The effect observed on the rate of methanolysis when the concentration of tertiary alkyl halide taken in (i) is doubled and diethyl ether is used to dilute methanol solvent should be determined.

Concept introduction:Unimolecuar substitution or SN1 proceeds via a two-step mechanism. The first slow step that determines the rate is the removal of the leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecular substitution. The final step is the attack of the nucleophile on carbocation generated and the formation of racemic products. Rate of SN1 follows first-order kinetics and is independent of solvent or nucleophile concentration as they are not involved in first rate-determining step.

A general SN1 reaction mechanistic pathway is illustrated below:

Answer 11

(c)

Interpretation Introduction

Interpretation: The effect observed on the rate of methanolysis when the concentration of tertiary alkyl halide taken in (i) is doubled and diethyl ether is used to dilute methanol solvent should be determined.

Concept introduction:Unimolecuar substitution or SN1 proceeds via a two-step mechanism. The first slow step that determines the rate is the removal of the leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecular substitution. The final step is the attack of the nucleophile on carbocation generated and the formation of racemic products. Rate of SN1 follows first-order kinetics and is independent of solvent or nucleophile concentration as they are not involved in first rate-determining step.

A general SN1 reaction mechanistic pathway is illustrated below:

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. 7.1 - Prob. 7.1E Ch. 7.2 - Prob. 7.2E Ch. 7.3 - Prob. 7.3E Ch. 7.3 - Prob. 7.5TIY Ch. 7.4 - Prob. 7.7TIY Ch. 7.5 - Prob. 7.9TIY Ch. 7.6 - Prob. 7.10E Ch. 7.7 - Prob. 7.11E Ch. 7.7 - Prob. 7.12E Ch. 7.7 - Prob. 7.13E

Solution Summary: The author explains that thermodynamics is a study of energy transfers that can be done by either heat or work.

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