(a) Interpretation: The product formed by the thermal electrocyclic ring opening or ring closure to the given compound is to be predicted. The process has to be labeled as conrotatory and disrotatory and the stereochemistry around stereogenic center and double bond is to be indicated. Concept introduction: Electrocyclic reactions involve ring opening or ring closure in a conjugated polyene. According to Woodward-Hoffmann rules, the polyene containing even number of bonds in photochemical conditions undergoes reaction in disrotatory fashion and polyene containing odd number of bonds undergo reaction in conrotatory fashion.

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Answer 1

Question

Chapter 27, Problem 27.30P

Interpretation Introduction

(a)

Interpretation: The product formed by the thermal electrocyclic ring opening or ring closure to the given compound is to be predicted. The process has to be labeled as conrotatory and disrotatory and the stereochemistry around stereogenic center and double bond is to be indicated.

Concept introduction: Electrocyclic reactions involve ring opening or ring closure in a conjugated polyene. According to Woodward-Hoffmann rules, the polyene containing even number of bonds in photochemical conditions undergoes reaction in disrotatory fashion and polyene containing odd number of bonds undergo reaction in conrotatory fashion.

Interpretation Introduction

(b)

Interpretation: The product formed by the thermal electrocyclic ring opening or ring closure to the given compound is to be predicted. The process has to be labeled as conrotatory and disrotatory and the stereochemistry around stereogenic center and double bond is to be indicated.

Concept introduction: Electrocyclic reactions involve ring opening or ring closure in a conjugated polyene. According to Woodward-Hoffmann rules, the polyene containing even number of bonds in photochemical conditions undergoes reaction in disrotatory fashion and polyene containing odd number of bonds undergo reaction in conrotatory fashion.

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What product is formed when each compound undergoes thermal electrocyclic ring opening or ring closure? Label each process as conrotatory or disrotatory and clearly indicate the stereochemistry around tetrahedral stereogenic centers and double bonds. а. b.

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Problem 5.37 Compare the physical properties of the three stereoisomers of 1,3-dimethylcyclopentane. A B C three stereolsomers of 1,3-dimethylcyclopentane a. How do the boiling points of A and B compare? What about those of A and C? b. Characterize a solution of each of the following as optically active or optically inactive: pure A; pure B; pure C; an equal mixture of A and B; an equal mixture of A and C. c. A reaction forms a 1:1:1 mixture of A, B, and C. If this mixture is distilled, how many fractions would be obtained? Which fractions would be optically active and which would be optically inactive?

Answer 2

Question

Chapter 27, Problem 27.30P

Interpretation Introduction

(a)

Interpretation: The product formed by the thermal electrocyclic ring opening or ring closure to the given compound is to be predicted. The process has to be labeled as conrotatory and disrotatory and the stereochemistry around stereogenic center and double bond is to be indicated.

Concept introduction: Electrocyclic reactions involve ring opening or ring closure in a conjugated polyene. According to Woodward-Hoffmann rules, the polyene containing even number of bonds in photochemical conditions undergoes reaction in disrotatory fashion and polyene containing odd number of bonds undergo reaction in conrotatory fashion.

Interpretation Introduction

(b)

Interpretation: The product formed by the thermal electrocyclic ring opening or ring closure to the given compound is to be predicted. The process has to be labeled as conrotatory and disrotatory and the stereochemistry around stereogenic center and double bond is to be indicated.

Concept introduction: Electrocyclic reactions involve ring opening or ring closure in a conjugated polyene. According to Woodward-Hoffmann rules, the polyene containing even number of bonds in photochemical conditions undergoes reaction in disrotatory fashion and polyene containing odd number of bonds undergo reaction in conrotatory fashion.

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Answer 3

Question

Chapter 27, Problem 27.30P

Interpretation Introduction

(a)

Interpretation: The product formed by the thermal electrocyclic ring opening or ring closure to the given compound is to be predicted. The process has to be labeled as conrotatory and disrotatory and the stereochemistry around stereogenic center and double bond is to be indicated.

Concept introduction: Electrocyclic reactions involve ring opening or ring closure in a conjugated polyene. According to Woodward-Hoffmann rules, the polyene containing even number of bonds in photochemical conditions undergoes reaction in disrotatory fashion and polyene containing odd number of bonds undergo reaction in conrotatory fashion.

Interpretation Introduction

(b)

Interpretation: The product formed by the thermal electrocyclic ring opening or ring closure to the given compound is to be predicted. The process has to be labeled as conrotatory and disrotatory and the stereochemistry around stereogenic center and double bond is to be indicated.

Concept introduction: Electrocyclic reactions involve ring opening or ring closure in a conjugated polyene. According to Woodward-Hoffmann rules, the polyene containing even number of bonds in photochemical conditions undergoes reaction in disrotatory fashion and polyene containing odd number of bonds undergo reaction in conrotatory fashion.

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Answer 4

Question

Chapter 27, Problem 27.30P

Interpretation Introduction

(a)

Interpretation: The product formed by the thermal electrocyclic ring opening or ring closure to the given compound is to be predicted. The process has to be labeled as conrotatory and disrotatory and the stereochemistry around stereogenic center and double bond is to be indicated.

Concept introduction: Electrocyclic reactions involve ring opening or ring closure in a conjugated polyene. According to Woodward-Hoffmann rules, the polyene containing even number of bonds in photochemical conditions undergoes reaction in disrotatory fashion and polyene containing odd number of bonds undergo reaction in conrotatory fashion.

Interpretation Introduction

(b)

Interpretation: The product formed by the thermal electrocyclic ring opening or ring closure to the given compound is to be predicted. The process has to be labeled as conrotatory and disrotatory and the stereochemistry around stereogenic center and double bond is to be indicated.

Concept introduction: Electrocyclic reactions involve ring opening or ring closure in a conjugated polyene. According to Woodward-Hoffmann rules, the polyene containing even number of bonds in photochemical conditions undergoes reaction in disrotatory fashion and polyene containing odd number of bonds undergo reaction in conrotatory fashion.

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Answer 5

Chapter 27, Problem 27.30P

Interpretation Introduction

(a)

Interpretation: The product formed by the thermal electrocyclic ring opening or ring closure to the given compound is to be predicted. The process has to be labeled as conrotatory and disrotatory and the stereochemistry around stereogenic center and double bond is to be indicated.

Concept introduction: Electrocyclic reactions involve ring opening or ring closure in a conjugated polyene. According to Woodward-Hoffmann rules, the polyene containing even number of bonds in photochemical conditions undergoes reaction in disrotatory fashion and polyene containing odd number of bonds undergo reaction in conrotatory fashion.

Interpretation Introduction

(b)

Interpretation: The product formed by the thermal electrocyclic ring opening or ring closure to the given compound is to be predicted. The process has to be labeled as conrotatory and disrotatory and the stereochemistry around stereogenic center and double bond is to be indicated.

Concept introduction: Electrocyclic reactions involve ring opening or ring closure in a conjugated polyene. According to Woodward-Hoffmann rules, the polyene containing even number of bonds in photochemical conditions undergoes reaction in disrotatory fashion and polyene containing odd number of bonds undergo reaction in conrotatory fashion.

Answer 6

Chapter 27, Problem 27.30P

Interpretation Introduction

(a)

Interpretation: The product formed by the thermal electrocyclic ring opening or ring closure to the given compound is to be predicted. The process has to be labeled as conrotatory and disrotatory and the stereochemistry around stereogenic center and double bond is to be indicated.

Concept introduction: Electrocyclic reactions involve ring opening or ring closure in a conjugated polyene. According to Woodward-Hoffmann rules, the polyene containing even number of bonds in photochemical conditions undergoes reaction in disrotatory fashion and polyene containing odd number of bonds undergo reaction in conrotatory fashion.

Answer 7

Chapter 27, Problem 27.30P

Interpretation Introduction

(a)

Interpretation: The product formed by the thermal electrocyclic ring opening or ring closure to the given compound is to be predicted. The process has to be labeled as conrotatory and disrotatory and the stereochemistry around stereogenic center and double bond is to be indicated.

Concept introduction: Electrocyclic reactions involve ring opening or ring closure in a conjugated polyene. According to Woodward-Hoffmann rules, the polyene containing even number of bonds in photochemical conditions undergoes reaction in disrotatory fashion and polyene containing odd number of bonds undergo reaction in conrotatory fashion.

Answer 8

Interpretation Introduction

(b)

Interpretation: The product formed by the thermal electrocyclic ring opening or ring closure to the given compound is to be predicted. The process has to be labeled as conrotatory and disrotatory and the stereochemistry around stereogenic center and double bond is to be indicated.

Concept introduction: Electrocyclic reactions involve ring opening or ring closure in a conjugated polyene. According to Woodward-Hoffmann rules, the polyene containing even number of bonds in photochemical conditions undergoes reaction in disrotatory fashion and polyene containing odd number of bonds undergo reaction in conrotatory fashion.

Answer 9

Interpretation Introduction

(b)

Interpretation: The product formed by the thermal electrocyclic ring opening or ring closure to the given compound is to be predicted. The process has to be labeled as conrotatory and disrotatory and the stereochemistry around stereogenic center and double bond is to be indicated.

Concept introduction: Electrocyclic reactions involve ring opening or ring closure in a conjugated polyene. According to Woodward-Hoffmann rules, the polyene containing even number of bonds in photochemical conditions undergoes reaction in disrotatory fashion and polyene containing odd number of bonds undergo reaction in conrotatory fashion.

Answer 10

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Answer 11

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Answer 13

Ch. 27 - Prob. 27.1P Ch. 27 - Problem 27.2 For each molecular orbital in Figure...Ch. 27 - Problem 27.3 (a) Using Figure 27.2 as a guide,...Ch. 27 - Problem 27.4 (a) How many molecular orbitals are...Ch. 27 - Prob. 27.5P Ch. 27 - Prob. 27.6P Ch. 27 - Prob. 27.7P Ch. 27 - Prob. 27.8P Ch. 27 - Prob. 27.9P Ch. 27 - Prob. 27.10P

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Chapter 27 Solutions