(a) Interpretation: The product formed by the photochemical 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

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Chapter 27, Problem 27.31P

Interpretation Introduction

(a)

Interpretation: The product formed by the photochemical 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 photochemical 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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Part II. xiao isolated a compound TAD (Ca H 10 N₂) from tobacco and obtained its IR spectrum. Xiao proposed a chemical structure shown below: % Transmittance 4000 3500 3000 2500 2000 Wavenumber (cm-1) 1500 1000 (a) Explain why her proposed structure is inconsistent with the IR spectrum obtained (b) TAD exists as a tautomer of the structure xiao proposed. Draw the structure and explain why it is more compatible with the obtained spectrum. (C) what is the possible source for the fairly intense signal at 1621cm1

AE>AE₁ (Y/N) AE=AE₁ (Y/N) AE

Treatment of 2-phenylpropan-2-amine with methyl 2,4-dibromobutanoate in the presence of a nonnucleophilic base, R3N, involves two successive SN2 reactions and gives compound A. ? NH2 Br Br Propose a structural formula for compound A. You do not have to explicitly draw H atoms. You do not have to consider stereochemistry. In cases where there is more than one answer, just draw one. R3N C14H19NO2 + 2 R3NH*Br A

Answer 2

Question

Chapter 27, Problem 27.31P

Interpretation Introduction

(a)

Interpretation: The product formed by the photochemical 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 photochemical 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 27.31P

Interpretation Introduction

(a)

Interpretation: The product formed by the photochemical 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 photochemical 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 27.31P

Interpretation Introduction

(a)

Interpretation: The product formed by the photochemical 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 photochemical 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 27.31P

Interpretation Introduction

(a)

Interpretation: The product formed by the photochemical 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 photochemical 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 27.31P

Interpretation Introduction

(a)

Interpretation: The product formed by the photochemical 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 27.31P

Interpretation Introduction

(a)

Interpretation: The product formed by the photochemical 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 photochemical 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 photochemical 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 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

Solution Summary: The author explains the process of photochemical electrocyclic ring opening, which is conrotatory, and the stereochemistry around stereogenic center and double bond.

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Chapter 27 Solutions