(a) Interpretation: The product of given electrocyclic reaction is to be drawn. 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 thermal conditions undergoes reaction in conrotatory fashion and polyene containing odd number of bonds undergo reaction in disrotatory fashion.

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Answer 1

Question

Chapter 27, Problem 27.33P

Interpretation Introduction

(a)

Interpretation: The product of given electrocyclic reaction is to be drawn.

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 thermal conditions undergoes reaction in conrotatory fashion and polyene containing odd number of bonds undergo reaction in disrotatory fashion.

Interpretation Introduction

(b)

Interpretation: The product of given electrocyclic reaction is to be drawn.

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

(c)

Interpretation: The product of given electrocyclic reaction is to be drawn.

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 thermal conditions undergoes reaction in conrotatory fashion and polyene containing odd number of bonds undergo reaction in disrotatory fashion.

Interpretation Introduction

(d)

Interpretation: The product of given electrocyclic reaction is to be drawn.

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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Draw the product of each electrocyclic reaction.a. the thermal electrocyclic ring closure of (2E,4Z,6Z)-nona-2,4,6-trieneb. the photochemical electrocyclic ring closure of (2E,4Z,6Z)-nona-2,4,6-trienec. the thermal electrocyclic ring opening of cis-5-ethyl-6-methylcyclohexa-1,3-diened. the photochemical electrocyclic ring opening of trans-5-ethyl-6-methylcyclohexa-1,3- diene

best condition for the reaction (1r,2s)-1 bromo-2methylcyclohexane->(s)3-methylcyclohex-1ene

A student adds NBS to a solution of 1-methylcyclohexene and irradiates the mixture with a sunlamp until all the NBS has reacted. After a careful distillation, the product mixture contains two major products of formula C7H11Br. (a)Rank these three intermediates from most stable to least stable.

Answer 2

Question

Chapter 27, Problem 27.33P

Interpretation Introduction

(a)

Interpretation: The product of given electrocyclic reaction is to be drawn.

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 thermal conditions undergoes reaction in conrotatory fashion and polyene containing odd number of bonds undergo reaction in disrotatory fashion.

Interpretation Introduction

(b)

Interpretation: The product of given electrocyclic reaction is to be drawn.

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

(c)

Interpretation: The product of given electrocyclic reaction is to be drawn.

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 thermal conditions undergoes reaction in conrotatory fashion and polyene containing odd number of bonds undergo reaction in disrotatory fashion.

Interpretation Introduction

(d)

Interpretation: The product of given electrocyclic reaction is to be drawn.

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 27.33P

Interpretation Introduction

(a)

Interpretation: The product of given electrocyclic reaction is to be drawn.

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 thermal conditions undergoes reaction in conrotatory fashion and polyene containing odd number of bonds undergo reaction in disrotatory fashion.

Interpretation Introduction

(b)

Interpretation: The product of given electrocyclic reaction is to be drawn.

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

(c)

Interpretation: The product of given electrocyclic reaction is to be drawn.

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 thermal conditions undergoes reaction in conrotatory fashion and polyene containing odd number of bonds undergo reaction in disrotatory fashion.

Interpretation Introduction

(d)

Interpretation: The product of given electrocyclic reaction is to be drawn.

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 27.33P

Interpretation Introduction

(a)

Interpretation: The product of given electrocyclic reaction is to be drawn.

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 thermal conditions undergoes reaction in conrotatory fashion and polyene containing odd number of bonds undergo reaction in disrotatory fashion.

Interpretation Introduction

(b)

Interpretation: The product of given electrocyclic reaction is to be drawn.

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

(c)

Interpretation: The product of given electrocyclic reaction is to be drawn.

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 thermal conditions undergoes reaction in conrotatory fashion and polyene containing odd number of bonds undergo reaction in disrotatory fashion.

Interpretation Introduction

(d)

Interpretation: The product of given electrocyclic reaction is to be drawn.

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 27.33P

Interpretation Introduction

(a)

Interpretation: The product of given electrocyclic reaction is to be drawn.

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 thermal conditions undergoes reaction in conrotatory fashion and polyene containing odd number of bonds undergo reaction in disrotatory fashion.

Interpretation Introduction

(b)

Interpretation: The product of given electrocyclic reaction is to be drawn.

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

(c)

Interpretation: The product of given electrocyclic reaction is to be drawn.

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 thermal conditions undergoes reaction in conrotatory fashion and polyene containing odd number of bonds undergo reaction in disrotatory fashion.

Interpretation Introduction

(d)

Interpretation: The product of given electrocyclic reaction is to be drawn.

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 27.33P

Interpretation Introduction

(a)

Interpretation: The product of given electrocyclic reaction is to be drawn.

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 thermal conditions undergoes reaction in conrotatory fashion and polyene containing odd number of bonds undergo reaction in disrotatory fashion.

Answer 7

Chapter 27, Problem 27.33P

Interpretation Introduction

(a)

Interpretation: The product of given electrocyclic reaction is to be drawn.

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 thermal conditions undergoes reaction in conrotatory fashion and polyene containing odd number of bonds undergo reaction in disrotatory fashion.

Answer 8

Interpretation Introduction

(b)

Interpretation: The product of given electrocyclic reaction is to be drawn.

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 of given electrocyclic reaction is to be drawn.

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

Interpretation Introduction

(c)

Interpretation: The product of given electrocyclic reaction is to be drawn.

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 thermal conditions undergoes reaction in conrotatory fashion and polyene containing odd number of bonds undergo reaction in disrotatory fashion.

Answer 11

Interpretation Introduction

(c)

Interpretation: The product of given electrocyclic reaction is to be drawn.

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 thermal conditions undergoes reaction in conrotatory fashion and polyene containing odd number of bonds undergo reaction in disrotatory fashion.

Answer 12

Interpretation Introduction

(d)

Interpretation: The product of given electrocyclic reaction is to be drawn.

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 13

Interpretation Introduction

(d)

Interpretation: The product of given electrocyclic reaction is to be drawn.

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 14

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Answer 15

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Answer 16

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Answer 17

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 how the photochemical electrocyclic ring closure of (2E,4Z,6Z)-nona-2, 4, 6-triene is shown in Figure 1.

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Chapter 27 Solutions