Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
Question
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Chapter D, Problem 1PP
Interpretation Introduction

Interpretation:

The product of photochemical cyclization reaction of cis,trans2,4hexadiene is to be determined with the help of given structure.

Concept Introduction:

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The compounds that have the same molecular formula of atoms but the structure of the compounds are different for the positions of atoms are called isomers.

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In double bond or cyclic compounds, if two same functional groups are present on the same side of the double bond or cyclic compound, the given compound can be labeled as cis.

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If the two functional groups are present on the different sides of the double bond or cyclic compound, the given compound can be labeled as Trans.

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Cis-trans isomerism exists in the compounds in which similar groups are present on the adjacent carbon atoms.

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The thermal electrocyclic reaction having 4Π electron takes place with conrotatory motion.

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The photochemical electrocyclic reaction having 4Π electron takes place with disrotatory motion.

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The electrocyclic reactions are initiated by heat or light and are stereospecific in nature.

Expert Solution & Answer
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Answer to Problem 1PP

Solution:

The product of the reaction is given below:

Organic Chemistry, Chapter D, Problem 1PP , additional homework tip  1

Explanation of Solution

The compound cis,trans2,4hexadiene follows 4Π electron rule and according to Woodward-Hoffmann rule, for electrocyclic reaction, the photochemical cyclization reaction of cis,trans2,4hexadiene takes place with disrotatory motion.

Thus, the photochemical cyclization reaction of cis,trans2,4hexadiene is as:

Organic Chemistry, Chapter D, Problem 1PP , additional homework tip  2

Conclusion

The product of the reaction is trans3,4dimethylcyclobutene.

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