Organic Chemistry (6th Edition)
Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
Question
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Chapter 25.5, Problem 18P
Interpretation Introduction

(a)

Interpretation: The product formed from the [1,7] sigmatropic rearrangement of deuterium in the given triene is to be identified.

Concept introduction: Sigmatropic rearrangements are pericyclic reactions which involve the migration of sigma bonds. In these reactions, old sigma bonds are broken and new sigma bonds are formed.

Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.

Interpretation Introduction

(b)

Interpretation: If the given reaction proceeds in a suprafacial or antarafacial manner under thermal conditions is to be predicted.

Concept introduction: Sigmatropic rearrangements are pericyclic reactions which involve the migration of sigma bonds. In these reactions, old sigma bonds are broken and new sigma bonds are formed.

Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.

Interpretation Introduction

(c)

Interpretation: If the given reaction proceeds in a suprafacial or antarafacial manner under photochemical conditions is to be predicted.

Concept introduction: Sigmatropic rearrangements are pericyclic reactions which involve the migration of sigma bonds. In these reactions, old sigma bonds are broken and new sigma bonds are formed.

Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.

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(a) What product is formed when triene N undergoes thermal electrocyclic ring closure? (b) What product is formed when triene N undergoes photochemical ring closure? (c) Label each process as conrotatory or disrotatory.
(a) What product is formed when triene N undergoes thermal electrocyclic ring closure? (b)What product is formed when triene N undergoes photochemical ring closure? (c) Label each process as conrotatory or disrotatory.
(a) What product(s) are formed when the E isomer of C6H5CH = CHC6H5 is treated with Br2, followed by one equivalent of KOH? Label the resulting alkene(s) as E or Z. (b) What product(s) are formed when the Z isomer of C6H5CH = CHC6H5 is subjected to the same reaction sequence? (c) How are the compounds in parts (a) and (b) related to each other?
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