Organic Chemistry (6th Edition)
Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 25.3, Problem 8P
Interpretation Introduction

Interpretation: The structure of provitamin D3 is to be drawn.

Concept introduction: Electrocyclic reactions involve the conversion of σ bonds into π bonds or π bonds into σ bonds. These reactions can take place in photochemical and as well as thermal conditions. The photochemical and thermal reactions take place in the presence of light and heat respectively.

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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Hydrocarbon A has the molecular formula C14H10C12. It absorbs eight molar equivalents of any hydrogen isotope using a Nickel catalyst. When subjected to ozonolysis, Compound A yields oxalic acid and the chiral chloropentane dioic acid. Write the reactions and propose a structure for A.
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Vitamin D3, the most abundant of the D vitamins, is synthesized from 7-dehydrocholesterol, a compound found in milk and fatty fish such as salmon and mackerel. When the skin is exposed to sunlight, a photochemical electrocyclic ring opening forms provitamin D3, which is then converted to vitamin D3 by a sigmatropic rearrangement (Section 27.5). Draw the structure of provitamin D3.
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