Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 24, Problem 24.32P
Interpretation Introduction

Interpretation:

The structure of R has to be given and the synthesis of Exaltolide has to be given from the starting material.

Concept Introduction:

Alkene metathesis:

An organometallic catalyzed reaction in which two alkenes exchange carbon atoms of their double bonds are said to be Alkene metathesis reaction.  Two alkenes are in same molecule and the product is a cycloalkene and ring closing occurs.  The catalyst used is Ru‑nucleophilic carbene complex.

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Organic Chemistry, Chapter 24, Problem 24.32P

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1. The molecular formula of an unknown compound A is C7H14. On ozonolysis, A gave two products B and C where both reacted with 2,4-dinitrophenylhydrazine to give solid derivatives. Compound B gave positive results to both Tollens’ and iodoform tests, while C gave negative results to both of the tests. What is the structural formula of A, B and C. Explain your answer.       2. Compound P, C4H9Br reacts with aqueous solution of sodium hydroxide to form compound Q, C4H10O. Compound Q decolourised acidified solution of potassium permanganate to yield compound R, C4H8O which give an orange precipitate when react with 2,4- dinitrophenylhydrazine. Both compounds Q and R formed yellow precipitate with alkaline iodine solution. Compound P also reacts with magnesium metal to form compound S, C4H9MgBr. Compound R reacts with compound S, followed by hydrolysis to give compound T, C8H18O. Compound T gives off white fumes when react with PCl5. (a) Determine the structural formulae of P, Q, R, S and…
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