Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 28, Problem 28.40AP
Interpretation Introduction

Interpretation:

When 1, 3, 5-cyclooctatriene, A, is heated to 80-100 °C, it comes to equilibrium with an isomeric compound B.Treatment of the mixture of A and B with CH3O2C-CC-CO2CH3 gives a compound C, which, when heated to 200 °C for 20 minutes, gives dimethyl phthalate and cyclobutene. The compounds B and C, is to be stated and the reactions have occurred is to be explained.

Organic Chemistry, Chapter 28, Problem 28.40AP

Concept introduction:

Commonly, cycloaddition reaction can be referred as a reaction of two different π-electron systems to form a ring product. Notably, in this reaction two new sigma bonds are formed in product with the disappearance of two fewer π-bonds. In other words, cyclo addition reaction can be best described as the reaction of number of electrons involved. In [4+2] cycloaddition one component is having four electrons and other component is having two electrons.

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The reaction of 3,4-dimethyl-3-hexanol (3,4-dimethylhexan-3-ol) with HBr generates compound A as the major product. Treatment of compound A with a strong base gives two isomers of compound B as the major product, along with one isomer of compound C and one isomer of compound D as minor products, all of which have one double-bond equivalent. Identify compounds A, B, C, and D and give their names. By what mechanism does the reaction of 3,4-dimethyl-3-hexanol with HBr occur? By what mechanism does the reaction of A with strong base to form B occur? Propose reaction conditions for an alternative, one-step method for converting 3,4-dimethyl-3-hexanol directly to compound B.
Treatment of a hydrocarbon A (molecular formula C9H18) with Br2 in the presence of light forms alkyl halides B and C, both having molecular formula C9H17Br. Reaction of either B or C with KOC(CH3)3 forms compound D (C9H16) as the major product. Ozonolysis of D forms cyclohexanone and acetone. Identify the structures of A–D.
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