EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 8220103151757
Author: LOUDON
Publisher: MAC HIGHER
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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.

EBK 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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Compound A has the formula C₂H₁9Cl. B is a C₂H19Br compound. A and B undergo base-promoted E2 elimination to give the same alkene C as the major product as well as different minor products. C reacts with one molar equivalent of hydrogen in the presence of a palladium catalyst to form 2,6-dimethylheptane. Addition of HCI to C yields A as the major product. Propose structures for A and B. • Do not use stereobonds in your answer. • In cases where there is more than one possible structure for each molecule, just give one for each. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu. ● ▾ *%-85 ChemDoodle Qt Jn [F 116
Compound A (C7H11Br) is treated with magnesium in ether to give B (C7H11MgBr), which reacts violently with D2O to give 1-methylcyclohexene with a deuterium atom on the methyl group (C). Reaction of B with acetone (CH3COCH3) followed by hydrolysis gives D (C10H18O). Heating D with concentrated H2 SO4 gives E (C10 H16), which decolorizes two equivalents of Br2 to give F (C10H16 Br4). E undergoes hydrogenation with excess H2 and a Pt catalyst to give isobutylcyclohexane. Determine the structures of compounds A through F, and show your reasoning throughout.
Compound A (C7H11Br) is treated with magnesium in ether to give B (C7H11MgBr) which reacts violently with D2O to give 1-methylcyclohexene with a deuterium atom on the methyl group (C). Reaction of B with acetone (Ch3COCH3) followed by hydrolysis gives D (C10H18O). Heating D with concentrated H2SO4 gives E (C10H16), which reacts with 2 equivalents of Br2 to give F (C10H16Br4). E undergoes hydrogenation with excess H2 and Pt catalyst to give 2-methylpropylcyclohexane. Determine the structures of compounds A through F, and show your reasoning throughout.
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