Compound A, C 10 H 18 O, when warmed with dilute H 2 SO 4 at 50 o C yields a mixture of two alkenes , C 10 H 16 . The major alkene product, B, gives only cyclopentanone upon ozonolysis followed by reduction with zinc in acetic acid. Compounds A and B are to be identified and the reactions are to be written. Concept introduction: Alcohols gets dehydrated to yield alkenes when warmed with dilute H 2 SO 4 at 50 o C. Symmetrical alkenes upon ozonolysis followed by reduction with zinc in acetic acid will yield only a single product. If the doubly bonded carbons are attached to two substituents then upon ozonolysis a ketone is produced. To identify: The compounds A and B based on the reactions given and to explain the reactions.

Question

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

Answer 1

Question

Chapter 8.SE, Problem 61AP

Interpretation Introduction

Interpretation:

Compound A, C₁₀H₁₈O, when warmed with dilute H₂SO₄ at 50^oC yields a mixture of two alkenes, C₁₀H₁₆. The major alkene product, B, gives only cyclopentanone upon ozonolysis followed by reduction with zinc in acetic acid. Compounds A and B are to be identified and the reactions are to be written.

Concept introduction:

Alcohols gets dehydrated to yield alkenes when warmed with dilute H₂SO₄ at 50^oC. Symmetrical alkenes upon ozonolysis followed by reduction with zinc in acetic acid will yield only a single product. If the doubly bonded carbons are attached to two substituents then upon ozonolysis a ketone is produced.

To identify:

The compounds A and B based on the reactions given and to explain the reactions.

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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

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