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

. (11pts total) Consider the arrows pointing at three different carbon-carbon bonds in the molecule depicted below. Bond B 2°C. +2°C. < cleavage Bond A • CH3 + 26. t cleavage 2°C• +3°C• Bond C Cleavage CH3 ZC '2°C. 26. E Strongest 3°C. 2C. Gund Largest BDE weakest bond In that molecule a. (2pts) Which bond between A-C is weakest? Which is strongest? Place answers in appropriate boxes. Weakest C bond Produces A Weakest Bond Most Strongest Bond Stable radical Strongest Gund produces least stable radicals b. (4pts) Consider the relative stability of all cleavage products that form when bonds A, B, AND C are homolytically cleaved/broken. Hint: cleavage products of bonds A, B, and C are all carbon radicals. i. Which ONE cleavage product is the most stable? A condensed or bond line representation is fine. 人 8°C. formed in bound C cleavage ii. Which ONE cleavage product is the least stable? A condensed or bond line representation is fine. methyl radical •CH3 formed in bund A Cleavage

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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. (11pts total) Consider the arrows pointing at three different carbon-carbon bonds in the molecule depicted below. Bond B 2°C. +2°C. < cleavage Bond A • CH3 + 26. t cleavage 2°C• +3°C• Bond C Cleavage CH3 ZC '2°C. 26. E Strongest 3°C. 2C. Gund Largest BDE weakest bond In that molecule a. (2pts) Which bond between A-C is weakest? Which is strongest? Place answers in appropriate boxes. Weakest C bond Produces A Weakest Bond Most Strongest Bond Stable radical Strongest Gund produces least stable radicals b. (4pts) Consider the relative stability of all cleavage products that form when bonds A, B, AND C are homolytically cleaved/broken. Hint: cleavage products of bonds A, B, and C are all carbon radicals. i. Which ONE cleavage product is the most stable? A condensed or bond line representation is fine. 人 8°C. formed in bound C cleavage ii. Which ONE cleavage product is the least stable? A condensed or bond line representation is fine. methyl radical •CH3 formed in bund A Cleavage

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