a) Interpretation: The structure of the alkene that yields (CH 3 ) 2 C=O + H 2 C=O as products when treated with ozone followed by treatment with Zn is to be given. Concept introduction: Ozone adds to the double bond in alkenes to produce compounds called ozonides. The ozonides upon immediate treatment with Zn and acetic acid yield carbonyl compounds. Each carbon in the double bond cleaved gets attached to an oxygen atom. Hence the carbons that contain oxygen atom in the products are bonded through a double bond in the alkene. To give: The structure of the alkene that yields (CH 3 ) 2 C=O + H 2 C=O as products when treated with ozone followed by treatment with Zn.

Question

What would be the reagents and conditions above and below the arrow that will complete the proposed acetoacetic ester synthesis? If it cannot be done efficiently, then I will choose that answer. There could be 2 or 4 reagents involved. Please provide a detailed explanation and drawings showing how it would proceed with the correct reagents.

Answer 1

Question

Chapter 8.8, Problem 16P

Interpretation Introduction

a)

Interpretation:

The structure of the alkene that yields (CH₃)₂C=O + H₂C=O as products when treated with ozone followed by treatment with Zn is to be given.

Concept introduction:

Ozone adds to the double bond in alkenes to produce compounds called ozonides. The ozonides upon immediate treatment with Zn and acetic acid yield carbonyl compounds. Each carbon in the double bond cleaved gets attached to an oxygen atom. Hence the carbons that contain oxygen atom in the products are bonded through a double bond in the alkene.

To give:

The structure of the alkene that yields (CH₃)₂C=O + H₂C=O as products when treated with ozone followed by treatment with Zn.

Interpretation Introduction

b)

Interpretation:

The structure of the alkene that yields 2 equivalents of CH₃CH₂CH=O as products when treated with ozone followed by treatment with Zn is to be given.

Concept introduction:

Ozone adds to the double bond in alkenes to produce compounds called ozonides. The ozonides upon immediate treatment with Zn and acetic acid yield carbonyl compounds. Each carbon in the double bond cleaved gets attached to an oxygen atom. Hence the alkene should contain the carbons that contain oxygen atom in the products in a doubly bond.

To give:

The structure of the alkene that yields 2 equivalents of CH₃CH₂CH=O as products when treated with ozone followed by treatment with Zn.

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