Q65E - Organic Chemistry (Mcmurry)

Question

Compound A, ${\mathbf{C}}_{10}{\mathbf{H}}_{18}\mathbf{O}$ , undergoes reaction with dilute ${\mathbf{H}}_2{\mathbf{SO}}_4$ at $\mathbf{25}\mathbf{°}\mathbf{C}$ to yield a mixture of two alkenes, ${\mathbf{C}}_{10}{\mathbf{H}}_{16}$ . The major alkene product, B, gives only cyclopentanone after ozone treatment followed by reduction with zinc in acetic acid. Write the reactions involved, and identify A and B.

Step-by-Step Solution

Answer

The reactions involved are shown as,

Step 1: Organic reactions

The organic reactions involved major and minor products forming depending upon their yields. For the oxidation of alkene bonds, the oxidizing agents used in organic reactions are ozone, followed by reduction by Zn in acetic acid.

Step 2: The reactions involved and identification of A and B

The compound A with chemical formula ${\text{C}}_{\text{10}}{\text{H}}_{\text{18}}\text{O}$ undergoes reaction with dilute ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ at  ${\text{25}}^{\text{o}}\text{C}$ and yields two types of alkenes, one is major, and the other is minor. The major product (B) further on treatment with ozone followed by reduction with zinc in acetic acid and gives two molecules of cyclopentanone. The reaction is as follows, 

The reactions involved and identification of A and B