Question

Compound A, $\mathrm{C}_{10} \mathrm{H}_{18} \mathrm{O},$ undergoes reaction with dilute $\mathrm{H}_{2} \mathrm{SO}_{4}$ at $50^{\circ} \mathrm{C}$ to yield a mixture of two alkenes, $\mathrm{C}_{10} \mathrm{H}_{16}$. The major alkene product, $\mathrm{B}$. gives only cyclopentanone after ozone treatment followed by reduction with zinc in acetic acid. Identify $\mathbf{A}$ and $\mathbf{B}$, and write the reactions.

Name: Compound A, C10H18O, undergoes reaction with dilute H2SO4 at 50^∘C to yield a mixture of two alkenes, C10H16. The major alkene product, B. gives only cyclopentanone after ozone treatment followed by reduction with zinc in acetic acid. Identify 𝐀 and 𝐁, and write the reactions.
Uploaded: 2024-03-19T15:11:09-08:00
Duration: 1 min 56 s
Channel: Grigoriy Sereda
Description: Compound A, C10H18O, undergoes reaction with dilute H2SO4 at 50^∘C to yield a mixture of two alkenes, C10H16. The major alkene product, B. gives only cyclopentanone after ozone treatment followed by reduction with zinc in acetic acid. Identify 𝐀 and 𝐁, and write the reactions.

          Compound A, $\mathrm{C}_{10} \mathrm{H}_{18} \mathrm{O},$ undergoes reaction with dilute $\mathrm{H}_{2} \mathrm{SO}_{4}$ at $50^{\circ} \mathrm{C}$ to yield a mixture of two alkenes, $\mathrm{C}_{10} \mathrm{H}_{16}$. The major alkene product, $\mathrm{B}$. gives only cyclopentanone after ozone treatment followed by reduction with zinc in acetic acid. Identify $\mathbf{A}$ and $\mathbf{B}$, and write the reactions.

Added by Michelle C.

Organic Chemistry

Janice Gorzynski Smith 4th Edition

Instant Answer

Solved by Expert Grigoriy Sereda

03/19/2024

Step 1

It is an oxygen-containing compound with 10 carbon atoms and 18 hydrogen atoms. One possibility is that it is a cyclic ether with a 5-membered ring, such as 2-methyltetrahydrofuran: $\mathrm{CH_{3}-CH_{2}-CH_{2}-CH(O)-CH_{2}-CH_{2}-CH_{2}-CH_{2}-CH_{3}}$ Show more…

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Compound A, $\mathrm{C}_{10} \mathrm{H}_{18} \mathrm{O},$ undergoes reaction with dilute $\mathrm{H}_{2} \mathrm{SO}_{4}$ at $50^{\circ} \mathrm{C}$ to yield a mixture of two alkenes, $\mathrm{C}_{10} \mathrm{H}_{16}$. The major alkene product, $\mathrm{B}$. gives only cyclopentanone after ozone treatment followed by reduction with zinc in acetic acid. Identify $\mathbf{A}$ and $\mathbf{B}$, and write the reactions.