The following compound
was treated with the following sequence of reagents
1. HBr, H₂O₂
2. Li, ether
3. Formaldehyde, followed by H₃O⁺
4. CrO₃, pyridine
5. Ph₃P=CH₂
Which of the following absorptions would you not expect to see in the IR spectrum of the final product of this multistep synthesis?

Question

The following compound

was treated with the following sequence of reagents
1. HBr, H₂O₂
2. Li, ether
3. Formaldehyde, followed by H₃O⁺
4. CrO₃, pyridine
5. Ph₃P=CH₂
Which of the following absorptions would you not expect to see in the IR spectrum of the final product of this multistep synthesis?

Quizplus · Accepted Answer

The HBr used in the first step would cleave any O-H bonds to form an alcohol. The Li/ether combination used in the second step is a reducing agent and would convert any carbonyl groups (C=O) to alcohols (C-O). Therefore, we would not expect to see a C=O stretch or a C-O stretch in the final product.

The Following Compound Was Treated with the Following Sequence of Reagents