The Following Compound Was Treated with the Following Sequence of Reagents

question 25

Multiple Choice

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?

• A) C=O stretch
• B) C-O stretch
• C) C=C stretch
• D) C-H stretch
• E) a and b

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