Consider the following reaction of benzene. [figure] In compound (Q), the percentage of oxygen is %. (Nearest integer)
Answer
10
Solution
Step 1 (Friedel–Crafts acylation): the acyl chloride end (-COCl) acylates benzene in the presence of anhydrous AlCl3, giving P (1-phenylpentane-1,4-dione), C6H5COCH2CH2COCH3.
Step 2 (intramolecular aldol condensation): P is a 1,4-diketone. With aq NaOH the carbanion formed at the terminal CH3 attacks the C=O carbon attached to the ring, giving a five-membered ring; on heating, the aldol loses H2O to give a conjugated enone.
[figure]
Q = 3-phenylcyclopent-2-en-1-one, C11H10O
Molar mass = 11(12) + 10(1) + 16 = 158 g mol-1
\% O = 16158 100 = 10.13\% 10
Answer: 10