Q10(a). Identification of a phenolic propenyl aromatic compound
Identify the compound: M⁺=164; IR 3510, 3030, 2910, 1595, 1430, 1220, 1010 cm⁻¹; three aromatic protons (dd, d, d); vinyl signals 6.35 d and 5.67 dq with J=14.5 Hz; 6.0 s (1H), 3.93 s (3H), 1.87 d (3H); ten ¹³C signals including 55.86 and 18.26 ppm. UV bands shift from 263/300 to 288/315 nm on raising pH.
Answer in brief
The structure is (E)-isoeugenol: 2-methoxy-4-(prop-1-en-1-yl)phenol.
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CoversIdentification of a phenolic propenyl aromatic compoundCombined spectral analysis
All parts of Question 10
- 10(a) Identification of a phenolic propenyl aromatic compound10 marks
- 10(b) Bulky substituents and diene conformation5 marks
- 10(c) Chemoselective epoxidation10 marks
- 10(d) Cyclohexanone mass fragmentation5 marks