Illicium verum, commonly called Star anise, is a small native evergreen tree grown corresponding car — Organic Chemistry Chemistry Question

Draw the structures for the compounds Y₁ and Y₂ and hence deduce the structure of Y₃ and A, B, C, D, given that in A there is only one ethylenic hydrogen atom.

Anethole, a main component of star anise oil, is an inexpensive chemical precursor for the production of many pharmaceutical drugs.
Treating anethole with sodium nitrite in acetic acid gives a crystalline solid E (C₁₀H₁₀N₂O₃).
The IR spectrum of E shows there is no non-aromatic C=C double bond. The ¹H NMR spectrum of E is given below.

CH^3-C 2.3 ppm 2.6 ppm 2.6 ppm
What differences in the structure between E and anethole can be obtained from the ¹H NMR data? Pick one of the following statements.
i) E contains a cis^-C=C ethylenic bond while that of anethole is trans.
ii) E cannot contain a non-aromatic C=C bond.
iii) E is the adduct of anethole and N₂O₂.

Suggest structures for E, F and G, assuming that they do NOT contain three-membered rings.
A simplified structure for compound E is shown below; the R group does not change throughout the rest of this question.

Compound E is nitrated and subsequently reduced with sodium dithionite to H. Treatment of H with sodium nitrite and hydrochloric acid at 0–5 oC and subsequently reduced with stannous chloride to provide I (R–C₇H₉N₂O). One-pot reaction (three component reaction) of H, benzaldehyde and thioglycolic acid (HSCH₂CO₂H) leads to the formation of J. Reaction of I and methyl phenyl ketone in the presence of ZnCl₂ affords K.
Give the structures for H, I, J and K in the following scheme: