Question

2. Synthesize the following amide ci' Retrosynthetic Analysis Synthesis

Answer 1

Retrosynthetic analysis:

IZ IZ C2 ERO u (g) (chlorination) -NH₂ + Eto I Sn/Ha (Reduction) N HNO₃ ALC H 2- 2 (chlorination) (e) (Nitration)

From the retrosynthetic analysis, we can see that the final product (g) can be prepared by chlorination of compound-(f). Compound-(f) can be prepared by the reaction of compound-(d) and compound-(e). Compound-(d) can be prepared by reduction of compound-(c). Compound-(c) can be prepared by chlorination of compound-(b). And compound-(b) can be prepared by nitration of benzene or compound-(a).

Synthesis: (following is the complete synthesis with mechanism)

H foJ -204⑤N onuno One。 tNO2

a-i Ala, + NON uerto ea, NO₂ HNO dem JO > H₂SO4 (Nitration) (a) os=3| Uz (chlordnation) nec, 5-OH Noz NUZ. Sn/ha pene ( Reduction) Eto le) OL IZ NOEt ZI HK 11 Ala, Chlorination caracas & 1- Ала IZ (9)

Some explanation of chlorination positions:

Chlorination of compound-b to compound-c:

(Electron withdrawing group activates meta-positions for chlorination) & Meta position

Chlorination of compound-f to compound-g:

oretho IZ Electron donating activates orath & for chlorcination. group parca - positrons ontho para IZ (Bulky group storically hindores the orathopositions from chlorination) 2 parca-position is free, so chlorination occurs at para position.