Question

Propose syntheses of the following molecules, starting from benzene, toluene or phenol, any inorganic reagents and any organic reagent of TWO carbons or less:

4. Propose syntheses of the following molecules, starting from benzene, toluene or phenol, any inorganic reagents and any organi c reagent of TWO carbons or le a) NO2 b) CO2H c) OH d) e) NO2 NO2 Br CI CI CO2H Br

Answer 1

Drawn below are the detailed synthetic schemes

(a) nitration and then halogenation of benzene.

(b) alkylation of toluene, then halogenation and oxidation.

(c) dialkylation of phenol.

(d) Halogenation and nitration of benzene then alkylation. Diazotization and reduction. Nucleophilic substitution followed by diazotization and substitution with NO2- gives product.

(e) nitration and then halogenation of benzene.

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NO2 NO Cl Fecl (a) HNO CH CH CH COOH Br2 KMno (b) l AICI3 喆li. CH3 COOH 1 Etci AICI3 (c) Br 喆li. Br FeC HNGO Prci NaNO2 HCI Fe/HCI No2 NH2 N^ CI NH NO NaNH2 HCI Br HNO3 H2 SO4 FeC ног NO