Question

Calibri Light 20 B IC A 2. Provide the structure of all intermediates and all products 1-14. 1. NOCH 2.H.O. COM acid catalyst hint: - BUOH 2 Nai 3, H49 heat 1.(CH,,Culi.cther 2. H,09 1. NOCH 1.HO uinti Page 1 of 4

Answer 1

NaOCH, HO OH OH H+ BuOH carboxylic acid reacts with alchol in presence of acid catalyst, gives ester. Ester alkoxide reacts with gives methyl ester via transesterification NaOH, H2O heat (CH3)2 Culi H20* Aldehyde gives conjugated carbonyl via aldol condensetion. Conjugated carbonyl udergoes 1,4 addition by Gilman's reagent ها NaOCH3 H307 heat Br Br Br First, nucleophilic substitution of alkyl halide. Then, hydrolysis and decarboxylation takesplace NH, PCC OH NaBH3CN NH PCC oxidation of alcohol gives ketone. Ketone reaction with amine followed by reaction with NaNBH3CN gives 20 amine Br BI 312 4 NaOH H20* LiAIH4 H30* OH OH lodoform reaction of ketone gives acid. Carboxylic acid on reduction with LiAlH4 gives alcohol 2 eq. (CH3)2NH LIAIH H20* Acid chloride gives amide when reacted with amine. Amide on reduction gives amine H20+ ☆ CH3MgBr H30+ OH Ketal on deprotection or treating with H30+ gives ketone. Ketone on reaction with Grignard reagent gives 30 alcohol