Question

What is the major Organic product of the following sequence of reactions? CH AH 1) CHZI (excess) H H 2) Ag20. HOA Ĩ NH CH CH CH ΠΗ H H 1 H H H H H ST H NH CH; (b) CH AH CH; CH; JAH H H H 0 H H "CH; (f) (d) (c)

Answer 1

1 ) CHg Н 1) CH>I (excess) 27 A920, H20,4 H I luus. NH2 Primary amines on reaction with excess with excess alkyl halide give quarternary amines, which on reaction with silveroxide (Ag, 0) undergo Hofmann elimination to Proint given al kene . Mechanism lol CH3 19.00 H CH₃ Tul JE EHz-1 NH₂ H H دزد ۱ NH +5 s -> City Base HE W H2no H9 B+ (Nano 14 wania CH₂ H 4 us Hlustong N-CH₂ It CH2 r.1) t (xcess Similer mechanism CH₃ Ilu N (CH3), I CS Scanned with CamScanner

10 Step-2 Agrego Ag - 0 : Do -Agd + H 2. - Agolt H OOH The Hofmann eliminination is an anti elemination. This elimination reachich of alkyl trimethyl amines proceeds with anti Stereochemistry..) In anri elimination the base attacks the ß-hydrogen on the opposite side of the Leaving group. CH3 eltz 4 H >H Anti eimination ม Gm Celtag -NCH3), H CH₃ OH Anse H O-CH3 2 HU نیم ۲ 14 lo o- CH3 nel stup o CH3 + that +CI- oxonium jon CS Scanned with CamScanner

Step- Elci GA CH3 :OH + CH3cd 1 Miricorren! Aus- a 0-11 + cll34 ) (...((ان OW H3p²4 LIVADA wis protonation of alcone step-) Ho-Hapog OH + HOW Step-2 wator diparts Leaving group forming Carbocation. CA -H2o Tertiary Carb-Carian ViY stanie The more substituted alkene is the stable produit (major produkt) CS

yag Ho-pogitz (major product Yy (minor produb) @ Ans Major Produitis CS Scanned with CamScanner