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Dolbier HW Solutions 531

Dolbier HW Solutions 531 - 625 AMINES(b In this example one...

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( b ) In this example one bromine is attached to a primary and the other to a secondary carbon. Phthalimide anion is a good nucleophile and reacts with alkyl halides by the S N 2 mechanism. It attacks the less hindered primary carbon. ( c ) Both bromines are bonded to primary carbons, but branching at the adjacent carbon hinders nucleophilic attack at one of them. 22.31 ( a ) Amines are basic and are protonated by hydrogen halides. ( b ) Equimolar amounts of benzylamine and sulfuric acid yield benzylammonium hydrogen sulfate as the product. ( c ) Acetic acid transfers a proton to benzylamine. Benzylamine Acetic acid Benzylammonium acetate C 6 H 5 CH 2 NH 2 1 CH 3 COH O C 6 H 5
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