Dolbier HW Solutions 539

Dolbier HW Solutions 539 - 633 AMINES (h) Acetanilide is a...

Info iconThis preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
( h ) Acetanilide is a reactive substrate toward electrophilic aromatic substitution. On reaction with chloroacetyl chloride, it undergoes Friedel Crafts acylation, primarily at its para position. Acylation, rather than alkylation, occurs. Acyl chlorides are more reactive than alkyl chlorides toward electrophilic aromatic substitution reactions as a result of the more stable intermediate (acylium ion) formed. ( i ) Reduction with iron in hydrochloric acid is one of the most common methods for converting nitroarenes to arylamines. ( j ) Primary arylamines are converted to aryl diazonium salts on treatment with sodium nitrite in aqueous acid. When the aqueous acidic solution containing the diazonium salt is heated, a phenol is formed. ( k ) This problem illustrates the conversion of an arylamine to an aryl chloride by the Sandmeyer reaction. ( l ) Diazotization of primary arylamines followed by treatment with copper(I) bromide converts
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.
Ask a homework question - tutors are online