Organic 2 Review Problem 260

Organic 2 Review Problem 260 - 244 P RACTICAL ORGANIC...

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

View Full Document Right Arrow Icon
244 PRACTICAL ORGANIC CHEMISTRY Thus phenol when subjected to the Schotten-Baumann reaction first dis- solves in the sodium hydroxide to give sodium phenoxide, which then undergoes C 6 H 5 COCl + NaOC 6 H 5 -> C 6 H 5 COOC 6 H 5 + XaCl bcnzoylation to give phenyl benzoate. An aqueous suspension of aniline similarly gives benzoyl-aniline, or phenyl-benzamide (frequently called benz- C 6 H 5 NHH + ClCOC 6 H 5 -> C 6 H 5 NHCOC 6 H 5 -f HCl anilide); whilst monomethylaniline gives benzoyl-monomethylaniline or C 6 H 5 N(CH 3 )H -f ClCOC 6 H 3 -> C 6 H 5 X(CH 3 )COC 6 H 5 + HCl A 7 -methylphenylbenzamide. Tertiary amines clearly cannot react in this way. When these benzoyl compounds separate in the course of the Schotten- Baumann reaction, they frequently occlude traces of unchanged benzoyl chloride, which thus escapes hydrolysis by the alkali: it is advantageous there- fore to recrystallise the benzoyl compounds whenever possible from ethanol or methylated spirit, since these solvents will esterify the unchanged chloride
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

This note was uploaded on 09/19/2011 for the course CHM 2211 taught by Professor Castalleano during the Fall '06 term at University of Florida.

Ask a homework question - tutors are online