suggest a reason for acid chlorides being better acylating reagents than anhydrides?

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suggest a reason for acid chlorides being better acylating reagents than anhydrides?

2006-11-01 20:35:29 · 2 answers · asked by U2 1 in Science & Mathematics ➔ Chemistry

2 answers

hmmm... acid chlorides can easily react with AlCl3 to form RCO+ that will serve as the electrophile during acylation.

acid anhydrides may have the difficulty in forming the electrophile because of its O=C--O--C=O system where electrons can freely move around. in effect, site of nucleophilic attack for AlCl3 becomes weak - weaker than that of acid chlorides.

2006-11-01 21:28:06 · answer #1 · answered by titanium007 4 · 0⤊ 0⤋

they're more reactive. that's why they make great keytones with organocuprate reagents.

2006-11-02 10:55:13 · answer #2 · answered by shiara_blade 6 · 0⤊ 0⤋