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38 CHAPTER 2 
 
the original carbon-nitrogen  bond can become a lone 
pair on a different carbon atom. 
 
 
(b) Two curved arrows are required to convert resonance 
structure 2a to resonance structure 2c. One arrow shows 
that the lone pair on carbon can become a carbon-carbon 
 bond while the other arrow shows that the electrons in 
the carbon-oxygen  bond can become a third lone pair 
on oxygen. 
 
 
 
2.18. 
(a) This pattern (lone pair next to a  bond) has two 
curved arrows. The first curved arrow is drawn showing 
a lone pair becoming a  bond, while the second curved 
arrow shows a  bond becoming a lone pair: 
 
O
O
O
O
 
 
(b) This pattern (lone pair next to a  bond) has two 
curved arrows. The first curved arrow is drawn showing 
a lone pair becoming a  bond, while the second curved 
arrow shows a  bond becoming a lone pair: 
 
 
 
(c) This pattern (lone pair next to a  bond) has two 
curved arrows. The first curved arrow is drawn showing 
a lone pair becoming a  bond, while the second curved 
arrow shows a  bond becoming a lone pair: 
 
 
 
(d) This pattern (lone pair next to a  bond) has two 
curved arrows. The first curved arrow is drawn showing 
a lone pair becoming a  bond, while the second curved 
arrow shows a  bond becoming a lone pair: 
 
 
(e) This pattern (lone pair next to a  bond) has two 
curved arrows. The first curved arrow is drawn showing 
a lone pair becoming a  bond, while the second curved 
arrow shows a  bond becoming a lone pair: 
 
 
 
(f) This pattern (lone pair next to a  bond) has two 
curved arrows. The first curved arrow is drawn showing 
a lone pair becoming a  bond, while the second curved 
arrow shows a  bond becoming a lone pair: 
 
 
 
(g) This pattern (lone pair next to a  bond) has two 
curved arrows. The first curved arrow is drawn showing 
a lone pair becoming a  bond, while the second curved 
arrow shows a  bond becoming a lone pair: 
 
 
 
(h) This pattern (lone pair next to a  bond) has two 
curved arrows. The first curved arrow is drawn showing 
a lone pair becoming a  bond, while the second curved 
arrow shows a  bond becoming a lone pair: 
 
 
 
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