CHEM 2262 Chapter : Chapter 17-2262

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15 Mar 2019
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Carbonyl compounds can be classified into two groups. Class i carbonyl compounds are those in which the carbonyl carbon is attached to a group that can be replaced by a nucleophile. Class i carbonyl compounds include carboxylic acids and a group of compounds collectively known as carboxylic acid derivatives. Nitriles are compounds that contain a c n functional group. They are classified as carboxylic acid derivatives because they react with water (in the presence of an acid of base catalyst) to form carboxylic acids. We will see that class i compounds can undergo nucleophilic substitution reactions, but not by the sn1 or sn2 mechanisms that we discussed in the first semester. Class i carbonyl compounds undergo nucleophilic substitution by a two stage, addition-elimination mechanism (which bears some resemblance to the addition-elimination mechanism we discussed for nucleophilic aromatic substitution in chapter 16).

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