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They might cyclise to form a four membered ring or

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Unformatted text preview: Nucleophilic Substitution at C=O with Loss of Oxygen PROBLEM 5 In the textbook (p. 228) we say that the Grignard reagent below is ‘an unstable structure – impossible to make.’ Why is this? What would happen if you tried to make it? O O Mg × Br MgBr Purpose of the problem Revision of the danger of mutually destructive functional groups. Suggested solution There are various possibilities that all arise from the presence of a carbonyl group and a Grignard in the same molecule. These two would react together. They might cyclise to form a four- membered ring or a bimolecular reaction might lead to a dimer and perhaps polymerisation. MgBr O O ? O O ? H2O HO O O Br Br BrMg PROBLEM 6 Suggest mechanisms for these reactions. O CHO O H2N + HO NH2 HN CO2Me CO2H O O H N O CH2 O NaCN, NH4Cl CH2 N CN Purpos...
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