Concept explainers
Interpretation:The reason behind excess usage of methyl magnesium iodide andmethyl lithium and number of equivalents of methyl magnesium iodide and methyl lithiumneeded in each case along with the products formed at functionalized sites should be given.
Concept introduction: The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.
Grignard reagents are
Methyl bromide reacts with magnesium ether to give Grignard reagent. This Grignard methyl magnesium bromide on treatment with formaldehyde gives corresponding alcohol. The mechanistic pathway for the latter reaction is as follows:
The polar carbonyl bond breaks and the polar Grignard reagent attack at electron-deficient carbon. Finally with the hydrolysis and work up the alcohol is formed.
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Organic Chemistry: Structure and Function
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- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning