Phenyl Grignard reagent adds to 2-methylpropanal to give the secondary alcohol shown
Chapter 13, Problem 13-55(choose chapter or problem)
Phenyl Grignard reagent adds to 2-methylpropanal to give the secondary alcohol shown. The proton NMR of 2-methylpropanal shows the two methyl groups as equivalent (one doublet at d 1.1), yet the product alcohol, a racemic mixture, shows two different 3H doublets, one at d 0.75 and one around d 1.0. MgBr 2-methylpropanal O H + ether H3O+ H OH 1 2 (a) Draw a Newman projection of the product along the C1C2 axis. (b) Explain why the two methyl groups have different NMR chemical shifts. What is the term applied to protons such as these?
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