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Summary: CHM 2220 Organic Chemistry 2 Winter Term 2007
Problem Set #5 of 5 20 PTS Instructor: Prof. Andreana
Room #: DRY 0146
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1) The N,N-dimethylenamine of isobutyraldehyde and methyl vinyl ketone react to give the
dihydropyran A. When this compound was treated with methylmagnesium iodide, it gave the
ketone B, but when it was treated with phenyllithium, it gave the alcohol C (actually a mixture of two
diastereomers) (I. Fleming, M. H. Karger, J. Chem. Soc.(C), 1965, 226). 4 PTS
Me2N O rt
12 h
+
OMe2N
A 60%
MeMgI
Et2O, rt, 30 min
PhLi
Et2O, 0 C, 2 h
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