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problem2.pdf
Problem Set 2 5.13 Due February 21, 2003 1PM
1. Compound A is reacted in anhydrous diethylether with Mg to give an intermediate
that when reacted with compound B produces C after aqueous workup. What are A, B,
and C. Explain how you arrived at your answer.
MS and 1H- NMR of A
M+
1
IR, 1H-NMR, MS of C (Signal at 2.1 ppm disappears upon D O treatment)
2
6H
3H
1H 2H
M+
2
2. Compound A when treated with H SO (small amount of H O) gives compound B.
2 4 2
Provide the structures of A and B. Explain how you arrived at your answer.
1H-NMR and MS of A
M+
3
1H-NMR, IR and MS of B
3H
3H
2H
M+
4
3. Compound A (F.W.=94.9, 1H-NMR singlet at 2.68ppm) is reacted with
Triphenylphosphine to give compound B. Compound B is reacted with n-butyl lithium to
give an intermediate that when reacted with compound C gives compound D. What are
the compounds A, B, C, and D. Explain how you arri
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