What is an appropriate stepwise synthesis for the following synthesis that uses 1-propanol as the only source of carbon and any other reagents as needed?
◦ 1-propanol reacts with PCC/CH
2Cl
2 to yield an intermediate that reacts with LDA to yield intermediate X, which has a resonance form Y. 1-propanol also reacts with PCl
3 to yield an intermediate Z that reacts with intermediate X, which undergoes the following series of reactions to yield the product: 1. Na
2Cr
2O
7/H
2SO
4/H
2O; 2. Excess CH
3CH
2CH
2OH/H
2SO
4.
◦ 1-propanol reacts with PCC/CH
2Cl
2, then the product reacts with LDA to produce intermediate X, which has resonance forms. 1-propanol reacts with PCl
3, then the product reacts with intermediate X to yield intermediate Y. Intermediate Y reacts with NaBH
4/CH
3OH to yield the product.
◦ 1-propanol reacts with PCl
3 to yield intermediate X. 1-propanol also undergoes the following reaction sequence: 1. Na
2Cr
2O
7/H
2SO
4/H
2O; 2. excess CH
3CH
2CH
2OH/H
2SO
4; 3. LDA; 4. Intermediate X. This yields the product.
◦ A or B
◦ B or C
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