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mlee52381 mlee52381
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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/CH2Cl2 to yield an intermediate that reacts with LDA to yield intermediate X, which has a resonance form Y. 1-propanol also reacts with PCl3 to yield an intermediate Z that reacts with intermediate X, which undergoes the following series of reactions to yield the product: 1. Na2Cr2O7/H2SO4/H2O; 2. Excess CH3CH2CH2OH/H2SO4.

▸ 1-propanol reacts with PCC/CH2Cl2, then the product reacts with LDA to produce intermediate X, which has resonance forms. 1-propanol reacts with PCl3, then the product reacts with intermediate X to yield intermediate Y. Intermediate Y reacts with NaBH4/CH3OH to yield the product.

▸ 1-propanol reacts with PCl3 to yield intermediate X. 1-propanol also undergoes the following reaction sequence: 1. Na2Cr2O7/H2SO4/H2O; 2. excess CH3CH2CH2OH/H2SO4; 3. LDA; 4. Intermediate X. This yields the product.

▸ A or B

▸ B or C
Textbook 
Organic Chemistry

Organic Chemistry


Edition: 4th
Author:
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paris.chenparis.chen
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