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Question

Assume general laboratory reagents are available.
Which of the following sequences could synthesize the following compound from the indicated starting material:


A

1: Dissolved metal reduction 2: Carboxylation 3: LindlarH2

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B

1: Na/ethanol 2: Carboxylation 3: LindlarH2

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C

1: NaBH4 in ethanol 2: Carboxylation 3: LindlarH2

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D

1: NaNH2 in NH3 2: CO2 followed by H3O+ 3: LindlarH2

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