Question

Problem 10.57 ropose a plausible synthesis for the following transformations. Choose from reagents (A-H): B. 1) NaNH2 2) Mel 3) 9-BBN 4) H202, NaOH 1) Br2 2) Excess NaNH2 3) H20 1) Br2 2) Excess NaNH2 3) H20 4) H2S04. H20, HgSO 1) NaNHz 2) EtI 3) Na, NHa () 1) Excess NaNH2 2) H20 3) NaNH2 4) Mel 5) Na, NH3 C) 1) NaNH2 2) 3) H2, Pt 1) 9-BBN 2) H202, NaOH 1) Excess NaNH2 2) H20 3) Br2 (1 eq), cCl Reagents: A Divis on
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Answer #1

1) option B is correct

Explanation: Addition of Br2 to alkene produces a dibromo compound as product. dehydrohalogenation of dibromo compound with NaNH2 produces alkyne as product.

2) option C is correct

Explanation: Addition of Br2 to alkene produces a dibromo compound as product. dehydrohalogenation of dibromo compound with NaNH2 produces alkyne as product. Addition of H2O to alkyne produces ketone.

3) option D is correct

Explanation:NaNH2 is a strong base which abtracts acidic proton and produces acetylide ion which on further reaction with EtI produces an extended carbon chain. Reduction of triple bond with Na, NH3 produces trans-alkene as product.

4) option H is correct

Explanation:NaNH2 is a strong base which abtracts acidic proton and produces acetylide ion which on further reaction with CH3CH2CH2I produces an extended carbon chain. Reduction of triple bond with H2, Pt produces alkane as product.

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Problem 10.57 ropose a plausible synthesis for the following transformations. Choose from reagents (A-H): B. 1)...
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