To synthesize 3-octyne, you could use bromination and elimination from an intermediate created using which of the following sequences of reactions? 1) propyne, NaNH, 2) 1-bromopentane 3) aqueous H₂SO4, cat. HgSO4 OI II III O IV OV IV II 1) 1-butyne, NaNH, 2) 1-bromobutane 3) H₂, Lindlar's cat. 1) 1-butyne, NaNH, 2) 1-bromobutane 3) NaNHz,H2O III 1) propyne, NaNH, 2) 1-bromopentane 3) H₂, Ni₂B (P-2) 1) 1-butyne, NaNH, 2) 1-bromobutane 3) H₂, Pd/C

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions
Section19.SE: Something Extra
Problem 28VC
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To synthesize 3-octyne, you could use bromination and elimination from an intermediate created using which of the following
sequences of reactions?
1) propyne, NaNH,
2) 1-bromopentane
3) aqueous H₂SO4, cat. HgSO4
OI
II
III
O IV
OV
IV
II
1) 1-butyne, NaNH,
2) 1-bromobutane
3) H₂, Lindlar's cat.
1) 1-butyne, NaNH,
2) 1-bromobutane
3) NaNHz,H2O
III
1) propyne, NaNH,
2) 1-bromopentane
3) H₂, Ni₂B (P-2)
1) 1-butyne, NaNH,
2) 1-bromobutane
3) H₂, Pd/C
Transcribed Image Text:To synthesize 3-octyne, you could use bromination and elimination from an intermediate created using which of the following sequences of reactions? 1) propyne, NaNH, 2) 1-bromopentane 3) aqueous H₂SO4, cat. HgSO4 OI II III O IV OV IV II 1) 1-butyne, NaNH, 2) 1-bromobutane 3) H₂, Lindlar's cat. 1) 1-butyne, NaNH, 2) 1-bromobutane 3) NaNHz,H2O III 1) propyne, NaNH, 2) 1-bromopentane 3) H₂, Ni₂B (P-2) 1) 1-butyne, NaNH, 2) 1-bromobutane 3) H₂, Pd/C
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