Devise a synthesis of (E)-3-octene using one of the starting materials and any of the reagents below using the fewest steps possible. If you need fewer that the 3 steps allowed, enter "none" for reagents in the remaining unused steps. Starting materials HC=CH HCEC-CH, 1 Reagents a NaNH/NH (D b NaOH/H₂O ciodomethane Starting material Reagent for step 1 Reagent for step 2 Reagent for step 3 2 HC=C–CH,CH, 3 diodoethane e 1-bromopropane f 2-bromopropane HC=C–CH,CH,CH, CH, 4 g 1-bromo-3-methylbutane h t-butyl bromide i H₂/Pd on carbon CH₂ HC=C-C-CH₂ 5 j H₂/ Lindlar catalyst KHI NH(0) CH₂ HC=C-C-CH₂ CH₂ 6 I Na/NH₂(0)

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Devise a synthesis of (E)-3-octene using one of the starting materials and any of the reagents below using the fewest steps possible. If you need fewer that the 3 steps allowed, enter "none" for reagents in the remaining unused
steps.
Starting materials
HCECH HCEC-CH,
1
Reagents
a NaNH, NH()
b NaOH/H₂O
ciodomethane
Starting material
Reagent for step 1
Reagent for step 2
Reagent for step 3
2
HC=C–CH,CH,
3
diodoethane
e 1-bromopropane
f 2-bromopropane
HC=C–CH,CH,CH, CH,
4
g 1-bromo-3-methylbutane
ht-butyl bromide
i H₂/Pd on carbon
CH₂
HC=C-C-CH₂
H
5
k H'NH (I)
CH₂
HC=C-C-CH₂
CH₂
jH₂ Lindlar catalyst
I Na/NH₂(0)
6
Transcribed Image Text:Devise a synthesis of (E)-3-octene using one of the starting materials and any of the reagents below using the fewest steps possible. If you need fewer that the 3 steps allowed, enter "none" for reagents in the remaining unused steps. Starting materials HCECH HCEC-CH, 1 Reagents a NaNH, NH() b NaOH/H₂O ciodomethane Starting material Reagent for step 1 Reagent for step 2 Reagent for step 3 2 HC=C–CH,CH, 3 diodoethane e 1-bromopropane f 2-bromopropane HC=C–CH,CH,CH, CH, 4 g 1-bromo-3-methylbutane ht-butyl bromide i H₂/Pd on carbon CH₂ HC=C-C-CH₂ H 5 k H'NH (I) CH₂ HC=C-C-CH₂ CH₂ jH₂ Lindlar catalyst I Na/NH₂(0) 6
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