Devise a synthesis of 1-pentyne using one of the starting materials and any of the reagents below using the fewest steps possible. If you need fewer than the 3 steps allowed, enter "none" for reagents in the remaining unused steps. Starting materials HCECH HOEC CHO 1 Reagents a NaNH, NH(I) b NaOH/H₂O c iodomethane 2 Starting material Reagent for step 1 Reagent for step 2 Reagent for step 3 HCEC-CH₂CH₂ 3 diodoethane e 1-bromopropane f 2-bromopropane CH₂ HC=C–CH,CH,CH, CHO HC C-C-CH₂ H 4 g 1-bromo-3-methylbutane h t-butyl bromide i H₂/Pd on carbon 5 CH₂ HC=C-C-CH₂ CH₂ к H I NЊ (!) I Na/NH₂(0) 6 jH₂ Lindlar catalyst

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Devise a synthesis of 1-pentyne using one of the starting materials and any of the reagents below using the fewest steps possible. If you need fewer than the 3 steps
allowed, enter "none" for reagents in the remaining unused steps.
Starting materials
HC=CH HC=C-CHO
1
Reagents
a NaNH, 1 NH (D)
b NaOH/H₂O
ciodomethane
2
Starting material
Reagent for step 1
Reagent for step 2
Reagent for step 3
HC=C–CH,CH,
3
diodoethane
e 1-bromopropane
f 2-bromopropane
HCEC-CH₂CH₂CH₂CH₂
4
g 1-bromo-3-methylbutane
h t-butyl bromide
i H₂/Pd on carbon
CH₂
HC=C-C-CH₂
5
H
k H'NH (I)
CH₂
HC=C-C-CH₂
CH₂
j H₂/ Lindlar catalyst
I Na/NH₂(0)
6
Transcribed Image Text:Devise a synthesis of 1-pentyne using one of the starting materials and any of the reagents below using the fewest steps possible. If you need fewer than the 3 steps allowed, enter "none" for reagents in the remaining unused steps. Starting materials HC=CH HC=C-CHO 1 Reagents a NaNH, 1 NH (D) b NaOH/H₂O ciodomethane 2 Starting material Reagent for step 1 Reagent for step 2 Reagent for step 3 HC=C–CH,CH, 3 diodoethane e 1-bromopropane f 2-bromopropane HCEC-CH₂CH₂CH₂CH₂ 4 g 1-bromo-3-methylbutane h t-butyl bromide i H₂/Pd on carbon CH₂ HC=C-C-CH₂ 5 H k H'NH (I) CH₂ HC=C-C-CH₂ CH₂ j H₂/ Lindlar catalyst I Na/NH₂(0) 6
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