[Review Topics] [References] Devise a synthesis of butane 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-CH, 1 Reagents 2 a NaNH,NH()) b NaOH/H₂O c iodomethane Starting material Reagent for step 1 Reagent for step 2 Reagent for step 3 Submit Answer HCEC-CH₂CH₂ 3 d iodoethane e 1-bromopropane f 2-bromopropane Retry Entire Group HCEC-CH₂CH₂CH₂CH₂ 4 g 1-bromo-3-methylbutane h t-butyl bromide i H₂/Pd on carbon. CH₂ CH₂ HC=C-C-CH₂ HC C-C-CH₂ H CH₂ 9 more group attempts remaining 5 6 jH₂! Lindlar catalyst KHINH ( I Na/NH₂ (D Previous Email Instructor Next Save and Exit

Organic Chemistry
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ISBN:9781305080485
Author:John E. McMurry
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Chapter22: Carbonyl Alpha-substitution Reactions
Section22.SE: Something Extra
Problem 64AP: The key step in a reported laboratory synthesis of sativene, a hydrocarbon isolated from the mold...
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[Review Topics]
[References]
Devise a synthesis of butane 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-CH,
1
Reagents
2
a Nanhbinh(D)
b NaOH/H₂O
c iodomethane
Starting material
Reagent for step 1
Reagent for step 2
Reagent for step 3
Submit Answer
HCEC-CH₂CH₂
3
diodoethane
e 1-bromopropane.
f 2-bromopropane
Retry Entire Group
HCEC-CH₂CH₂CH₂CH₂
4
g 1-bromo-3-methylbutane
h t-butyl bromide
i H₂/Pd on carbon
CH₂
HCEC-C-CH₂
H
5
9 more group attempts remaining
KHINH (1)
CH₂
HC=C-C-CH₂
CH₂
jH₂ Lindlar catalyst
I Na/NH₂ (D
6
Previous
Email Instructor
Next
Save and Exit
Transcribed Image Text:[Review Topics] [References] Devise a synthesis of butane 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-CH, 1 Reagents 2 a Nanhbinh(D) b NaOH/H₂O c iodomethane Starting material Reagent for step 1 Reagent for step 2 Reagent for step 3 Submit Answer HCEC-CH₂CH₂ 3 diodoethane e 1-bromopropane. f 2-bromopropane Retry Entire Group HCEC-CH₂CH₂CH₂CH₂ 4 g 1-bromo-3-methylbutane h t-butyl bromide i H₂/Pd on carbon CH₂ HCEC-C-CH₂ H 5 9 more group attempts remaining KHINH (1) CH₂ HC=C-C-CH₂ CH₂ jH₂ Lindlar catalyst I Na/NH₂ (D 6 Previous Email Instructor Next Save and Exit
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