Devise a synthesis of 5-methyl-1-hexyne using one of the starting materials and any of the reagents...

Devise a synthesis of 5-methyl-1-hexyne 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:

(1.) HC(triple bonded)CH

(2.) HC(triple bonded)C-CH₃

(3.) HC(triple bonded)C-CH₂CH₃

(4.) HC(triple bonded)C-CH₂CH₂CH₂CH₃

(5.) HC(triple bonded)C-CH(CH₃)(CH₃)

(6.) HC(triple bonded)C-C(CH₃)(CH₃)(CH₃)

Reagents:

a. NaNH₂/NH₃ (l)

b. NaOH/H₂O

c. iodomethane

d. idoethane

e. 1-bromopropane

f. 2-bromopropane

g. 1-bromo-3-methylbutane

h. t-butyl bromide

i. H₂/ Pd on Carbon

Answer the following:

Starting Material:

Reagent for step 1:

Reagent for step 2:

Reagent for step 3:

** ALSO, PLEASE ANSWER THE SAME QUESTIONS USING: (Z)-4,4-dimethyl-2-pentene AND (E)-3-octene (Instead of 5-methyl-1-hexyne)

Solutions

Expert Solution

queen_honey_blossom answered 1 year ago

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