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

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Chemistry

Devise a synthesis of 5-methyl-1-hexyne usingone of the starting materials and any of the reagents below usingthe fewest steps possible. If you need fewer than the 3 stepsallowed, enter \"none\" for reagents in the remaining unusedsteps.

Starting Materials:

(1.) HC(triple bonded)CH

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

(3.) HC(triple bonded)C-CH2CH3

(4.) HC(triplebonded)C-CH2CH2CH2CH3

(5.) HC(triple bonded)C-CH(CH3)(CH3)

(6.) HC(triplebonded)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)

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