Question

Give the structure of the products you would expect from the reaction (if any) of 3-hexyne with:

One molar equivalent of HCl

Two molar equivalents of HCl

One molar equivalents of Br₂

Two molar equivalents of Br₂

H₂, Pd/C

Lindlar catalyst

Li/NH₃(l)

NaNH₂/NH₃(l)

1) 9-BBN 2) OH^-(aq), H₂O₂

H₂O, H⁺, Hg²⁺

1) O₃ 2)H₂O

Answer 1

Drawn below are the products formed when 3-hexyne reacts with the given reagents

addition of HCl is by Markovnikov's rule

Lindlar catalyst reduces alkyne to cis-alkene

Li,NH3(l) reduces alkyne to trans-alkene

H2.Pd/C fully reduces alkyne to alkane

Hydroboration of oxymercuration both yield the same product

Ozonolysis gives 2 moles of propanaldehyde