Using any necessary inorganic reagents, show how you would convert acetylene and isobutylbromide to

(a)meso-2,7-dimethyloctane-4,5-diol,(CH₃)₂CHCH₂CH(OH)CH(OH)CH₂CH(CH₃)₂ .

(b) (± ) -2,7-dimethyloctane-4,5-diol

_{Reagents are compounds incorporated into a system to bring about a chemical reaction. Some examples of reagents include Collins reagent and Grignard reacgent.}

Alkene dihydroxilation constitutes a process that transforms an alkene to a vicinal diol. A transition metal possessing a high oxidation state like osmium or manganese are used in this oxidation reaction.

Diols are produced by the different reactions like the syn-dihydroxylation with O_SO₄or cold KMnO₄ . It can also be done via the anti-hydroxylation via an epoxide using peroxyacid and water. The problem utilized inorganic reagents, hence we requireO_SO₄ reagent than the peroxyacid that is organic.

(a)Part (a) needs the synthesis of meso isomer, hence, syn-addition happens on the cis-alkene.

The alkene must be cis to create a meso product from the syn addition. Hence, reduction is performed with Lindlar’s catalyst to generate the cis alkene.

(b)The alkene created must be trans to generate a(± ) product from the syn addition. Hence, reduction is done using Na/NH₃ .