The synthesis of the two isomers nonanal and 2-nonanone using alkenes with fewer

Question

The synthesis of the two isomers nonanal and 2-nonanone using alkenes with fewer than six carbon atoms involves several steps. Identify the reagents involved in the conversion of 1-heptene to nonanal as per the scheme given below.

The synthesis of the two isomers nonanal and 2-nonanone using alkenes with fewer than six carbon atoms involves several steps. Identify the reagents involved in the conversion of 1-heptene to nonanal as per the scheme given below.

HBr/ROOR; Sodium acetylide; 9-BBN/HO2+NaOH. Sodium acetylide; HBr/ROOR; H2SO4+H2O/HgSO4. Sodium acetylide; 9-BBN/H2O2+NaOH; HBr/ROOR. HBr/ROOR; Sodium acetylide; H2SO4+H2O/HgSO4.

Explanation / Answer

Conversion of 1-heptene to nonanal

Synthesis begins with hydrobromination in presence of peroxide to give 1-heptyl bromide. Couping with sodium acetylide give 1-nonyne which is then hydroborated and oxidative reaction gives the terminal aldehyde product.

Reagents would be thus,

HBr/ROOR, Sodium acetylide, 9-BBN/HO2+NaOH

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