Which of the following pathways produces 2-hexanone?
(i)1-Hexyne is treated with `H_(2)SO_(4),HgSO_(4)` and water
(ii) 3-Methyl-2-heptene is treated with `O_(3)` followed by hydrolysis
n-Butyl magnesium bromide reacts with aetaldehyde followed by hydrolysis and then chromic acid oxidation
(iv) Hydroboration oxidation of 1-hexyne

Options

A. (i), (ii) and (iii)
B. (i) and (ii) only
C. (i), (ii) and (iv)
D. (i) and (iii) only

Answer

A

Explanation

(i) `underset("(1-hexyne)")(CH_3-CH_2)-CH_2-CH_2-C-=CH underset(H_2O)overset(HgSO_4//H_2SO_4)to underset("(2-hexanone)")(CH_3-CH_2)-CH_2-CH_2-underset(O)underset(||)C-CH_3`
(ii) `underset("(3- methyl-2-heptene)")(CH_3-CH=underset(CH_3)C-CH_2-CH_2-CH_2-CH_3) underset(H_2O)overset(O_3)to CH_3-underset(H)underset(|)C=O+O=underset(CH_3)underset(|)C-underset("(2-hexanone)")(CH_2-CH_2-CH_3)`
(iii) `CH_3-CH_2-CH_2-CH_2-MgBr+-CH_3-overset(O)overset(||)-H overset(H_2O)to CH_3-overset(OH)overset(|)underset(H)underset(|)C-CH_2-CH_2-CH_2-CH_3 overset(H_2CrO_4)to underset("(2-hexanone)")(CH_3-overset(O)overset(||)-CH_2-CH_2-CH_2-CH_3)`
(iv) `CH_3-(CH_2)_3-C-=CH underset(H_2O//OH^(-))overset(SiO_2//BH_3)to (CH_3)-(CH_2)_3-CH_2-CHO`