9. Which of the following pathways produces 2-hexanone? (i) 1-Hexyne is treated with Hg2+/dil. H2SO4. (ii) 3-Methylhept-2-ene is treated with O3 followed by hydrolysis. (iii) n-butyl magnesium bromide reacts with acetaldehyde followed by hydrolysis and then oxidation with chromic acid. (iv) Hydroboration-oxidation of 1-hexyne.

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How do you convert the following:

(i) Prop-1-ene to 1-fluoropropane

(ii) Chlorobenzene to 2-chlorotoluene

(iii) Ethanol to propanenitrile

What happens when

(i) n-butyl chloride is treated with alcoholic KOH?

(ii) 2, 4, 6-trinitrochlorobenzene is subjected to hydrolysis?

(iii) methyl chloride is treated with AgCN?

H_{2} O_{2}

C_{2} H_{5} - N = C = O

What happens when

(i) n-butyl chloride is treated with alcoholic KOH,

(ii) bromobenzene is treated with Mg in the presence of dry ether,

(iii) chlorobenzene is subjected to hydrolysis,

(iv) ethyl chloride is treated with aqueous KOH,

(v) methyl bromide is treated with sodium in the presence of dry ether,

(vi) methyl chloride is treated with KCN.

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