Question 10 of 26advanced🔧 ApplyLong Answer5 marks

How the following conversions can be carried out?

(i)

Propene to propan-1-ol

Answer

Propene → 1-Bromopropane (HBr/peroxide) → Propan-1-ol (hydrolysis, context 6.17).

(ii)

Ethanol to but-1-yne

Answer

Ethanol → Ethyl bromide → Ethyne → But-1-yne (mentioned in context 6.11 i).

(iii)

1-Bromopropane to 2-bromopropane

Answer

1-Bromopropane → Propene (dehydrohalogenation, context 6.10) → 2-Bromopropane (HBr).

(iv)

Toluene to benzyl alcohol

Answer

Toluene → Benzyl chloride (Cl₂/light) → Benzyl alcohol (hydrolysis, context 6.17).

(v)

Benzene to 4-bromonitrobenzene

Answer

Benzene → Nitrobenzene (HNO₃/H₂SO₄) → 4-Bromonitrobenzene (Br₂/FeBr₃).

(vi)

Benzyl alcohol to 2-phenylethanoic acid

Answer

Benzyl alcohol → Benzyl chloride → Benzyl cyanide (KCN, context 6.15) → 2-Phenylethanoic acid.

(vii)

Ethanol to propanenitrile

Answer

Ethanol → Ethyl bromide → Propanenitrile (KCN, context 6.15).

(viii)

Aniline to chlorobenzene

Answer

Aniline → Benzene diazonium chloride (NaNO₂/HCl) → Chlorobenzene (CuCl).

(ix)

2-Chlorobutane to 3, 4-dimethylhexane

Answer

2-Chlorobutane → But-2-ene (dehydrohalogenation, context 6.10) → 3,4-Dimethylhexane (Wurtz).

(x)

2-Methyl-1-propene to 2-chloro-2-methylpropane

Answer

2-Methyl-1-propene + HCl → 2-Chloro-2-methylpropane.

(xi)

Ethyl chloride to propanoic acid

Answer

Ethyl chloride → Propanenitrile (KCN, context 6.15) → Propanoic acid.

(xii)

But-1-ene to n-butyl iodide

Answer

But-1-ene + HI/peroxide → n-Butyl iodide.

(xiii)

2-Chloropropane to 1-propanol

Answer

2-Chloropropane → Propene (dehydrohalogenation, context 6.10) → 1-Propanol.

(xiv)

Isopropyl alcohol to iodoform

Answer

Isopropyl alcohol → Acetone (oxidation) → Iodoform (I₂/NaOH).

(xv)

Chlorobenzene to p-nitrophenol

Answer

Chlorobenzene → p-Nitrochlorobenzene (HNO₃/H₂SO₄) → p-Nitrophenol (hydrolysis).

(xvi)

2-Bromopropane to 1-bromopropane

Answer

2-Bromopropane → Propene (dehydrohalogenation, context 6.10) → 1-Bromopropane (HBr/peroxide).

(xvii)

Chloroethane to butane

Answer

2 Chloroethane → Butane (Wurtz reaction).

(xviii)

Benzene to diphenyl

Answer

Benzene → Diphenyl (Wurtz-Fittig).

(xix)

tert-Butyl bromide to isobutyl bromide

Answer

tert-Butyl bromide → Isobutene (dehydrohalogenation, context 6.10) → Isobutyl bromide.

(xx)

Aniline to phenylisocyanide

Answer

Aniline → Benzene diazonium chloride (NaNO₂/HCl) → Phenylisocyanide (KCN, context 6.15).

Explanation

These conversions use concepts shown in the context: hydrolysis (6.17), dehydrohalogenation (6.10), KCN reactions (6.15), and S_N2 mechanisms (6.15, 6.16, 6.9). Conversions (ii) and (iv) are mentioned in context 6.11. The context demonstrates that benzyl halides undergo hydrolysis (6.17), alkyl halides undergo dehydrohalogenation (6.10), and KCN reacts with alkyl halides via S_N2 mechanism (6.15).