ADVANCED LEVEL CHEMISTRY PROBLEMS

ORGANIC SYNTHESIS/CONVERSIONS

1. Write equations to show how the following conversions can be made, and in each case,

state the conditions for the reactions.

(a). Propan-2-ol to propanal

(b). Cyclohexene to cylohaxanone

(c). 1-bromopropane to propanone

(d). 2-chloropropane to propanal

(e). Ethene to hexane-1,6-dioic acid

(f). Benzene to cyclohexene

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 (g). Benzene to methoxycyclohexane (cyclohexyl methyl ether)

(h). Ethanal to propanone

(i). Chloromethane to propanal

(j). Methanol to 1-bromopropan-2-ol

(k). 1-phenylethanol to 2-phenylethanol

(l). Methanol to 2-methylpropan-2-ol

(m). Methanol to 2-methylpropene

(n). Benzene to phenol

(o). Ethyne to methoxybenzene (methyl phenyl ether)

(p). Phenol to benzenesulphonic acid

(q). Benzene to 2,4,6-tribromophenol

(r). 1,2-dibromoethane to cyclohexylmethanol

(s). Benzene to phenyl ethanoate

(t). Cyclohexanol to cyclohexylmethanol

(u). Ethene to butanedioic acid

2. Write equations to show how the following compounds can be synthesised from benzene

and in each case, indicate the conditions for the reactions.

(a). 2-hydroxy-2-phenylpropanenitrile

(b). 1-bromo-1-phenylethane

(c). Phenylethene

(d). 1-phenylethane-1,2-diol

(e). 1-bromo-2-phenylethane

(f). Phenylethyne

(g). Poly(phenylethene)

𝑆𝑂3- 𝑁𝑎+
(h). 𝐶 − 𝐶𝐻3

𝑂𝐻

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 (i).
𝐶 = 𝑁𝑂𝐻

𝐶𝐻3

(j).
𝐶 = 𝑁𝑁𝐻𝐶𝑂𝑁𝐻2

𝐶𝐻3

3. Write equations to show how the following conversions can be made, and in each case,

state the conditions for the reactions.

(a). Ethene to 𝐶 = 𝑁𝑂𝐻

(b). But-2-ene to ethene

𝐻
(c). 2-bromopropane to 𝐶𝐻3 𝐶𝐻2 𝐶 = 𝑁𝑁𝐻𝐶𝑂𝑁𝐻2

(d). Propanone to 2-methylpropanenitrile

(e). Ethanal to methanal

𝐻
(f). Benzene to 𝑁𝑁

(g). 2-chloropropane to 2,2-dichloropropane

(h). 2,2-dibromopropane ` to (𝐶𝐻3 )2 𝐶 = 𝑁𝑁𝐻𝐶𝑂𝑁𝐻2

(i). Ethanol to butane-1,3-diol

(j). Ethene to 1,3-dichlorobutane

END

“Practice makes perfect”

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