Y13 organics: deduce the reagents and conditions

Benzene to chlorobenzene

Cl2, AlCl3 catalyst, warm

Benzene to bromobenzene

Br2, FeBr3

Benzene to Nitrobenzene

Conc HNO3, conc H2SO4, warm

Benzene to alkylbenzene

Haloalkane, AlCl3 catalyst, reflux

Benzene to phenyl ketone

RCOCl, AlCl3 catalyst, reflux

Phenol to phenoxide salt and water

Alkaline conditions, often NaOH

Phenol to phenoxide salt and hydrogen

Metal, often Na

Phenol to azo dye

Add phenol to alkaline conditions, then add to diazonium salt

Phenol to 2,4,6-tribromophenol

Bromine water / Br2 (aq) [same as with phenylamine]

Phenol to nitrophenol

Dilute HNO3, 20 ºC

Phenylamine to 2,4,6-tribromophenylamine

Bromine water / Br2 (aq) [same as with phenol]

Phenylamine to diazonium salt

NaNO2 , HCl,

< 10ºC

Alkylbenzene to Benzoic Acid

KMnO4 and NaOH, followed by H+.

Alkylbenzene to chloroalkylbenzene (chlorine in the ring)

Cl2, AlCl3 catalyst, warm, sometimes in dark

Alkylbenzene to bromoalkylbenzene (bromine in the ring)

Br2, FeBr3 catalyst, warm, sometimes in dark

Alkylbenzene to chloroarene (chlorine on the sidechain)

Cl2, UV light / sunlight, boiling conditions

Alkylbenzene to 2-nitroarene or 4-nitroarene

Conc HNO3, conc H2SO4, warm [like with simple benzene]

Nitrobenzene to Phenylamine

Tin, conc. HCl, reflux then NaOH

Amine to amide

conc. acyl chloride in water, room temperature, no Lewis-Acid catalyst

Amide to amine (RCONHR' to RCH2NHR')

LiAlH4 in dry ether at room temperature [not reacting with a nitrile]

Amide hydrolysis to amine and carboxylate

aqueous acid or aqueous alkali, heat

Nitrile to Amine

H2, Ni catalyst

Acyl chloride to carboxylic acid

H2O, hydrolysis

Acyl chloride to ester

Alcohol, 20°C

Acyl chloride to phenyl ester

Phenol

Acyl chloride to simple amide (RCONH2)

conc solution of ammonia in water, room temperature

Acyl chloride to N-substituted amide

conc solution of amine in water