AS Level · Chemistry 9701 · Introduction to Organic Chemistry
AS Organic Reactions
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Full text of AS Organic Reactions
Searchable version of Fahad Hameed's one-page AS Organic reaction map (2019, v2.0). The map is a hand-drawn diagram; this version lists every arrow on it as a reaction, with reagents and conditions, so it can be searched and copied. The original map is on the same page of megalecture.com.
Alkanes and halogenoalkanes
| From | Reagents and conditions | To |
|---|---|---|
| alkane, CH3CH2CH2CH3 | Br2, UV light | halogenoalkane, CH3CH2CH2CH2Br |
| alkene, CH3CH=CHCH3 | H2, Ni catalyst, heat | alkane, CH3CH2CH2CH3 |
| halogenoalkane, CH3CH2CH2CH2Br | NH3 in ethanol, or concentrated NH3, heat | amine, CH3CH2CH2CH2NH2 |
| halogenoalkane | NaOH in ethanol, heat under reflux (elimination) | alkene, CH3CH2CH=CH2 |
| halogenoalkane | KCN in ethanol, heat under reflux | nitrile, CH3CH2CH2CH2CN |
| halogenoalkane | NaOH(aq), heat under reflux (hydrolysis) | primary alcohol, CH3CH2CH2CH2OH |
| primary alcohol | HBr, or red P and Br2, heat | halogenoalkane, CH3CH2CH2CH2Br |
| secondary alcohol, CH3CH2CH(OH)CH3 | PCl5 (white fumes of HCl) | chloroalkane, CH3CH2CHClCH3 |
Nitriles and carboxylic acids
| From | Reagents and conditions | To |
|---|---|---|
| nitrile, CH3CH2CH2CH2CN | dilute HCl, heat under reflux (hydrolysis) | carboxylic acid, CH3CH2CH2CH2CO2H |
| carboxylic acid | PCl5 (white fumes of HCl) | acyl chloride, CH3CH2CH2CH2COCl |
| carboxylic acid, CH3CH2CO2H | NaOH(aq) (or a reactive metal) | salt of carboxylic acid, CH3CH2CO2− Na+ |
| ethanoic acid, CH3CO2H | Na | CH3CO2−Na+ + ½ H2 gas |
Alcohols, aldehydes and ketones
| From | Reagents and conditions | To |
|---|---|---|
| primary alcohol, CH3CH2CH2CH2OH | H+/K2Cr2O7, heat and distil off the aldehyde | aldehyde, CH3CH2CH2CHO |
| aldehyde | (1) H+/KMnO4, (2) H+/K2Cr2O7, (3) Fehling's, or (4) Tollens' reagent, heat | carboxylic acid, CH3CH2CH2CO2H |
| aldehyde | NaBH4(aq), or LiAlH4 in dry ether and heat, or H2/Ni and heat | primary alcohol |
| carboxylic acid | LiAlH4 in ether, heat | primary alcohol |
| secondary alcohol, CH3CH2CH(OH)CH3 | H+/K2Cr2O7 or H+/KMnO4, heat under reflux | ketone, CH3CH2COCH3 |
| ketone | H2/Ni at 200 °C, or NaBH4(aq), or LiAlH4 in dry ether, heat under reflux | secondary alcohol |
| ketone, CH3CH2COCH3 | HCN(aq) in KCN(aq), heat under reflux | hydroxynitrile, CH3CH2C(OH)(CN)CH3 |
| hydroxynitrile | dilute HCl or dilute H2SO4, heat under reflux | hydroxy acid, CH3CH2C(OH)(CO2H)CH3 |
| hydroxy acid | Na | the disodium salt, CH3CH2C(O−Na+)(CO2−Na+)CH3 |
| ketone, CH3CH2COCH3 | I2(aq) in NaOH(aq), warm (iodoform reaction) | salt of carboxylic acid, CH3CH2CO2− (+ CHI3) |
| secondary alcohol | Na | alkoxide, CH3CH2CH(O−Na+)CH3 + ½ H2 gas |
| secondary alcohol | CH3CO2H, concentrated H2SO4, heat (esterification) | ester, CH3CH2CH(CH3)OCOCH3 |
| ester | dilute HCl or NaOH(aq), heat (hydrolysis) | secondary alcohol + ethanoic acid |
Alkenes
| From | Reagents and conditions | To |
|---|---|---|
| alkene, CH3CH=CHCH3 | hot, acidified concentrated KMnO4 (oxidative cleavage) | ethanoic acid, CH3CO2H |
| alkene | cold, dilute KMnO4, alkaline (or acidic) | diol, CH3CH(OH)CH(OH)CH3 |
| alkene | Br2 in ethanol, or Br2(l) | dibromoalkane, CH3CHBrCHBrCH3 |
| alkene | steam and dilute H3PO4 at 350 °C and 70–100 atm | secondary alcohol, CH3CH2CH(OH)CH3 |
| dibromoalkane | NaOH(aq), heat under reflux | diol |
| dibromoalkane | NaOH in ethanol, heat under reflux | diene, CH2=CHCH=CH2 |
| diol | concentrated H2SO4 and heat, or hot alcohol vapour over Al2O3 | diene, CH2=CHCH=CH2 |
| secondary alcohol | concentrated H2SO4, heat (dehydration) | mixture of alkenes: CH3CH=CHCH3 and CH3CH2CH=CH2 |
| chloroalkane, CH3CH2CHClCH3 | NaOH in ethanol, heat under reflux | mixture of alkenes: CH3CH=CHCH3 and CH3CH2CH=CH2 |
| mixture of alkenes | H2, Ni, heat | alkane, CH3CH2CH2CH3 |
