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secondary alcohols
15

esters

12

21

Carboxylic 13
acids
11

di-bromo alkane

17

nitriles

amines

alcohol

20
10

16
Halo-alkanes
4

diols
alkanes

cyanohydrins
7

Primary alcohol

CO2 + H2O
9

alkenes
5

19
3

ketones

14

aldehydes

18
2,4-DNPH

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1 NH3 Ethanol/C2H5OH/alcohol solvent
2 KCN/NaCN Ethanol/C2H5OH/alcohol solvent
3 NaOH/KOH, Water/H2O as solvent, heat under reflux
4 Alcohol to Halo-alkanes (see next page)
5 Concentrated H2SO4/P4O10/Al2O3/Pumice (dehydration/elimination)
6 NaOH/KOH, Ethanol/C2H5OH/alcohol solvent, heat under reflux
7 HCN, KCN catalyst, alkaline condition or NaCN followed by H2SO4
8,14 K2Cr2O7/H+1, heat under reflux (strong oxidizing agent will convert it into CO2 and H2O), for (8) the
aldehyde produced is immediately distilled off
9 cold dilute alkaline KMnO4
10,11,12 - Concentrated KMnO4/H+1,heat under reflux (strong oxidizing agent required) (alkene double bond is
always broken, 10 CH2=, 11 R-CH=, 12 (R)2C=)
13 Tollens Reagent [Ag(NH3)2]+1 (silver mirror produced) or Fehling Solution + heat (red ppt formed)
14 see (8)
15 reflux with concentrated H2SO4 (esterfication/elimination/dehydration/condensation)
16 free radical subsititution
17 LiAlH4, or NaBH4 (reduction)
18 Yellow/Orange/Red ppt
19 steam with H3PO4 catalyst (60/70 atm pressure) or bubble through concentrated H2SO4 and then add
water and distil
20 Br2 in an inert solvent like CCl4 (electrophilic Addition)
21 Mineral acid (aq) except HNO3 + heat or NaOH, then aqueous mineral acid + heat

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2Na + 2C2H5OH (alcohols) 2C2H5ONa + H2 (slight effervescence seen)
4 Formation of Iodoalkanes from alcohols (red P + I2 or HI (aq) or KBr/Concentrated H3PO4 or PI3, heat
in all cases except with PI3)
4 Formation of chloroalkanes from alcohols (PCl5,room temperature/SOCl2 , all other products are
gases,
4 Formation of bromoalkanes from alcohols (NaBr + H2SO4,heat under reflux or Red Phosphorous +
Br2)