Whats added: Halogen (X2) In the presence of UV light In organic solvent (e.g.

: CCl4), room temperature in the absence of UV light In organic solvent (e.g.: CCl4), room temperature In water (aq), room temperature in the absence of light In water (aq), room temperature X2 in AlX3 or Fe or FeX3 as catalyst, room temperature X2 in AlX3 or Fe or FeX3 as catalyst, room temperature, dark Aqueous iodine in NaOH pale yellow ppt of CHI3

FRS EA ES EA ES ES ES

[Possible presence of] Alkanes, alkyl groups on benzene, etc Alkenes Phenol Alkenes Phenol Benzene Benzene with alkyl group(s) of

Oxidation Specific structure alcohol/carbonyl compound

Dry HX (g) Room temperature EA Alkenes HBr / HI / (HCl + ZnCl2) Substitution Alcohols

H2O H2O (g), i.e.: steam Heat in the presence of H3PO4 catalyst at 300 OC, 70 atm EA Alkenes

H2SO4 [different roles as a reagent, catalyst and dehydrating agent] Cold concentrated H2SO4, followed by H2O EA and heat Excess concentrated sulfuric acid, heat at 170 Elimination O C Concentrated HNO3 and concentrated H2SO4 ES (catalyst), reflux at 50 - 60 Concentrated HNO3 and concentrated H2SO4 ES (catalyst), reflux at 30 Alcohol, concentrated H2SO4 catalyst, reflux Substitution/ condensation NA KCN + H2SO4, 10-20

Alkenes Alcohols Benzenes Benzenes with activating groups Carboxylic acid Carbonyl compounds

H2 (g) Heat in the presence of Ni catalyst at 150 OC Pass over Pt catalyst at room temperature H2 (g), Ni catalyst, heat Heat in the presence of Ni catalyst, high pressure Heat in the presence of Ni catalyst, high pressure, 180 OC

Reduction Alkenes Reduction Nitriles Reduction Aldehydes / Ketones Reduction Benzene

LiAlH4 in dry ether LiAlH4 in dry ether LiAlH4 in dry ether, hydrolysis

followed

Reduction Nitriles by Reduction Aldehydes, acids

ketones,

carboxylic

NaBH4 In methanolic solution Reduction Aldehydes / Ketones

KMnO4 Cold dilute alkaline KMnO4

Mild oxidation Hot, concentrated acidified KMnO4 (possible effervescence) Strong oxidation Hot, concentrated acidified KMnO4 formation of white Strong ppt (possible effervescence) oxidation KMnO4 Strong oxidation

Alkenes Alkenes Benzene 1o or alcohols 2o

K2Cr2O7 K2Cr2O7 Strong oxidation 1o alcohols K2Cr2O7 with distillation Mild oxidation 1o alcohols

H3PO4 Phosphoric acid, heat at 200 OC Elimination Alcohols

Al2O3 Heat at 360 OC with Al2O3 Elimination Alcohols 500oC, Al2O3 and ? promoters Cracking Alkanes

Alcoholic KOH, reflux

Elimination

Halogenoalkanes

Aqueous NaOH / KOH, reflux Aqueous NaOH, reflux Aqueous NaOH or KOH, room temperature Acyl chloride, room temperature, NaOH (aq)

NS Halogenoalkanes Base hydrolysis Nitriles Neutralization Phenol Substitution / Phenol Acylation HCN + trace amount of NaOH (aq) catalyst, 10-20 NA Carbonyl compounds Alkaline solution of complex copper (II) ion, a deep Oxidation Aliphatic blue solution (Fehlings) Red/reddish-brown aldehydes precipitate of copper (I) oxide will be observed Aqueous NaOH or KOH, reflux Base hydrolysis Esters

HCl or H2SO4 (aq), reflux

Acid hydrolysis Dilute HNO3, room temperature ES Concentrated HNO3 and concentrated H2SO4 at room temperature ES yellow ppt Dilute HCl/H2SO4 (aqueous mineral acids), reflux Acid hydrolysis

Nitriles Phenol Phenol Esters

Acyl chloride Acyl chloride, room temperature Substitution/acylation Alcohols Acyl chloride, room temperature, NaOH (aq) Substitution / Acylation Phenol

KCN or NaCN in ethanol, reflux HCN + trace amount of NaOH (aq) catalyst, 10-20 HCN + trace amount of NaCN as catalyst, 10-20 KCN + H2SO4, 10-20

NS Halogenoalkanes NA Carbonyl compounds

NH3 NH3 (excess) in ethanol, heat in a NS sealed tube (prevent loss of ammonia) Aqueous solutions of ammonia and Oxidation silver nitrate silver mirror NH3, room temperature Nucleophilic acyl substation (condensation) Amines, room temperature Nucleophilic acyl

Halogenoalkanes

Methanoic acid / aliphatic and aromatic aldehydes Acyl chlorides Acyl chlorides

substation (condensation)

PX3 or red P with X2 PX3 or red P with X2 Substitution Alcohols, Carboxylic acids

Neutral FeCl3 Add aqueous FeCl3 violet complex

Phenol

H2O Water, room temperature Nucleophilic acyl substitution Acyl chloride

PCl5 PCl5 Substitution -OH group in alcohols or carboxylic acids

SOCl2 in pyridine SOCl2 in pyridine Substitution Alcohols / carboxylic acids

Na Na, room temperature Redox Alcohols / Phenols / Carboxylic acids

2,4-dinitrophenylhydrazine 2,4-dinitrophenylhydrazine with warming orange ppt Oxidation Ketones

Tollens reagent Aqueous solutions of ammonia and silver Oxidation Methanoic acid / aliphatic and nitrate silver mirror aromatic aldehydes

Fehlings reagent alkaline solution of complex copper (II) ion, a deep blue solution Oxidation Aliphatic Red/reddish-brown precipitate of copper (I) oxide will be aldehydes observed