homologous series organic reactant reagents conditions organic product Name of Product other products type of reaction (bold

Name of Product other products type of reaction (bold - module 5) test result module
homolytic substitution (also
alkane CH3CH3 Cl2 or other halogen UV CH3CH2Cl halogenoalkane HCl referred to as free radical) N/A 1

CH3CH2Cl (N.B.
Markovnikov, H goes to
alkene CH2CH2 HCl or other H Halogen room temp C with most Hs) halogenoalkane electrophilic addition N/A 1

CH2BrCH2Br (technically
CH2OHCH2Br from
alkene CH2CH2 Br2 (or other halogen) room temp bromine water) dihalogenoalkane electrophilic addition orange to colourless 1
alkene CH2CH2 H2 Ni, heat CH3CH3 alkane reduction N/A 1
alkene CH2CH2 KMnO4 & NaOH room temp CH2OHCH2OH diol other stuff oxidation purple to colourless 1
alcohol CH3CH2OH Na metal room temp CH3CH2ONa alkoxide H2 acid/base bubbles, lit splint pops 1
haloalkane [order of
reactivity iodo then CH3CH2Cl HNO3, then AgNO3, white
bromo then chloro (could replace nucleophilic substitution [either ppte. (cream from bromide,
(due to bond strength)] Cl with Br or I) KOH in H2O heat under reflux CH3CH2OH alcohol KCl SN1 (tertiary) or SN2 (primary)] pale yellow from iodide) 2

haloalkane CH3CH2Cl KOH in alcohol heat under reflux CH2CH2 alkene KCl & H2O elimination N/A 2
nucleophilic substitution [either
haloalkane CH3CH2Cl excess NH3 in alcohol heat, sealed tube CH3CH2NH2 amine NH4Cl SN1 (tertiary) or SN2 (primary)] N/A 2
CH3CHO (aldehyde from other stuff
distil off (to avoid primary, ketone from (chromium (III) is
1o or 2o alcohol CH3CH2OH K2Cr2O7 & H2SO4 further oxidation) secondary) aldehyde or ketone the green colour) oxidation orange to green 2
other stuff
K2Cr2O7 & H2SO4 (or acidic (chromium (III) is
1oalcohol CH3CH2OH permangante) heat under reflux CH3COOH carboxylicacid the green colour) oxidation orange to green 2

alcohol CH3CH2OH PCl5 room temp CH3CH2Cl chloroalkane HCl & POCl3 nucleophilic substitution steamy white (acidic) fumes 2

alcohol CH3CH2OH NaBr & H2SO4 heat under reflux CH3CH2Br bromoalkane NaHSO4 & H2O nucleophilic substitution N/A 2
alcohol CH3CH2OH P & I2 warm CH3CH2I iodooalkane other stuff nucleophilic substitution N/A 2
"HCN" (hydrogen cyanide gas KCN + HCL pH5-
to dangerous to use, 8 (Or NaCN and CH3CHOHCN cyano hydrin /
carbonyl CH3CHO generated in situ) NaHSO4 at pH5) (cyanohydrin) hydroxynitrile nucleophilic addition N/A 4
CH3CH2OH (primary from
aldehyde, secondary primary or secondary
carbonyl CH3CHO Li AlH4 dry ether room temp from ketone) alcohol other stuff reduction N/A 4

C6H3(NO2)2NHN=CHCH3
conc.HCl room (2,4-DNPH + Melting point can be used 2,4-
carbonyl CH3CHO C6H3(NO2)2NHNH2 (2,4-DNPH) temp to identify) dinitrophenylhydrazone H2O condensation orange ppte. 4

yellow ppte., antiseptic smell

methyl carbonyl (Also (Tollens gives silver mirror,
works for secondary Fehling's goes green/brown
- (Iodoform)
methyl alcohol) CH3CHO NaOCl & KI or NaOH & I2 warm CHI3 & HCOO iodoform and carboxylate H2O oxidation are better tests) 4

aldehyde CH3CHO K2Cr2O7 & H2SO4 heat under reflux CH3COOH carboxylic acid other stuff oxidation orange to green 4

silver mirror (Tollens gives

silver mirror, Fehling's goes
aldehyde CH3CHO AgNO3 & NH3 heat under reflux CH3COO- carboxylate anion Ag oxidation green/brown are better tests) 4
 red precipitate (Tollens gives
silver mirror, Fehling's goes
aldehyde CH3CHO Benedicts or Fehlings heat under reflux CH3COO- carboxylate anion Cu2O oxidation green/brown are better tests) 4

carboxylic acid CH3COOH PCl5 room temp CH3COCl acid chloride HCl & POCl3 nucleophilic substitution steamy white (acidic) fumes 4
heat under reflux
carboxylic acid CH3COOH LiAlH4 in dry ether then HCl(aq) CH3CH2OH primary alcohol other stuff reduction N/A 4
carboxylic acid CH3COOH Na2CO3 or NaHCO3 room temp CH3COONa carboxylate anion H2O & CO2 acid/base bubbles, lime water milky 4

conc.H2SO4 heat CH3COOCH2CH3 (N.B.

carboxylic acid CH3COOH CH3CH2OH under reflux equilibrium; conc. acid shifts to ester) ester H2O esterification fruity smell 4

conc.H2SO4 heat
alcohol CH3CH2OH CH3COOH under reflux CH3COOCH2CH3 ester H2O esterification fruity smell 4

CH3CH2OH & CH3COOH

CH3COOCH2 (equilibrium; dil. acid
ester CH3 dil.H2SO4 heat under reflux shifts away from ester) carboxylic acid & alcohol H2O hydrolysis N/A 4

CH3COOCH2 CH3CH2OH & CH3COO-

ester CH3 NaOH heat under reflux (NOT equilibrium) alcohol & carboxylate ion H2O hydrolysis N/A 4
acid chloride CH3COCl H2O room temp CH3COOH carboxylic acid HCl hydrolysis N/A 4
acid chloride CH3COCl NH3 room temp CH3CONH2 amide HCl nucleophilic substitution N/A 4
acid chloride CH3COCl CH3CH2OH room temp CH3COOCH2CH3 ester HCl esterification N/A 4
nucleophilic substitution (From the
CH3CONHCH2CH3 (N- point of view of the acid chloride
acid chloride CH3COCl CH3CH2NH2 room temp substituted amide) n substituted amide HCl overall it is condensation) N/A 4

nitrile CH3CN H2SO4(aq) heat under reflux CH3COOH carboxylic acid NH4+ hydrolysis N/A 4
electrophilic substitution (From the
amine CH3CH2NH2 CH3COCl room temp CH3CONHCH2CH3 n substituted amide HCl point of view of the amine overall it N/A 5
amine CH3CH2NH2 CH3CH2Cl room temp (CH3CH2)2NH secondary amine HCl is condensation) N/A 5
2+
amine CH3CH2NH2 Cu room temp Cu(CH3CH2NH3)42+ tetraethylaminocopper(II) complex ion formation light to dark blue 5
amine CH3CH2NH2 H2O room temp CH3CH2NH3+ alkyl ammonium ion OH- acid/base UI blue 5
amine CH3CH2NH2 HCl room temp CH3CH2NH3+ alkyl ammonium ion Cl- acid/base N/A 5
arene C6H6 Conc HNO3&H2SO4 50-55oC C6H5NO2 nitrobenzene H2O electrophilic substitution N/A 5
AlCl3 & CH3COCl (Friedel
arene C6H6 Crafts) heat under reflux C6H5COCH3 phenylethanone HCl electrophilic substitution N/A 5
AlCl3 & CH3CH2Cl (Friedel
arene C6H6 Crafts) heat under reflux C6H5CH2CH3 phenylethane HCl electrophilic substitution N/A 5

arene C6H6 Conc H2SO4 heat under reflux C6H5SO3H benzenesulphonic acid H2O electrophilic substitution N/A 5
arene C6H6 Br2 & FeBr3 room temp C6H5Br bromobenzene HBr electrophilic substitution N/A 5
arene C6H6 H2 & Ni catalyst 150oC C6H12 cyclohexane reduction N/A 5

phenol C6H5OH Br2 room temp C6H2Br3OH tribromophenol HBr electrophilic substitution Br2 decoloured white ppte. 5
phenol C6H5OH HNO3 room temp C6H4(NO2)OH nitrophenol H2O electrophilic substitution N/A 5

nitro arene C6H5NO2 Sn & conc HCl heat under reflux C6H5NH2 phenylamine Sn(IV) reduction N/A 5
aryl amine C6H5NH2 HNO2 0-5 oC C6H5N2+ diazonium salt N/A 5
o
diazonium C6H5N2+ C6H5OH 0-5 C C6H5N2C6H4OH azo dye red/orange ppte. 5