Compound

Alkene (C=C)

Alkane
Halogenoalkane
(R-X)

Reactions undergone
Nucleophilic addition

With what compound?

H2, (Ni catalyst, 150C or Pt
catalyst)
Catalytic hydrogenation HX (RT), X is halogen
Electrophilic addition
Concentrated H2SO4, water

What is formed
Alkane

Oxidation with KMnO4

CHR end of alkene

CRR end of alkene
CH2 end of terminal alkene
X2, X is halogen

Aldehyde
Ketone
CO2, H2O
Halogenoalkane

NaOH, Reflux
NaCN, ethanolic, heat

Alcohol
Nitrile

Excess ammonia
Concentrated NaOH in ethanol,
reflux
Cr2O72- or KMnO4, acidified

Amine
Alkene

Free radical
substitution
Nucleophilic
substitution

Elimination
Alcohol (OH)

Oxidation

Nucleophilic
substitution
Dehydration
Iodoform test

PBr3, concentrated H2SO4,

refluxed
H2SO4, heat
Iodine and sodium hydroxide

Halogenoalkane
Alcohol

Aldehyde

Ketone
Halogenoalkane
Alkene
Carboxylate ion

Remarks

Position depends on stability and

where the C=C double bond was
(Markovnikovs rule)

Effervescence observed in QA
Markovnikovs rule applies (stability
and position)
OH group replaces halogen
CN group replaces halogen. One extra
Carbon.

Primary alcohol becomes this

*To get an aldehyde, use K2Cr2O7
acidified, heat w/ immediate distillation
Secondary alcohol becomes this

2 products, look at OH group

Pale yellow precipitate of CHI3 formed.

Aldehyde

Ketone

Oxidation

Tollens Reagent, warm

Fehlings Solution, warm
I2 (aq), NaOH, warm
K2Cr2O7 or KMnO4 oxidized

Carboxylate ion
Carboxylate ion
Carboxylate ion
Carboxylic acid

Nucleophilic addition

Condensation

HCN, KOH
HCN, KCN
KCN, H2SO4
2, 4-DNPH

Reduction
Oxidation

LiAlH4, dry ether

I2 (aq), NaOH, warm

Nitrile with
alcohol group
*Cyanohydrin
Orange
precipitate
Primary alcohol
Carboxylate ion

Nucleophilic addition

HCN, KOH
HCN, KCN
KCN, H2SO4
2, 4-DNPH

Condensation
Carboxylic acid

Fission of C-O bond

Nitrile

Reduction
Acidic hydrolysis

Alcohol, R-OH, with concentrated

H2SO4, heat
PCl5 or SOCl2
LiAlH4, dry ether
Dilute HCl

Reduction
Hydrolysis
Nucleophilic

LiAlH4, dry ether

Water
Alcohol

Acyl chloride

Nitrile with
alcohol group
*Cyanohydrin
Orange
precipitate
Ester
Acyl chloride
Alcohol
Carboxylic acid
Amine
Carboxylic acid
Ester

Silver mirror formed

Red PPT of Cu2O formed
Yellow PPT of CHI3 formed
From primary alcohol, can go straight
to this
One extra carbon than before

C=O bond cutaway

Yellow PPT of CHI3 formed.

This only happens with methyl ketones
One extra carbon than before (step up
reaction)
C=O bond cutaway
H2SO4 acts as a catalyst
White fumes observed as well
Ammonium chloride produced as a side
product
HCl byproduct

substitution
Benzene
*remark: ALL benzene
reactions apply for
methylbenzene as well.
*remark: the CH3 on
methylbenzene behaves
like a typical alkane.

Methylbenzene
Specific
Phenol

Electrophilic
substitution

Addition
Oxidation

Acylation
Electrophilic
substitution

Phenol
Amine, ammonia
Concentrated HNO3
Concentrated H2SO4
30C
Cl2, AlCl3

Ester
Amide

Alkaline medium PREFERRED

2,4 directing for methylbenzene

2,4 directing for methylbenzene

Br2, FeBr3

2,4 directing for methylbenzene

RCl, AlCl3
(Friedel-Crafts Alkylation)

2,4 directing for methylbenzene

Diagram is inaccurate

Acyl chloride, AlCl3

H2, Ni
Cr2O72- or KMnO4, acidified

Ester
Cyclohexane
Benzoic acid

Acyl chloride
Br2 in CCl4, room temperature
Br2 (aq)
Dilute HNO3, room temperature
Concentrated HNO3, room
temperature

Ester
Phenol with 1 Br
Phenol with 3 Br
Phenol with 1 NO2
Phenol with 3 NO2

2,4 directing for methylbenzene

EVERY SINGLE BENZENE RING WITH
ANY ALKYL GROUP ATTACHED DOES
THIS.
White fumes of HCl evolved
2,4 directing, applies to Cl2 as well
2 next to, 1 opposite
2,4 directing
2 next to, 1 opposite

Distinguishing tests to confirm whats what

- 2,4 DNPH: Used to confirm presence of aldehydes or ketones
- Sodium Carbonate: Only carboxylic acids react with it
- Iodoform test: Used to confirm presence of CH3CO group, as with a methyl-aldehyde, methyl ketone or methyl alcohol.
- Aqueous Bromine: Decolorizes when alkenes and phenols are present
- Bromine in CCl4: Decolorizes N-phenyl-ethanamides, (phenylamines,) phenols and alkenes.
- Tollens Reagent: Oxidizes aldehydes and benzaldehydes to form a silver mirror (Ag)
- Fehlings Reagent: Oxidizes aldehydes to form a reddish brown precipitate of copper (I) oxide.
o Cant oxidize benzaldehydes because alkaline condition causes benzaldehyde to disproportionate.
- Neutral iron (III) chloride: reacts with phenols to form a violet coloration