Chemical Reactions

Prefix
Priority Functional group Formula Suffix
(radical name)
1st Carboxylic acid -COOH carboxy- –oic acid
2nd Ester -COOR Alkoxycarbonyl- alkyl -oate
3rd Amide -CONH2 amido- -amide
4th Aldehyde -CHO formyl- -oxo, -al
5th Ketone -CO oxo- -one
6th Alcohol -OH hydroxy- -ol
7th Amine -NH2 amino- -amine
8th Ether -O- Alkoxy-, oxa- -ether
9th Alkene C=C alkenyl- -ene
10th Alkyne CC alkynyl- -yne
11th Halogen -X halo-
12th Alkane -R alkyl- -ane
13th Nitro -NO2 Nitro-
 hydrocarbons
Alkanes, alkenes, alkynes, and aromatic compounds
Combustion or Oxidation

CH4 + 2 O2 ∆ CO2 + 2 H2O + Heat

methane (alkane)

CH3 -
CH = CH2 + 9/2 O2 3CO2∆ + 3H2O + Heat
propene (alkene)

CH ≡ CH + 5/2 O2 ∆ 2CO2 + H2O + Heat

ethyne (alkyne)

+ 15/2 O2 ∆ 6CO2 + 3H2O + Heat

benzene (aromatic compounds)

Halogenation in Alkanes (Substitution reaction)
UVlight/∆/H2O2
CH3 – CH3 + Cl2 CH3 – CH2- Cl + HCl
ethane HCl Chloroethane chlorhydric acid

X2 = F2, Cl2, Br2 and I2

Halogenation in alkenes (Addition reaction)

CH3 – CH = CH2 + Cl2 CH 3 – CH – CH2

Propene (Br2, I2) │ │

Cl Cl 1,2-dichloro propane
Halogenation in alkynes (Addition reaction)
Cl Cl
+ Cl2 │ │
CH ≡ CH + Cl2 CH = CH CH — CH

Ethyne │ │ │ │

Cl Cl Cl Cl

1,2-dichloroethene 1,1,2,2-tetrachloroethane
Halogenation in Aromatic Compounds
Their characteristic reactivity is reactions of electrophilic substitution (ionic)

CH

CH CH

Br
FeBr3
CH CH
+ Br2HBr + HBr
CH

benzene Bromobenzene

∆ (700-900°C
ALKANES DEHYDROGENATION (At high temperatures 700ºC-900ºC)
H2
ALKANE ALKENE + H2
∆ (700-900°C

CH3—CH2—CH2—CH2—CH3 CH3—CH=CH—CH2—CH3 + H2
Pentane 2-pentene
Catalytic addition of Hydrogen in alkenes (Reduction of alkenes)

CH3 – CH = CH2 + H2 Pd/Pt/Ni CH3 – CH2 – CH3

(propene) (propane)

Catalytic addition of Hydrogen in alkynes (Reduction of alkynes)

+ H2
CH3 – C ≡ CH + H2 Pd/Pt/Ni CH3 – CH = CH2 Pd/Pt/Ni CH3 – CH2 – CH3
(propyne) (propene) (propane)

CH3 – C ≡ CH + 2H2 Pd/Pt/Ni CH3 – CH2 – CH3

(propyne) (propane)
Addition of Hydrogen Halide (HX) in alkenes
Hydrogen halides added across the double bond of the alkenes form alkyl halides.

CH3 – CH = CH2 + HI CH3 – CH – CH2 = CH3 – CH – CH3

Propene Hydrogen Iodide │ │ 2-Iodopropane │

(HBr, HCl) I H I

The Markownikoff’s Rule . In the ionic addition of an acid to the carbon-carbon double
bond of an alkene or triple bond of an alkyne, the hydrogen of the acid attaches itself to
the carbon atom that already holds the greater number of hydrogens.
Addition of Sulphuric acid and Water to alkenes and alkynes
When alkenes are added concentrated sulphuric acid, they yield alkyl hydrogen sulphates.Adding water and heat
afterwards, they produce alcohol and sulphuric acid (according to Markownikoff’s rule)

(Iso-propyl hydrogen sulphate)

CH3 – CH = CH2 + H2SO4 CH3 – CH – CH3
(propene) [ -OSO3H + H+] │
OSO3H

CH3 – CH – CH3 + H2O + heat CH 3 – CH – CH3 + H2SO4

│ [-OH + H+] │
OSO3H = H2SO4 OH propanol

Oxidation of alkenes with potassium permanganate. Alkenes react with an aqueous KMnO4 solution
in the cold producing glycol.
H+

CH3 – CH = CH – CH3 + KMnO4 CH3 – CH – CH – CH3

│ │
OH OH (Glycol) (alcohols family = two _OH groups)
Nitration of aromatic compounds
NO2

H2SO4
+ HNO3 60°C

benzene nitric acid nitrobenzene

Alkylation of aromatic compounds (Friedel-Crafts reaction)

HCl
CH CH – CH3
CH CH │
AlCl3 CH3 + HCl
+ CH3 ─ CH ─ Cl
│
CH CH

CH CH3

benzene chloroisopropane Isopropyl benzene

alcohols
 Alcohols oxidation
Primary alcohols can be oxidized into aldehydes and later into carboxylic acids
through partial oxidations with potassium dichromate (K2Cr2O7)

R - CH2 - OH + K2Cr2O7 H+
R - CH = O + H2 aldehyde

R - CH = O + K2Cr2O7 H+
R – COOH carboxylic acid

Total Oxidation with potassium permanganate (KMnO4)

R - CH2 - OH + KMnO4
H+
R – COOH carboxylic acid

Secondary alcohols can be oxidized into ketones.

H+
R—CH—R + K2Cr2O7 R— C —R + H2 ketone

OH O CH3

CH3— C —CH3
Tertiary alcohols do not react (The tertiary carbon with the attached hydroxyl group
OH
doesn’t have any free hydrogen)
Esterification
Alcohols yield esters when reacting with carboxylic acids.

(alcohol) (carboxylic acid) (ester)

CH3- OH + CH3 – COOH H2SO4
CH3 –CO-O- CH3 + H2O
methanol (ethanoic acid) methyl ethanoate
H 2O

Alcohols form Alkyl halides

R – CH2 – OH + HX R – CH2 – X + H2O

HX= HBr, HI, HCl H 2O Alkyl halide

CH3-CH2-CH2-OH + HCl CH3-CH2-CH2- Cl + H2O

propanol chlorhydric acid 1-chloro propane
ALCOHOLS DEHYDROGENATION (using H2SO4 as a catalyst)
H2SO4
ALCOHOL ALKENE + H2O

OH H2O

H2SO4
CH3—C—CH2—CH2—CH3 CH3—C = CH—CH2—CH3 + H2O

2-cyclopropyl-2-pentanol 2-cyclopropyl-2-pentene

(this is an obtaining reaction of 2-cyclopropyl-2-pentene)

Aldehydes and ketones
Aldehydes and ketones
Aldehydes can be hydrogenated forming alcohols.

Pt
CH3 ─ CHO + H2 CH3 ─CH2 ─ OH

Aldehydes react intensely with Halogens.

O
CH3 ─ CHO + Cl2 CH3 ─ C + HCl
HCl Cl

Aldehydes can be easily oxidized forming carboxylic acids.

H+
• CH3 – CH = O + KMnO4 CH3 – COOH
Carboxylic acids
Salt Formation
Because of their enhanced acidity, carboxylic acids react with bases to
form ionic salts

R – COOH + NaOH R – COO-Na + + H2O

(acetic acid) (sodium hydroxyde)

CH3COOH + NaHCO3 CH3COONa + CO2 + H2 O

(ethanoic acid) (sodium bicarbonate) (sodium ethanoate)
(baking soda)

Ester formation
It is the reaction of a carboxylic acid with an alcohol toOyield a new class of
compound called an ester. H SO 2 4

CH3­COOH + CH3­CH2­OH CH3-C-O-CH2-CH3 + H2 O

H2O
Reduction
Acyl Chlorides are reduced to aldehydes by
reduction with LiAlH (powerful metal hydride
reagent), or by H2 and a poisoned catalyst.

ether

(lithium aluminum hydride)

4 RCOOH + 3 LiAlH4
H2O

4 H2 + 4 RCH2OM + metal oxides

4 RCH2OH + metal hydroxides

Obtaining Reactions of carboxylic acids

From the Grignard reagent carboxylation

CH3CH2OCH2CH3 H+
R – MgX + CO2 R – C – OMgX R – C – OH
diethyl ether
(grignard reagent)
|| ||
O O

Mg(OH)X
Esters
Esterification
Reaction between an alcohol and a carboxylic acid along with an acid
catalyst which produces esters.

H2O

O O
H2SO4

R – C - OH + R´- OH R – C – O – R´ + H2O
Hydrolysis
Esters react with water and acid catalyst yielding into carboxylic
acid and alcohol
O O
H2SO4
H — C —O—CH2CH3 + H2O H — C—OH + HO—CH2CH3
[-OH + H+]
Hydrolysis

If an ester at high temperature and pressure reacts using CuO as

catalyst, alcohols are produced.

2H2
CH3-CO-O-CH3 CH3-CH2-OH + HO-CH3
CuO + 250°C + 220 Atm

Saponification
Esters react with bases producing the salt of the carboxylic acid
and alcohol
O O
 
CH3C—OCH2CH3 + NaOH CH3C—O– Na+ + HO-CH2CH3

salt of carboxylic acid

Amides
Amides
Considered as the least reactive acid derivative due to the
transference of the lone pair electrons of the amino group.

The characteristic chemical reaction of amides is the hydrolysis

(chemical reaction with water), through which the amides are
converted into acids and amines. This reaction is generally slow
unless catalyzed by a strong acid, an alkali, or an enzyme.
O
O

R-C-N-H
[-OH + H+]
H2O
R-C-OH + H-N-H
R’ R’

Amide Carboxylic acid Amine

Amides reduction

Primary amide

Secondary amide

Tertiary amide
Obtaining reactions
Amides can be obtained from carboxylic acids and
ammonia.
H2O

NaOH
R-COOH + NH2-H R-CO-NH2 + OH-H
(NH3) (H2O)

NaOH

CH3-COOH + NH3 CH3-CO-NH2 + OH-H

Ethanamide water
Amines
Amines
Salts formation (ammonium salts and diazonium salts)
Tertiary amines (R3N) react with strong acids (HI, HBr and HCl) in
neutralization reactions forming ammonium salts (R3NH+).
CH3-NH2 + HCl CH3-NH3+ Cl–
Methylamine methylammonium chloride
Ammonium salts are solid at room temperature, soluble in water and body fluids, and they
are used in drug processing. Cocaine is an ammonium salt which can react with NaOH
producing a type of free amine known as “crack”.

Chemical reactions of amines with nitric acid (HNO3) yield a very reactive
diazonium cation. This reaction is of great interest with aromatic amines
which introduces a wide variety of groups on benzene.
 Amines react with H2O yielding –OH ions.
NH3 + H2O  NH4+ + OH-
RNH2 + H2O  RNH3+ + OH-

Primary and secondary amines react with acid halides to form amides.

The amine nitrogen reacts with the carbonyl group and displaces the chlorine atom.
Hofmann transposition (rearrangement) of amides
In the presence of a strong base, primary amides react with
chlorine or bromine to give rise to amines with the loss of the
carbonyl carbon atom.This reaction is used to synthesize primary
alkyl and aryl amines.

Hofmann transposition

Primary
amide
amine
The product will have one carbon atom less per carbonyl group than the starting material.