Download ALKANE OR PARAFFIN SERIES

ORGANIC CHEMISTRY
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ALKANE OR PARAFFIN SERIES
Alkanes names end in "-ane." Saturation makes the alkanes relatively stable.
TYPE REACTIONS (with alkanes)
1. Oxidation (Combustion or Burning):
a) Complete: CnH2n+2 + O2 ----> CO2 + H2O
b) Incomplete:
CnH2n+2 + O2 ---->
C + H2O
or C + CO2 + H2O
2. Substitution:
C2H6 + Br2 ----> C2H4Br2 + H2
ALKENES (ETHYLENE SERIES)
Double bonded hydrocarbons; the names of alkenes end with "-ene."
TYPE REACTIONS
1. Oxidations:
• similar to alkanes
• same products
2. Substitutions:
• slow and difficult
• require catalysts
C2H4 + Br2 ----> C2H2Br2 + H2
1,1 - dibromoethene
trans - 1,2 - dibromoethene
ISOMERS
(opposite sides)
cis - 1,2 - dibromoethene
(same side)
3. Additions:
There are four types, all easy, because all involve the breaking of the
double bond which is not difficult.
a) Hydrogenation:
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b) Halogenation:
c) Hydrolysis:
d) Self-Addition (Polymerization):
1st stage
2nd stage
many stages
PREPARATION
Alkenes are made by removing hydrogen from alkanes; this process is called
Dehydrogenation.
ie.
ALKYNES (ACETYLENE SERIES)
Triple bonded hydrocarbons; the names end in "-yne."
TYPE REACTIONS
1. Oxidations:
2. Substitutions:
similar to alkenes.
3. Additions:
PREPARATION
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DEHYDROGENATION of the alkene;
ie.
The names all end in "- anol." There are three main types namely: MONOHYDROXYL
{CnH2n+1OH}, DIHYDROXYL {CnH2n(OH)2}, and TRIHYDROXYL {CnH2n-1(OH)3}
Functional Group:
R - OH where R is the rest of the compound.
TYPE REACTIONS
1. Oxidations
primary alcohols (1°) + O2 ----> aldehydes
secondary alcohols (2°) + O2 ----> ketones
PREPARATION
By hydrolysis of alkenes;
ie.
ie.
alkene + water ----> alcohol
C
C
+ H2O
---->
- C - C - OH
ALDEHYDES
The IUPAC names end in "-anal."
General Formula:
CnH2nO
Functional Group:
R-C
is called the carbonyl group (CHO); it is always at the end of the chain therefore there is
no number in the names.
TYPE REACTIONS
1. Oxidations
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aldehyde + O2 ----> carboxylic acid
PREPARATIONS
by oxidation of a primary alcohol
ie.
- C - C - OH
-C-C
ethanol
ethanal
CARBOXYLIC ACIDS
The IUPAC names end in "-anoic acid."
General Formula:
CnH2nO2
Functional Group:
R-C
is called the carboxyl group (COOH); it is always at the end of the chain therefore there is
no number in the names.
TYPE REACTIONS
1. Oxidations:
carboxylic acid + O2 ----> H2O + C &/or CO2
(complete or incomplete combustion)
PREPARATION
by oxidation of an aldehyde
ie.
-C
+
/2 O2
1
---->
-C
methanal
methanoic acid
KETONES
The IUPAC names end in "-anone."
SCH OAC ORGANIC CHEMISTRY
General Formula:
Functional Group:
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CnH2nO !!!
R-C
in which R and R1 represent roots which may or may not be the same.
TYPE REACTIONS
1. Oxidations:
ketones + O2 ----> H2O + C &/or CO2
(complete or incomplete combustion)
PREPARATION
by oxidation of secondary alcohols (2°) by dehydration
ie.
-C-C-C-
+
/2 O2
1
----> - C - C - C -
2-propanal
+ H2O
propanone
ETHERS
The IUPAC names end with a separate word, "ether."
General Formula:
Functional Group:
CnH2n+2O
R - O - R1
in which R and R1 represent roots which may or may not be the same.
PREPARATION
by condensation (dehydration) of alcohols
ie.
- C - C - OH + HO - C - C -
---------->
- C - C - O - C - C - + H2O
ethanol
ether
or
2 C2H5OH
---------->
C4H10O + H2O
AMINES
The IUPAC names end in "-amine."
SCH OAC ORGANIC CHEMISTRY
General Formula:
Functional Group:
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CnH2n+3N
or
CnH2n+1N2
R-N
PREPARATION
by substitution;
alkyl halide + ammonia
ie.
- C - C - Br +
N
---->
amine + H-halide
---->
-C-C-N
+ HBr
ESTERIFICATION: A TYPE REACTION
Esterification is the reaction between an organic acid and an alcohol to produce an ester,
which is an organic salt, and water.
CH3COOH + C2H5OH
ethanoic acid
(acetic acid)
+
ethanol
=
CH3COOC2H5 + H2O
=
ethyl ethanoate
(ethyl acetate)
+
water
ESTERS
The IUPAC names end in "-amine."
General Formula:
CnH2nO2
Functional Group:
R-C
where R is the hydrocarbon part of the acid and R1 is the hydrocarbon part of the alcohol.
AMIDES
The IUPAC names end in "-amide."
General Formula:
Functional Group:
CnH2n+1NO
R-C
PREPARATION
1. carboxylic acid + ammonia
ie.
R - COOH + NH3 ---->
R - CONH2 + H2O
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ie.
-C
+ N
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---->
methanoic acid
(formic acid)
-C
+ H2O
methanoamide
(formamide)
2. ester + ammonia
ie.
-C-C
+
N
---->
methyl ethanoate
(methyl acetate)
-C-C
ethanoamide
(acetamide)
+
- C - OH
methanol
3. ester + amine
ie.
-C-C
methyl ethanoate
(methyl acetate)
+
-C-C-N
ethylamine
---->
-C-C
ethylethanoamide
+
- C - OH
methanol
CYCLIC ORGANICS
Cyclic organics form a ring in which all the carbon atoms are bonded together.
example;
AROMATIC ORGANICS
ie. benzene; C6H6
For
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ALKANE TYPE REACTIONS
1. Oxidation (Combustion or Burning):
a) Complete: CnH2n+2 + O2 ----> CO2 + H2O
b) Incomplete:
CnH2n+2 + O2 ---->
C + H2O
or C + CO2 + H2O
2. Substitution:
C2H6 + Br2 ----> C2H4Br2 + H2
ALKENE TYPE REACTIONS
1. Oxidations:
• similar to alkanes
• same products
2. Substitutions:
• slow and difficult
• require catalysts
C2H4 + Br2 ----> C2H2Br2 + H2
1,1 - dibromoethene
trans - 1,2 - dibromoethene
ISOMERS
(opposite sides)
cis - 1,2 - dibromoethene
(same side)
3. Additions:
There are four types, all easy, because all involve the breaking of the
double bond which is not difficult.
a) Hydrogenation:
b) Halogenation:
c) Hydrolysis:
d) Self-Addition (Polymerization):
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1st stage
2nd stage
many stages
PREPARATION
Alkenes are made by removing hydrogen from alkanes; this process is called
Dehydrogenation.
ie.
ALKYNE TYPE REACTIONS
1. Oxidations:
2. Substitutions:
similar to alkenes.
3. Additions:
PREPARATION
DEHYDROGENATION of the alkene;
ie.
ALCOHOL TYPE REACTIONS
1. Oxidations
primary alcohols (1°) + O2 ----> aldehydes
secondary alcohols (2°) + O2 ----> ketones
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PREPARATION
By hydrolysis of alkenes;
ie.
alkene + water ----> alcohol
ie.
C
C
+ H2O
---->
- C - C - OH
ALDEHYDE TYPE REACTIONS
1. Oxidations
aldehyde + O2 ----> carboxylic acid
PREPARATIONS
by oxidation of a primary alcohol
ie.
- C - C - OH
-C-C
ethanol
ethanal
CARBOXYLIC ACID TYPE REACTIONS
1. Oxidations:
carboxylic acid + O2 ----> H2O + C &/or CO2
(complete or incomplete combustion)
PREPARATION
by oxidation of an aldehyde
ie.
-C
methanal
+
/2 O2
1
---->
-C
methanoic acid
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KETONE TYPE REACTIONS
1. Oxidations:
ketones + O2 ----> H2O + C &/or CO2
(complete or incomplete combustion)
PREPARATION
by oxidation of secondary alcohols (2°) by dehydration
ie.
-C-C-C-
+
/2 O2
----> - C - C - C -
1
2-propanal
+ H2O
propanone
ETHER TYPE REACTIONS
PREPARATION
by condensation (dehydration) of alcohols
ie.
- C - C - OH + HO - C - C -
---------->
- C - C - O - C - C - + H2O
ethanol
ether
or
2 C2H5OH
---------->
C4H10O + H2O
AMINE TYPE REACTIONS
PREPARATION
by substitution;
alkyl halide + ammonia
ie.
- C - C - Br +
---->
N
---->
amine + H-halide
-C-C-N
+ HBr
ESTERIFICATION: A TYPE REACTION
Esterification is the reaction between an organic acid and an alcohol to produce an ester,
which is an organic salt, and water.
CH3COOH + C2H5OH
ethanoic acid
(acetic acid)
+
ethanol
=
=
CH3COOC2H5 + H2O
ethyl ethanoate
(ethyl acetate)
+
water
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AMIDE TYPE REACTIONS
PREPARATION
1. carboxylic acid + ammonia
ie.
R - COOH + NH3 ---->
ie.
-C
+ N
---->
methanoic acid
(formic acid)
R - CONH2 + H2O
-C
+ H2O
methanoamide
(formamide)
2. ester + ammonia
ie.
-C-C
+
N
methyl ethanoate
(methyl acetate)
---->
-C-C
ethanoamide
(acetamide)
+
- C - OH
methanol
3. ester + amine
ie.
-C-C
methyl ethanoate
(methyl acetate)
+
-C-C-N
ethylamine
---->
-C-C
+
ethylethanoamide
- C - OH
methanol
CYCLIC COMPOUNDS TYPE REACTIONS
Cyclic organics form a ring in which all the carbon atoms are bonded together.
example;
AROMATIC COMPOUNDS TYPE REACTIONS
ie. benzene; C6H6
For
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ORGANIC CHEMISTRY: TYPE REACTIONS
1. Oxidation: Combustion or burning.
a)
Complete:
b)
Incomplete:
b)
hydrocarbon + O2 ----> CO2 + H2O
hydrocarbon + O2 ---->
C + H2O
or C + CO2 + H2O
Other Oxidations:
primary alcohols (1°) + O2 ----> aldehydes
secondary alcohols (2°) + O2 ----> ketones
+ H2O
aldehyde + O2 ----> carboxylic acid
carboxylic acid + O2 ----> H2O + C &/or CO2
(complete or incomplete combustion)
ketones + O2 ----> H2O + C &/or CO2
(complete or incomplete combustion)
2. Substitution: substituting for hydrogen.
a) C2H6 + Br2 ----> C2H4Br2 + H2
b) alkyl halide + ammonia
ie.
- C - C - Br +
3. Additions:
N
amine + H-halide
---->
-C-C-N
+ HBr
There are four types, all easy, because all involve the breaking of the double
bond (or triple bond) which is not difficult.
a)
Hydrogenation:
b)
Halogenation:
c)
Hydrolysis:
d)
---->
Self-Addition (Polymerization):
1st stage
2nd stage
many stages
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4. Dehydrogenation:
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Removing hydrogen usually forms unsaturated hydrocarbons.
5. Hydrolysis:
ie.
alkene + water ----> alcohol
ie.
C
C
+ H2O
---->
- C - C - OH
5. Condensation: sometimes called dehydration reactions. Can be part of Condensation
polymerization reactions.
ie.
- C - C - OH + HO - C - C -
---------->
ethanol
- C - C - O - C - C - + H2O
ether
or
2 C2H5OH
---------->
C4H10O + H2O
ester
water
6. Esterification:
carboxylic acid + alcohol
=
+
7. Preparation of Amides:
a)
ie.
ie.
carboxylic acid + ammonia
R - COOH + NH3 ----> R - CONH2 + H2O
-C
+ N
---->
methanoic acid
(formic acid)
b)
ie.
ie.
+ H2O
methanoamide
(formamide)
ester + ammonia
-C-C
+
methyl ethanoate
(methyl acetate)
c)
-C
N
---->
-C-C
ethanoamide
(acetamide)
+
- C - OH
methanol
ester + amine
-C-C
methyl ethanoate
(methyl acetate)
+
-C-C-N
ethylamine
---->
-C-C
ethylethanoamide
+
methanol
- C - OH
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