introduction to organic chemistry; saturated hydrocarbons
TRANSCRIPT
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INTRODUCTION TO ORGANIC CHEMISTRY; SATURATED HYDROCARBONS
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Organic Chemistry – science that deal generally with compounds of carbon
–fats, proteins, carbohydrates–fabrics–wood and paper products–plastics–medicinals
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Carbon atom is central to all organic compounds
What makes carbon special?
unique ability to bond to itself in long chains and rings;
ability to form strong covalent bonds with a variety of elements (H, O, N, S, P, halogens)
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Carbon atom: C atomic number 6
electron structure 1s22s22p2
stable isotopes 12C and 13C
carbon has several radioactive isotope
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Carbon has four valence electrons
1s2, 2s2, 2p2
C
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C
Carbon forms four single covalent bonds by sharing electrons with other atoms.
H
HH H
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CH
HH H
Carbon forms four single covalent bonds by sharing electrons with other atoms.
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A pair of electrons can be shared between two carbon atoms.
One covalent bond can be formed between two carbon atoms.
single bond
C C
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Single covalent bond can be formed between two carbon atoms C C
single bond
A dash represents a covalent bond.
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Two covalent bonds can be formed between two carbon atoms.
double bond
C C
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Two covalent bonds can be formed between two carbon atoms.
C Cdouble bond
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Three covalent bonds can be formed between two carbon atoms.
triple bond
C C
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Three covalent bonds can be formed between two carbon atoms.
C Ctriple bond
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Organic compound
s
Saturated (only single bonds)
Unsaturated (double or triple bonds)
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The types of molecular formulas and molecular models
H
H
H
H
C.... ....
C
H
HH
H
structural formula
C2H6
CH4
Lewis formul
a
molecular
formula
CH3CH3condensed structural formula
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CLASSES OF ORGANIC COMPOUNDS
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CLASSES OF ORGANIC COMPOUNDS (cont.)
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HYDROCARBONS
compounds that are composed only of carbon and hydrogen atoms bonded to each other by covalent bonds
Sources: fossil fuels - natural gas, petroleum, coal
Hydrocarbons
Aromatic (contain the benzene
ring)
Aliphatic (open-chain and
cyclic)
Alkanes Alkenes Alkynes
Cycloalkanes Cycloalkenes UNSATURATED
SA
TU
RA
TED
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ALKANES (paraffins, saturated hydrocarbons)straight or branched-chain hydrocarbons
with only single covalent bonds between the carbon atoms
Homologous series – each member of a series differs from the next member by a CH2 group.
General formula (for open chain alkanes): CnH2n+2; n – number of carbon atoms in the molecule
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ISOMERISM
Isomerism – phenomenon of two or more compounds to have the same molecular formula but different structural arrangement
Isomers – compounds that have the same molecular formula but different structural formulas
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C
H
HH
H
line structure form of
methane
CH4
space filling form of
methane
There is 1 possible structure for CH4.
19.419.4
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CH3CH3
line structure form of ethane
C
H
CH
H
H
H
H
space filling form of ethane
There is 1 possible structure for C2H6.
19.4
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line structure form of propane
C
H
CH
H
C
H
H
H
H
H
space filling form of propane
CH3CH2CH3
There is 1 possible structure for C3H8.
19.4
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C C CC
H
H
H H
H
HH
H
H
H
line structure form of butane
CH3CH2CH2CH3 space filling form of butane
There are 2 possible structures for C4H10
unbranched chain19.4
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C C C
C
H
H
H
H H
HH
H H
H
line structure form of 2-methyl
propane
CH2CHCH3
CH3
branched chain
space filling form of 2-methyl
propane
branched chain
There are 2 possible structures for C4H10.
19.4
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normal butane (n-butane) C4H10
2 –methyl propane
C4H10
C C CC
H
H
H H
H
HH
H
H
H
C C C
C
H
H
H
H H
HH
H H
H
m.p. –138.3oC
b.p. 0.5oC
m.p. –159.5oC
b.p. – -11.7oC
Normal butane and 2-methyl propane are isomers.
Isomers are compounds with the same molecular formula but different structural formulas.
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Pentane (C5H12) has 3 isomers.
This is the carbon skeleton with the longest continuous carbon chain. It is the first isomer of pentane.
C C C C C
n-pentane
C C C C C
H
H
H
H
H
H
HH
H
H
H
H
Hydrogen is added to each carbon to form four bonds.
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Pentane (C5H12) has 3 isomers.
2-methylpentane
To form the next isomer write a four carbon chain.
C C C CC C C C
C
Add the fifth carbon atom to either of the middle carbon atoms.
C C C C
C
Hydrogen is added to each carbon to form four bonds.
C C C C H
CH
H
H
H
HHH
H
H
H
H
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Pentane (C5H12) has 3 isomers.
2,2-dimethylpropane
To form the third isomer write a 3 carbon chain.
C C C
Add the remaining two carbon atoms to the central carbon atom.
C C C
C
C
Hydrogen is added to each carbon to form four bonds.
C C C
C
C
HHH
HHH
H
H
H
H
H
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SATURATED HYDROCARBONS
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NAMING ORGANIC COMPOUNDS
Used to: trivial names
Examples: wood alcohol – methanol; marsh gas – methane; alcohol or grain alcohol – ethanol; etc.
Now: internationally accepted and systematic method - IUPAC system (International Union of Pure and Applied Chemistry) - established in 1892
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ALKANES (CnH2n+2) ALKYL GROUPS (CnH2n+1)
Alkyl Groups
Alkyl group - derivative of corresponding alkane
The general formula: R = CnH2n+1. R – any alkyl group.
Alkyl group has 1 hydrogen atom less than the corresponding alkane.
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IUPAC RULES FOR NAMING ALKANES
1. The name of the compound consist of the name of the longest chain prefixed by the names of attached alkyl groups.
2. Select the longest chain.
3. Consider all alkyl groups attached to it.
4. Number the carbon atoms in the carbon chain starting from the end closest to the first carbon atom that has attached alkyl group.
5. Name each branch-chain alkyl group and designate its position by a number (3-methyl means a methyl group attached to carbon 3)
4. If the same alkyl groups occur more than once, indicate this by prefix (di-, tri-, tetra etc) (dimethyl indicates two methyl groups). The numbers indicating the positions of these alkyl groups are separated by comma, followed by a hyphen, and placed in front of the name (2,3-dimethyl).
5. When several alkyl groups are attached to the parent compound, list them in alphabetical order.
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1. Select the longest chain.
2. Consider all alkyl groups attached to it.
3. Number the carbon atoms in the carbon chain starting from the end closest to the first carbon atom that has attached alkyl group.
4. Name each branch-chain alkyl group and designate its position by a number (2-methyl means a methyl group attached to carbon 2)
Name the following compound
2-methylbutane
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Name the following compound
2-methylpentane
Each of the following formulas represent the same compound – 2-methypentane
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Name the following compound
2,3-dimethylbuthane
1. Select the longest chain.
2. Consider all alkyl groups attached to it.
3. Number the carbon atoms in the carbon chain starting from the end closest to the first carbon atom that has attached alkyl group.
4. Name each branch-chain alkyl group and designate its position by a number
5. If the same alkyl groups occur more than once, indicate this by prefix (di-, tri-, tetra etc) (dimethyl indicates two methyl groups). The numbers indicating the positions of these alkyl groups are separated by comma, followed by a hyphen, and placed in front of the name (2,3-dimethyl).
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Name the following compounds
2,2-dimethylbutane
2,4-dimethylhexane
H3
3-methylhexane
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Name the following compound
3-chloro- 4-ethyl-2,4-dimethyloctane
1. Select the longest chain.
2. Consider all alkyl groups attached to it.
3. Number the carbon atoms in the carbon chain starting from the end closest to the first carbon atom that has attached alkyl group.
4. Name each branch-chain alkyl group and designate its position by a number (3-methyl means a methyl group attached to carbon 3)
4. If the same alkyl groups occur more than once, indicate this by prefix (di-, tri-, tetra etc) (dimethyl indicates two methyl groups). The numbers indicating the positions of these alkyl groups are separated by comma, followed by a hyphen, and placed in front of the name (2,3-dimethyl).
5. When several alkyl groups are attached to the parent compound, list them in alphabetical order.
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2,2,4-trimethylpentane
2-methylhexane
5-ethyl-3-methyloctane
Name the following compounds
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H3C CH2CH C
CH3
CH3CH
CH3 CH3
CH2
Cl
Name the following compounds
CH3C CH2CH2CHCH3
CH2CH3CH2CH3
CH3
CH3
CH3CH3
CH3
CH2
CH CH
CH2
3,4-dimethylhexane
3-chloro-2,5,5-trimethylheptane
3,3,6-trimethyloctane
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Write the formula for:
CH3CH2
CH CH2 CH3
CH2
CH3
3-ethylpentane
3-bromo-5,6-diethyl-2,7-dimethyl-5-propylnonane
CH3CH CH CH2 C
CH2
CH3
CH CH CH2 CH3
CH2
CH3
CH3 CH3
CH2
CH2
CH3
Br
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Reactions of Carbon
1. Oxidation-reduction reactions
Oxidation of carbon compound
Reduction of carbon compound
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2. Substitution reactionIf in a reaction one atom in a molecule is exchanged by another atom or group of atoms
3. Elimination reactionIf a single reactant is split into two product, and one of the products is eliminated. Multiple bonds are formed
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4. Addition reaction
Two reactants adding together to form a single product. Reverse of an elimination reaction
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CH3CH2Cl H2O CH3CH2OH HCl+ +
Categorize each reaction
addition
substitution
elimination
CH3CH2CH2CH3CH3CH CHCH3
H2+
CH2 CH2 H2O CH3CH2OH+
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Reactions of alkanes
1. Combustion (with the production of large amount of heat energy)
Mechanical energy Electrical
energy
Combustion reactions are the most important for economics.
Combustion reactions are the most active reactions of alkanes.
In all other reactions alkanes are sluggish and demand activation (high temperature, catalists)
CH4(gas) + O2(gas) CO2(gas) + 2H2O + 191,8 kcalthermal energy
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2. Halogenation (a substitution reaction)
A halogen (Cl or Br) is substituted for a hydrogen atom in halogenation reactions.
CH3CH3 + Br2
CH3CH2Br + HBrbromoethane
CH3CH3 + Cl2 CH3CH2Cl + HClchloroethane
Alkylhalides are useful as intermediates for manufacturing of other substances
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3. Dehydrogenation (an elimination reactions)Alkanes lose hydrogen during dehydrogenation
4. Cracking
Breaking up large molecules to form smaller ones
C16H34 C8H18 + C8H16
alkane alkane alkene
propane
propeneCH3CH2CH3 CH3CH CH2
+ H2
Alkenes are formed (useful chemical intermediates)
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4. Isomerization (rearrangment of molecular structure)
CH3CH2CH2CH2CH3 CH3CH2CHCH3
CH3
catalist
, pressure
Halogenation reaction is used for production of petrochemicals (chemicals derived from petroleum and used for other purposes than fuel)
Dehydrogenation, cracking and isomerization reactions are used for production of motor fuels.
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Alkyl halides formation
CH4 + Cl2 CH3Cl + HClchloromethane
Reaction of methane with chlorine gives the mixture of mono-, di-, tri-, and tetrasubstituted chloromethanes
CH4 CH3Cl CH2Cl2 CHCl3 CCl4 + HClCl2 Cl2 Cl2 Cl2
The more chlorine the more CCl4.
chloro- methane
dichloro-methane
trichloro-methane
tetrachloro-methane
Monosubstitution product - one hydrogen atom is substitued by another atomDi-, tri, tetra- and so on substituted compounds – two, three, four hydrogen atom are substitued by another atoms
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CYCLOALKANES
Hydrocarbons
Aromatic (contain the benzene ring)
Aliphatic (open-chain and cyclic)
Alkanes Alkenes Alkynes
Cycloalkanes Cycloalkenes
Cycloalkanes (cycloparaffins, naphthenes) – cyclic, or close-chain, alkanes. Cycloalkanes are saturated hydrocarbons.General formula – CnH2n (two fewer hydrogen atoms than the corresponding open chain alkane)
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Add prefix cyclo to the name of alkane with the same number of carbon atom
Naming of Cycloalkanes
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UNSATURATED HYDROCARBONS
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UNSATURATED HYDROCARBONS
Widely used: polymers (plastic things); in medicine, cosmetics, perfumes, flavorings; detergents, insecticides, dyes.
Hydrocarbons
Aromatic (contain the benzene ring)
Aliphatic (open-chain and cyclic)
Alkanes Alkenes Alkynes
Cycloalkanes Cycloalkenes
Alkenes – double bond Alkynes – triple bond Aromatic – benzene ring
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Nomenclature of alkenes
1.Select the longest carbon-carbon chain containing the double bond
2.Name this compound as you would an alkane but change the –ane ending to –ene. Example: propane is changing to propene.
3.Number the carbon chain of compound starting with the end nearer to the double bound.
4.Place the number indicating the location of double bond in front of the alkene name (example: 3-propene)
5.Branch chains and other groups are treated as for alkanes.
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1-butene
2-butene
3-methyl-1-butene
3-propyl-1-hexene
Name the following compounds
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Write a structural formula for:
4-methyl-2-pentene
7-methyl-2-octene
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IMPORTANT: in naming of alkenes the double bond must be included in the chain even if there is longer chain in this compound
the longest carbon chain contains six carbons
We must include the double bond in the chain
the carbon chain containing the double bond has five carbons
2-ethyl-1-pentene
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Name the following compounds
3-methyl-2-pentene
2,4-dimethyl-2-pentene
2-methyl-1-butene
2-methyl-2-butene
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Name the following compounds
3-methyl-3-heptene
3-methyl-1-heptene
CH3 CH2
CH3
CH2
CHCH2C CH3
CH3 CH2
CH2
CH
CH2CH2CH CH3
CH3 CH2
CH2
CH2
CH
CH2CH2C CH3
CH3
3-ethyl-3-methyl-1-heptene
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Write a structural formula for:
4-chloro-5,6-diethyl-2,7-dimethyl-5-propyl-2-nonene
CH3C CH
CH3
CH
Cl
C
CH2
CH2
CH3
CH3
CH2
CH
CH3
CH2
CH
CH3
CH2CH3
4,5-dichloro-2,3-dimethyl-1-pentene
C CH
CH3
CH
Cl
CH2
CH3
CH2
Cl
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Nomenclature of alkenes containing more than one double
bondCompounds with two (di) double bounds are called dienes, with three (tri) – trienes.
1,4-pentadiene 2-methyl-1,3-butadiene
Name the following compounds
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Name the following compounds
C C C
Cl
CH2
CH3
CH
Cl
4,5-dichloro-3-methyl-1,2,4-pentatriene
5-methyl-4-pentyl-2,5-octadieneCH3
CH
CH
CH
CH3
CH2C
CH3
CH
CH2
CH3
CH2CH2
CH2
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Geometric Isomerism in Alkenes
1,2-dichloroethane
carbon atoms can rotate freely about the single bond
these two compounds are identical
carbon atom can not rotate about the double bond
Restricted rotation of carbon atom around the bond with other carbon atom results in the phenomenon known as geometric isomerism
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these compounds are different
cis-1,2-dichlorethene
trans-1,2-dichlorethene
Geometric isomers (cis-trans isomers) -compounds that differ from each other only in the geometry of their molecules and not in the order of their atoms
Cis- isomer has substituent groups on the same side of the double bond
Trans- isomer has substituent groups on the opposite sides of the double bond
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An alkene shows cis-trans isomerism when each carbon atom of the double bond has two different kinds of groups attached to it
cis-isomer
trans-isomer
An alkene doesn’t show cis-trans isomerism if one carbon atom of the double bond has two identical groups attached to it
C CAA
BBC C
A
A B
B
C CH
H
H
HC C
H
H
CH3
H
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cis-2-butene trans-2-butene
Write geometric isomers for: 2-butene
CH CH3CH3 CH
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Chemical properties of alkenesAddition
So far as alkenes have double bonds they are more reactive than alkanes and undergo addition reactions.
Some of the reagents that can be added to alkenes: hydrogen, halogens, hydrogen halides, water, sulfuric acid, etc.
C
C
Brown color of Br2 disappears in this reaction.
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As result of addition alkenes are converted to saturated molecules.
Addition reactions are reverse to the elimination reactions.
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Markovnikov’s rule
When an asymmetrical molecule HX (HCl) adds to a carbon-carbon double bond, the hydrogen from HX goes to the carbon atom that has the greater number of hydrogen atoms.
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Write the formulas for the organic compounds formed when 2-methyl-1-butene reacts with (a) H2, (b) Cl2, (c) HCl, (d) H2O
2-methyl-1-butene
(a)(b)
1,2-dichloro-2-methylbutane
(c) (d)
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Hydrocarbons
Aromatic (contain the benzene ring)
Aliphatic (open-chain and cyclic)
Alkanes Alkenes Alkynes
Cycloalkanes Cycloalkenes
Widely used: plastic things; in medicine, cosmetics, perfumes
Alkynes – unsaturated hydrocarbons containing triple bond
Alkynes
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Naming of alkynes1. Select the longest carbon-carbon chain containing the
triple bond.
2. Name this compound as for alkene but change the –ene ending to –yne.
3. Number the carbon chain of compound starting with the end nearer to the triple bound.
4. Place the number indicating the location of triple bond in front of the alkyne name (example: 3-propyne)
5. Branch chains and other groups are treated as for alkanes.
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Chemical propertiesAddition Reactions
Positive Bayer’s test with potassium permanganate (disappearance of purple-pink color)
Reactions with halogens. Either one or two molecules of halogens can be added.
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Reactions with hydrogen halides.
Vinyl chloride is widely used in chemical industry, for example for production of plastic polyvinyl chloride
This reaction follows Markovnikov’s rule.
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These reactions follow Markovnikov’s rule.
Acetylene is the most important industrially.
Many different polymers are manufactured from acetylene (production of clothes, superabsorbents (disposable diapers, soil additives))
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Aromatic hydrocarbonsStructure
Benzene and its derivatives are classified as aromatic hydrocarbons.
Kekule’s formula:
carbon atoms in a benzene molecule are arranged in a six-membered ring with one hydrogen atom bonded to each carbon atom and with three double carbon-carbon bonds.
Molecular formula of benzene: C6H6
Benzene doesn’t react as a typical alkene (doesn’t decolorize bromine solution, negative Bayer’s test). Benzene behaves chemically like a typical alkane (substitution reactions).
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Structure of benzene can be represent by different formulas
Kekule structures
Kekule formulas are classical however such structures actually doesn’t exist
Formulas C or D more accurately represent the real benzene structure
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Naming of aromatic compoundsMonosubstituted
benzenes
1.Add the name of a substitutent group as a prefix to the word benzene
2.Write the name as one word
3.Position of substituent is not important
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F
CH2CH2CH3
OHCH2CH3
Name the following compounds:
fluorobenzene
propylbenzene
ethylbenzene hydroxybenzene
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Some monosubstituted benzenes have special (trivial) names. These names should be memorize.
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The group (C6H5) is called phenyl group
The name phenyl can be used to name compounds that can not easily be named as benzene derivatives
3-chloro-2-phenylpentane
diphenylmethane
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Disubstituted BenzenesIn disubstituted benzenes the prefixes
ortho-, meta- and para- (o-, m-, p-) are used for naming.
In ortho- disubstituted compounds, the two substituents are located on adjacent carbon atoms
In meta- disubstituted compounds, the two substituents are one carbon apart
In para- disubstituted compounds, the two substituents are located on opposite points of ring
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ortho-dichlorobenzene
Name the following compounds:
meta-dichlorobenzene para-dichlorobenzene
CH2CH3
CH2CH3
CH2CH3
CH2CH3
CH2CH3
CH2CH3
ortho-diethylbenzene meta-diethylbenzene
para-diethylbenzene
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When the two substituents are different the names of two substituents are given in alphabetical order
o-bromochlorobenzene
m-ethylnitrobenzene
CH2CH3
CH3
CH2CH3
CH2CH2CH2CH3
p-ethylmethylbenzene
o-butylethylbenzene
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Sources and using of aromatic hydrocarbons
Sources:
Coal tar (by-product of the manufacture of coke)
Alkanes found in petroleum
Using: in the production of - drugs, - dyes, - detergents, - explosives, - insecticides, - plastics, - synthetic rubber.
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ALCOHOLS
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Alcohols – a class of compounds containing the hydroxyl (-OH) functional group
General formula – ROH
Alcohols are derived from aliphatic hydrocarbons by the replacement of at least one hydrogen atom with a hydroxyl group
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Classification of AlcoholsPrimary – carbon atom to which the –OH group
is attached is directly bonded to one other carbon atom
Secondary – carbon atom to which the –OH group is attached is directly bonded to two other carbon atom
Tertiary – carbon atom to which the –OH group is attached is directly bonded to three other carbon atom
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If two or more –OH groups are attached to the same carbon atom such compound is not stable
If two or more –OH groups are attached to the different carbon atoms such compounds is stable
polyhydroxy alcohols
monohydroxy-, dihydroxy-, trihydroxy-, tetrahydroxy-, and so on.
Alcohols can be also classified as
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The formulas of alcohol can be written as follow:
or
2-butanol
2-butanol
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Naming of alcohols
1.Select the longest chain of carbon atoms containing the hydroxyl groups
2.Number the carbon atoms in this chain so that the one bearing the –OH group has the lowest possible number
3.Form the parent alcohol name by replacing the final –e of alkane by –ol.
4.Locate the position of the –OH by placing the number of corresponding carbon atom before the alcohol name.
5.Name each side chain and designate its position by number
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Name the alcohol CH3CH2CH2CH2OH
1. The longest carbon chain has 4 carbons
2. Number the carbon atoms (carbon bonded to –OH must have number 1)
3. Four carbon alkane is called butane. Change –e to –ol butanol
4. OH group is on carbon 1, so place 1 before butanol
Result: 1-butanol
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Name the following compounds
1-propanol
2-propanol cyclohexanol
3-methyl-1-butanol 4-methyl-2-hexanol
2-ethyl-1-pentanol 5-bromo-5-methyl-3-hexanol
CH3 CH2CH2
OH CH3 CH CH3
OH
OH
CH3 CH CH2
CH3
CH2OH CH3CH2CHCH2CHCH3
CH3OH
CH3CH2CHCH2CH2CH3
CH2OHCH3CH2CHCH2CCH3
OH CH3
Br
OH
CH33-methylcyclopentanol
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Write the structural formulas for:
3,3-dimethyl-2-hexanol
CH3
CH3
OH
CH3CH C CH2CH2CH3
OH
CH3
Cl
2-chloro-4-methylcyclopentanol
CH2CH2
CH CH3
OH
4-phenyl-2-butanol
OH
ClCl
Cl
2,3,4-trichlorocyclobutanol
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Nomenclature of alkohols containing more than one -OH
groupsCompounds with two (di) –OH groups are called diols, with three (tri) – triols.
Name the following compounds
1,3-cyclohexanediol
1,2-ethanediol
HOCH2 CH2OH
OH
OH
OH OH
CH2CHCH2
OH1,2,3-propanetriol
CH3CH3CH
CH2OH
CHOH CHOH CH
CH2CH3
2,5-dimethyl-1,3,4-heptanetriol
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relatively high boiling point (depends on the hydrogen bonding between alcohol molecules)
alcohols containing up to three carbon atom are soluble in water (solubility depends on hydrogen bonding between alcohol molecules and water)
alcohols with 5-11 carbons are oily liquids, 12 or more carbon atoms – waxlike solids
two or more –OH groups increase boiling point and solubility
Alcohols:
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Chemical properties of alcohols
Acidic and basis properties (similar to water properties)
a) In acidic solution alcohols accept a proton
oxonium ion (protonated alcohol)
b) Alcohols react with alkali metals to release hydrogen
alkoxide ion (strong base)
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1. OxidationThe hydroxyl group gives an alcohol the capability of forming an aldehide, ketone or carboxylic acid
Tertiary alcohols don’t have a hydrogen on the –OH carbon and can not react with oxidizing agents
Oxidation occurs at the carbon atom bonded to the –OH group and this atom becomes an aldehyde or carboxylic acid. The rest of the molecule remains the same.
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Oxidation of ethanol in organism (in liver)
Toxic compound, can cause the liver damage (liver
cirrhosis)
Can be used as sourse of energy for the organism
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2. Dehydration (elimination of water)
a. Intramolecular dehydration (the alkenes are formed)
Saytzeff’s rule. If there is the choice of positions for double bond the preferred location is the one that gives the more highly substituted alkene – that is, the alkene with the most alkyl groups attached to double-bond carbons.
Remove the hydrogen from the carbon with fewer hydrogen.
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b. Intermolecular dehydration (the ethers are formed)
This type of reaction occurs only between primary alcohols.
Such type of reactions is called condensation reaction (two molecules are combined with removing of small molecule).
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3. Esterification (convertion of alcohols to esters)Alcohol reacts with carboxylic acid to form an ester and water.
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Utility of the Hydroxyl Group
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Common AlcoholsMethanol (wood alcohol)
Preparation: - heating of wood to high temperature without oxygen (distructive distillation) - hydrogenation of carbon monoxide under the high pressure
methanol
Physical properties:
highly flammable liquid
poisonous, can cause blindness and death
Using: -convertion to formaldehyde –manufacture of esters and other chemicals –production of denaturing ethyl alcohol -industrial solvent
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Ethanol (ethyl alcohol, spirit)Preparation:
-fermentation. Starch is converted to sugar, then sugar is converted to ethanol. The enzymes of yeast are used.
-acid-catalyzed addition of water to ethylene (ethylene can be obtain from petroleum)
Using: -intermediate in the production of other chemicals -solvent for many organic substances -ingredient for pharmaceutical, perfumes, flavorings -ingredient of alcoholic beverages
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Glycerol (1,2,3-propanetriol, glycerine)Contains three –OH groups.
Physical properties: -liquid with a sweet, warm taste -hygroscopic (is able to hold water molecules by hydrogen bonding)
Preparation: -by-product of processing fats to make soap and other products -it is synthesized from propene
Using: -manufacturing of polymers -manufacturing of explosives -emollient in cosmetics
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ETHERSGeneral formula R-O-R’.
R and R’ can be saturated, unsaturated or aromatic hydrocarbons. R and R’ can be alike or different.
Naming ethers
A. Common names (only for naming simple ethers)
Common names are formed from the names of groups attached to oxygen atom
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O
Name the following compounds using common names
diethyl ether; ethyl ether or ether
CH3CH2-O-CH2CH3
diphenyl ether
OCH3
methyl phenyl ether
CH3CH2CH2O CH2CH2CH2CH3
butyl propyl ether
CH3CH2O CHCH3
CH3
ethyl isopropyl ether
OCH2 CH CH CH2
divinyl ether
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B. Naming according to IUPAC system
Alkoxy group is named by dropping the ending –yl of the alkyl name and adding the suffix –oxy.
Examples:
CH3O-, alkyl is called methyl, replace ending –yl to –oxy. Group is called methoxy. CH3CH2O- - is called ethoxy (eth + oxy).
- is called phenoxy (phen + oxy).
Group R-O- is called alkoxy group (consist of alkyl group R- and oxygen atom).
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Rules for naming ethers
1. Select the longest carbon chain and label it with the name of corresponding alkane.
2. Change the –yl ending of other hydrocarbon group to –oxy.
3. Combine the two names giving the alkoxy name and its position on the longest carbon chain first.
metoxyethane
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O
CH3CH2-O-CH2CH3
OCH3
CH3CH2CH2O CH2CH2CH2CH3
CH3CH2O CHCH3
CH3
Name the following compounds
ethoxyethane
methoxybenzene
phenoxybenzene
1-propoxybutane
CH3CH2CH2O CHCH2CH3
CH3
2-propoxybutane
2-ethoxypropane
CH3
CH3CH2CH2CH2 O CHCH2CH3
CH2
3-butoxypentane
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Name the following compounds
O CH2CHCH3CH3
CH3
1-methoxy-2-methylpropane
OCH3
Clm-chloromethoxybenzene
OCH2CH2CH3
ClCl
1,2-dichloro-4-propoxybenzene
CH3CH
CH3
O CHCH2CHCH3
CH3 CH3
2-isopropoxy-4-
methylpentane
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Physical Properties of EthersThe shape of molecule is similar to water and alcohol molecules
Ethers are more polar than alkanes (alkanes don’t conatain oxygen atom) Ethers are less polar than alcohols or water (ethers don’t contain hydrogen)
Ethers form hydrogen bonds with water molecules or acids
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Ethers – very good solvents for organic compounds
Some polar compounds (water, alcohols) can be dissolve to some extent in ethers
Ethers are highly flammable
Vapors can form with air explosive mixture
Ethers with long carbon chain are insoluble in water
Ethers with small carbon chain are very little soluble in water and acids
Solubility and boiling point of ethers depend on the carbon chain structure
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Ethers have little chemical reactivity
Ethers can slowly react with oxygen from air to form peroxides (explosive substances).
Chemical Properties
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Preparation of ethers
1. Intermolecular dehydration of alcohols
2. Williamson synthesis. Alkyl halides react with sodium alkoxides or sodium phenoxides to form ethers. This is the substitution reaction.
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ThiolsThiols (mercaptants) – organic compounds containing –SH group.
Naming of thiols
The principle of naming is as for alcohols but except the ending –ol the ending –thiol is used.
CH3SH CH3CH2CHCH3
SHmethanethiol
2-butanethiol
CH3
CH3CH2CHCHCH2CH3
SH
4-methyl-3-hexanethiolSH
cyclohexanethiol
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Properties
1. Foul odours (natural gas is odorized by methanethiol to be detectable)
2. Oxidation to disulfides
FunctionsDisulfide structures in proteins. Constituent of coenzyme A (metabolism).
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ALDEHYDES AND KETONESALDEHYDES AND KETONES
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Structure of aldehydes and ketones
C OBoth aldehydes and ketones contain carbonyl group
Differerence: -aldehydes contain hydrogen atom bounded to carbonyl group -ketones have only alkyl or aromatic groups attached to carbonyl group
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Methanal is the smallest aldehyde (the first member from the homologous series)
Ethanal is the second member of the homologous series
methyl group on 4 carbon
the longest chain is hexane
4-methylhexanal
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Name the following compound
OCH3CH2CH2CH2C
Hpentanal
OCH2ClCHCH2CH2C
H
CH3
5-chloro-4-methylpentanal
O
HCCH2CHCH2CHCH3
OH OH
3,5-dihydroxyhexanal
O
HCH CHC
3-phenyl-2-propenal
O
CH3
HCHCHC
CH2CH3
2-methyl-3-phenylpentanal
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Naming of Ketones
1.Select the longest chain containing the ketone group.
2.Drop the ending –e from the corresponding alkane name and add the suffix –one.
3.If the chain is longer than four carbons, it is numbered so that the carbonyl group has the lowest number possible. This number is prefixed to the parent name of the ketone.
4.Name other groups attached to parent chain as usual.
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Name the following compounds
CH3 C CH3
O
CH3 C CH3
O
CH2 CH3 C CH3
O
CH2 CH2
propanone
butanone
2-pentanone
CH3 C CH3
O
CH CH2CH2
CH3
4-methyl-3-hexenone
CH3
CH3
CHCH
C O
CH3
OH4-hydroxy-3-methyl-2-pentanone
O
cyclohexanone
O
CH3
CH3
CH32,4,6-trimethylcyclohexanone
CH2 CH2 CCH2CH2OH
O
1-hydroxy-5-phenyl- 2-pentanone
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Alternative Names of KetonesIt is used to name simple ketones.List the names of the alkyl or aromatic groups attached to carbonyl carbon together with the word ketone.
methyl ethyl ketone (butanone)
methyl methyl ketone (propanone)
Propanone and butanone are the most widely used ketones. They have the special (common) names: acetone (propanone) and MEK (butanone).
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Name the following compounds
C
O
CH3CH2CH2CH3
ethyl ethyl ketone (diethyl ketone) CH3
CH3
C
O
CH3CH2CH
ethyl isopropyl ketone
C
O
dicyclohexyl ketone
CH3
C
O
CHCH
CH3
CH3
CH3
diisopropyl ketone
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Naming of Aromatic KetonesAromatic ketones are named similarly to the aliphatic ketones and can have the special names as well.
C
O
CH3
1-phenylethanone (methyl phenyl ketone)
C
O
CH3CH2
1-phenyl-1-propanone (ethyl phenyl ketone)
2-methyl-1-phenyl-1-butanone
C
O
CH3CH2CH
CH3
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Cinnamaldehyde (oil of cinamon)
Benzaldehyde (oil of bitter almonds)
Naturally occurring aldehydes and ketonesMany aldehydes have a specific odour and can be used in flavoring and perfumes
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Carvone (chief component of spearmint oil)
Muscone (gland of male musk deer, used in perfumes)
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Civetone (secretion of the civet cat, used in perfumes)
Camphor (from the camphor tree)
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Cortisone (hormone; produced by epinephrine glands; regulate metabolism in organism; widely used in medicine)
Glucose Ribose Fructose
Sugars; energetic and plastic material for organism
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Citral (oil of lemon)
Vitamin K (antihemorrhagic vitamin)
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Chemical Properties of Aldehydes and Ketones
C OChemical properties of aldehydes and ketones are determined by the functional carbonyl group
1. OxidationsAldehydes are oxidized to carboxylic acids by different agents (K2Cr2O7+H2SO4; Ag+; Cu2+; oxygen of air)
Ketones are not oxidized by such agents. Ketones can be oxidized under drastic conditions (hot potassium permanganate). Carbon-carbon bonds are broken under these conditions and variety of products are formed.
orange green
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The Tollens test (silver-mirror test)Silver ions oxidizes ammonia (Tollens’ reagent is
formed) Ag+ ions are reduced to metallic silver by aldehydes
Add into tube aldehyde, silver nitrate and ammonia
The silver mirror appears on the inner wall of the tube
CH3 C
O
H Ag(NH3)2OH AgCH3 C
O
ONH4 NH3+ + + +2 2 H2O
Tollens’ Reagent
3
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Fehling testFehling solutions contain Cu2+ ions in alkaline medium. Cu2+ has blue color. During reaction it is reduced and brick-red copper oxide is formed.
Before reaction (blue color of Cu2+)
After reaction (brick-red color of Cu2O)
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Ketones don’t give a positive Tollens or Fehling tests
Tollens or Fehling test can be used to distinguish between aldehydes and ketones
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2. Reduction
Aldehydes and ketones are reduced to alcoholsReducing agents: -hydrogen (catalyst Ni); -litium aluminium hydride (LiAlH4); -sodium borohydride (NaBH4).Aldehydes yield primary alcohols; ketones yield secondary alcohols
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Common Aldehydes and KetonesFormaldehyde
(methanal)Can be obtained in the oxidation of methanol by oxygen (silver or copper are catalysts)
Properties: -gas -poisonous -very irritating (ingestion can cause death) -soluble in water -37 % solution of formaldehyde is called formalin
Using:
manufacture of polymers;
preservation of biological specimens
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Acetaldehyde (ethanal)
Can be obtained in the oxidation of ethanol
Volatile liquid with pungent odorUsing: intermediate in the production of other chemicals (for example, acetic acid)
Three or four molecules of ethanal can polymeraze to form cyclic compounds paraldehyde and metaldehyde, which can be used for production of sedative drugs and pesticides
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Acetone (methyl methyl ketone) and MEK (methyl ethyl ketone)
Using: solvents, manufacturing of drugs, chemicals, explosives, in plastic industry; for removal of paints
Acetone and MEK can be obtained by oxidation of secondary alcohols:
Acetone is formed in human body In some diseases (diabetes mellitus, starvation) the concentration of acetone is increased in blood and urine.