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ORGANIC CHEMISTRY
Organic chemistry: -The branch of chemistry that deals with carbons compounds. Organic derived from living organisms Study of compounds extracted from living organisms and their natural products. Examples: sugar, starch, urea, waxes, carbohydrates, fats and etc
Human are composed of organic molecules proteins in skin, lipid in cell membranes, glycogen in livers and the DNA in the nuclei of cells.
Chemistry of carbon: - Two stable isotops (13C and 12C) - electron configuration: 1s2 2s2 2p2 - four valence electrons - can form more compounds than any other element - able to form single, double and triple carboncarbon bonds, and to link up with each other in chains and ring structures
Functional group: A group of atoms that is largely responsible for the chemical behavior of the parent molecule. Functional groups: - hydrocarbons - alcohols - aldehydes - ketones - carboxylic acids - alkyl halides
HYDROCARBONS
Made up of only hydrogen and carbon
ALKANES
General formula: CnH2n+2, where n = 1, 2, . Only single covalent bonds are present Known as saturated hydrocarbons because contain the maximum number of hydrogen atoms that can bond with the number of carbon atoms present. Can be assumed to be sp3-hydridized
The melting and boiling points of the straight-chain isomers of the first 10 alkanes
Homologous Series
1.
2. 3.
Definition: A series of compounds in which each member differs from the next by a specific number and kind of atoms. Alkanes: Differ only at number of (CH2) Series of compounds that has the same functional group.
NAMING ALKANES
Alkyl groups are used to name organic compounds. The general formula of an alkyl group is CnH2n+1. The letter R is often used in formulas to represent any of the possible alkyl groups. R= CnH2n+1 (any alkyl group) R = CH3 methyl group R = CH3CH2 ethyl group
IUPAC RULES International Union of Pure and Applied Chemistry RULE 1. Select the longest continuous chain of carbon atoms as the parent compound.
Consider all alkyl groups attached to it as branch chains or substituents that have replaced hydrogen atoms of the parent hydrocarbon. If two chains of equal length are found, use the chain that has the larger number of substituents attached to it. The alkanes name consists of the parent compounds name prefixed by the names of the alkyl groups attached to it.
CH3
CH2
CH CH3
CH2
CH2
CH3
CH3
CH2
CH CH3
4
CH2
CH2
CH3
1 CH3
2 CH2
3 CH
4 CH2
5 CH2
6 CH3
CH3
1 CH3
2 CH2
3 CH
4 CH2
5 CH2
6 CH3
CH3
This is a methyl group.
It is a branch chain and can be considered to have replaced a hydrogen on the parent compound.
1 CH3
2 CH2
3 CH
4 CH2
5 CH2
6 CH3
CH3
The name of the compound is 3 3-methylhexane.
IUPAC RULES
RULE 2. Number the carbon atoms in the parent carbon chain starting from the end closest to the first carbon atom that has an alkyl group substituted for a hydrogen atom.
If the first subsitutent from each end is on the samenumbered carbon, go to the next substituent to determine which end of the the chain to start numbering.
1 2
isopropyl group
If the chain is numbered right to left, the isopropyl group is on carbon 4. Use right to left numbering so that the isopropyl group is on the lowest numbered carbon.
4-isopropyloctane
8 7
isopropyl group
IUPAC RULES
RULE 3. Name each alkyl group and designate its position on the parent carbon chain by a number (e.g., 2-methyl means group attached to C-2).
2-isopropyl pentane
RULE 4. When the same alkyl-group branch chain appears more than once, indicate this repetition by a prefix (di-, tri-, tetra- and so forth) written in front of the alkyl group name (e.g. dimethyl indicates two methyl groups).
The numbers indicating the alkyl-group positions are separated by a command and followed by a hyphen and are placed in front of the name (e.g., 2,3-dimethyl).
2,3-dimethylpentane
RULE 5. When several different alkyl groups are attached to the parent compound, list them in alphabetical order (e.g. ethyl before methyl in 3-ethyl-4-methyloctane). Prefixes are not included in alphabetical ordering (ethyl comes before dimethyl).
methyl
ethyl
3-ethyl-4-methyloctane
NO2 Br
1
CH3 CH
CH
CH3
CH3
3-bromo-2-nitropentane
CYCLIC HYDROCARBONS
A hydrocarbon that contains carbon atoms joined to form a ring. Cycloalkanes all carbons of the ring are saturated
cyclopropane
cyclobutane
cyclopentane
cyclohexane
butane
cyclopentane
cyclohexane
NOMENCLATURE OF CYCLOALKANES
CH3
= methylcyclopentane
CH3
4 32 5 61
CH2CH3
1-ethyl-3-methylcyclohexane
ISOMERISATION
-
Structural isomers: Molecules that have the same molecular formula, but different structure
Propane
Butane Pentane Hexane Heptane Octane Nonane
C3H8
C4H10 C5H12 C6H14 C7H16 C8H18 C9H20
1
2 3 5 9 18 35
Decane
C10H22
75
ALKENES
Also called olefins Contain at least one carbon-carbon double bond (C=C) General formula, CnH2n (n=2,3,) Classified as unsaturated hydrocarbons (compound with double or triple carbon-carbon bonds that enable them to add hydrogen atoms. sp2-hybridized For example: C2H4 - ethylene
CH2
CH2
ALKYNES
Alkynes contain at least carbon-carbon triple bond. General formula: CnH2n-2, where n = 2, 3,. Alkyne nomenclature: Used suffix yne Same as alkene nomenclature
1 2 3 4 1
HC
CH2CH3
H3C
CH3
1-butyne
2-butyne
IUPAC RULES
RULE 1. Select the longest continuous carbon chain that contains a double or triple bond.
RULE 2. Name this compound as you would an alkane, but change ane to ene for an alkene and to yne for an alkyne.
Name This isthe theparent longest continuous octene. compound chain. Select it as the parent compound.
RULE 2. Name this compound as you would an alkane, but change ane to ene for an alkene and to yne for an alkyne.
This chain contains a triple bond. Name the parent compound octyne.
RULE 3. Number the carbon chain of the parent compound starting with the end nearer to the double or triple bond. Use the smaller of the two numbers on the double- or triple-bonded carbon to indicate the position of the double or triple bond. Place this number in front of the alkene or alkyne name.
IUPAC RULES
This end of the chain is closest to the double bond. Begin numbering here.
IUPAC RULES
The name of the parent compound is 1-octene. 4 3 2 1
5 6
7
8
IUPAC RULES
The name of the parent compound is 1-octyne. 4 3 2 1
5 6
7
8
RULE 4. Branched chains and other groups are treated as in naming alkanes. Name the substituent group, and designate its position on the parent chain with a number.
IUPAC RULES
The is attached to carbon 4. Thisethyl is an group ethyl group.
4 3 2 1
5 6
4-ethyl-1-octene
7
8
IUPAC RULES
The ethyl group is attached to carbon 4.
4 3 2 1
5 6
4-ethyl-1-octyne
7
8
4-methyl-cis-2-pentene
cis two particular atoms (or groups of atoms) are adjacent to each other trans the two atoms (or groups of atoms) are across from each other
CYCLOALKENES
cyclopropene
cyclobutene
cyclopentene
cyclohexene
Nomenclature of cycloalkenes: Similar to that alkenes Carbons atoms in the double bond are designated C1 and C2
6 5 4 3 1 2
CH3
5 4 3 1 2
1-methylcyclohexene
1,5-dimethylcyclopentene
AROMATIC HYDROCARBONS
benzene ring
A substituted benzene is derived by replacing one or more of benzenes hydrogen atoms with an atom or group of atoms. A monosubstituted benzene has the formula C6H5G where G is the group that replaces a hydrogen atom.
Monosubstituted Benzenes
Some monosubstituted benzenes are named by adding the name of the substituent group as a prefix to the word benzene. The name is written as one word.
nitro group ethyl group
nitrobenzene
ethylbenzene
Certain monosubstituted benzenes have special names. These are parent names for further substituted compounds.
methyl group
hydroxy group
toluene
phenol
carboxyl group
benzoic acid
amino group
aniline
C6H5 is the phenyl group. It is used to name compounds that cannot be easily named as benzene derivatives.
CH3CH=CHCHCH3
diphenylmethane
4-phenyl-2-pentene
Disubstituted Benzenes
Three isomers are possible when two substituents replace hydrogen in a benzene molecule.
The prefixes ortho-, meta- and para- (o-, mand p-) are used to name these disubstituted benzenes.
para disubstituted benzene substituents are on opposite sides of the benzene ring
When one substituent corresponds to a monosubstituted benzene with a special name, the monosubstituted compound becomes the parent name for the disubstituted compound.
phenol
m-nitrophenol
When one substituent corresponds to a monosubstituted benzene with a special name, the monosubstituted compound becomes the parent name for the disubstituted compound.
toluene
m-nitrotoluene
When a benzene ring has three or more substituents, the carbon atoms in the ring are numbered.
Numbering starts at one of the substituent groups. The numbering direction can be clockwise or counterclockwise. Numbering must be in the direction that gives the substituent groups the lowest numbers.
clockwise numbering
6-chloro
1-chloro
6 5
4-chloro
4 3
1,4,6-trichlorobenzene
2-chloro
1-chloro
2
4-chloro
4 5
1,2,4-trichlorobenzene
When a compound is named as a derivative of the special parent compound, the substituent of the parent compound is considered to be C-1 of the ring.
1 1 6 5 4 2
2
3 4
2,4,6trinitrotoluene (TNT)
toluene
ALCOHOLS
OH
Phenols: Compounds with hydroxyl group bonded directly to an aromatic (benzene) ring.
OH
CLASSIFICATION
OH
Classes: i) Primary alcohol - -OH group attached to a primary carbon atom ii) Secondary alcohol - -OH group attached to a secondary carbon atom iii) Tertiary alcohol - -OH group attached to a tertiary carbon atom
TYPE
i)
STRUCTURE
H R C H
EXAMPLES
CH3
Primary (1)
OH
CH3CH2-OH ethanol
CH3CHCH2 OH 2-methyl-1-propanol
ii)
Secondary (2)
R' R C OH H
OH cyclohexanol
iii)
Tertiary (3)
R' R C OH R''
Polyhydroxy Alcohols
Alcohols that contain more than one OH group attached to different carbons are called polyhydroxy alcohols.
Naming Alcohols
IUPAC RULES
1.
2.
3.
4.
Select the longest continuous chain of carbon atoms containing the hydroxyl group. Number the carbon atoms in this chain so that the one bonded to the OH group has the lowest possible number. Form the parent alcohol name by replacing the final e of the corresponding alkane name by ol. When isomers are possible, locate the position of the OH by placing the number (hyphenated) of the carbon atom to which the OH is bonded immediately before the parent alcohol name. Name each alkyl branch chain (or other group) and designate its position by number.
This is the longest continuous chain that contains an hydroxy group. Select this chain as the parent compound.
4 3 2 1
This end of the chain is closest to the OH. Begin numbering here.
4 3 2 1
3-methyl-2-butanol
This is the longest continuous chain that contains an hydroxy group. Select this chain as the parent compound.
3
2 1
This end of the chain is closest to the OH. Begin numbering here.
3
2 1
3-methyl-2-pentanol
EXAMPLE
CH3 OH
4 3
CH3
CH
CH2
Br
CH3
1) Longest carbon chain = 4 carbons = root name: butanol 2) Position of OH group = second carbon atom = 2-butanol 3) Name of substituents = 1-bromo = 3-methyl = 3-methyl COMPLETE IUPAC NAME = 1-bromo-3,3-dimethyl-2-butanol
CH2 CH2 OH OH
1,2-ethanediol
CH2 CH CH2 OH OH OH
1,2,3-propanetriol
Ethers
An ether has the formula ROR. R and R can be the same or different groups. R and R can be saturated, unsaturated or aromatic. Saturated ethers have little chemical reactivity but are often used as solvents.
Alcohols and ethers are isomeric. They have the same molecular formula but different structural formulas.
An alcohol and its isomeric ether have different chemical and physical properties.
C2H6O
CH3CH2OH
ethanol B.P. 78.3oC hydrogen bonds soluble in water
C2H6O
CH3OCH3
dimethyl ether B.P. 27.3oC does not hydrogen bond insoluble in water
Naming Ethers
Common Names
Common names of ethers are formed from the names of the groups attached to the carbon atom in alphabetical order followed by the word ether.
CH3CH2CH2 O CH2CH3
propyl ether ethyl ethyl propyl ether
IUPAC RULES
RO is an alkoxy group. Ethers are named as alkoxy derivatives of the longest carbon-carbon chain in the molecule
IUPAC RULES
Select the longest carbon-carbon chain and label it with the name of the corresponding alkane.
1.
2.
Change the yl ending of the other hydrocarbon group to oxy to obtain the alkoxy group name. Combine the names from steps 1 and 2, giving the alkoxy name first, to form the ether name.
3.
This is the longest carbon-carbon chain. Label it the Change with name the name of the of other the corresponding hydrocarbon alkane. group to oxy.
CH3CH2CH2 O CH2CH3
propane ethoxy ethyl
C O
Aldehyde: one hydrogen atom is bonded to the carbon in the carbonyl group. Ketone: the carbon atom in the carbonyl group is bonded to two hydrocarbon groups.
O R C R' O R H aldehyde C
ketone
R, R' = substituents
Naming Aldehydes
The IUPAC names of aldehydes are obtained by dropping the e and adding -al to the name of the parent hydrocarbon.
butane
butanal al
The parent hydrocarbon is the longest chain that carries the CHO group.
This chain has 4 carbon atoms.
1 4
The parent hydrocarbon is the longest chain that carries the CHO group.
This chain has 5 carbon atoms.
2 1
The CHO group is always at the beginning of the carbon chain. The carbonyl carbon is numbered as carbon 1.
1
3-methylpentanal
The common names of aldehydes are derived from the common names of the carboxylic acids.
The ic acid or oic acid ending of the acid name is dropped and is replaced with the suffix aldehyde.
butyric acid
butyraldehyde
Naming Ketones
The IUPAC name of a ketone is derived from the name of the alkane corresponding to the longest carbon chain that contains the ketone-carbonyl group. The parent name is formed by changing the e ending of the alkane to -one.
propane
propanone one
If the carbon chain is longer than 4 carbons, its numbered so that the carbonyl carbon has the smallest number possible, and this number is prefixed to the name of the ketone.
This end of the chain is closest to the C=O. Begin numbering here.
3-hexanone
The common names of ketones are derived by naming the alkyl or aryl groups attached to the carbonyl carbon followed by the word ketone.
ethyl
propyl
ALKYL HALIDES
General formula: CnH2n+1X where n = 1,2, and X (halogen) Functional group: halogen, -X (X = F, Cl, Br, I)
CH3
2 1
CH3 I iodomethane
4-bromo-2,4-dimethylhexane
AMINES
Amines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair Functional group:
Classification of amines:
Primary amine Secondary amine Tertiary amine
Primary (1o) amine: one hydrogen of ammonia is replaced by an alkyl or aryl group Secondary (2o) amine: two hydrogens of ammonia is replaced by an alkyl or aryl group Tertiary (3o) amine: three hydrogens of ammonia is replaced by an alkyl or aryl group Quaternary (4o) amine: an ion in which nitrogen is bonded to four alkyl or aryl groups and bears a positive charge
NAMING AMINES
Common names: - formed from the names of the alkyl groups bonded to nitrogen, followed by the suffix amine. - the prefixes di-, tri-, and tetra- are used to decribe two, three or four identical substituents.
CH3 CH2
CH3 N CH3
ethyldimethylamine
CH3 N CH3
cyclohexyldimethylamine
NAMING AMINES
IUPAC names: - similar to that alcohols. - the longest continuous chain of carbon atoms determine the root name. - the e in alkane name is changed to amine, and a number shows the position of the amino group along the chain. - other substituents on the carbon chain are given numbers, and the prefix N- is used for each substituent on nitrogen.
NH2 CH CH3
2 1
CH3
4 3 2
NH2
1
CH3 CH2
4 3
2-butanamine
N-methyl-2-butanamine
CARBOXYLIC ACIDS
O C OH
or
Open-chain carboxylic acids form a homologous series. The carbonyl group ( ) is always at the beginning of a carbon chain.
The carbonyl carbon atom is always designated as C-1.
The IUPAC name of a carboxylic acid is derived from the name of the alkane corresponding to the longest carbon chain that contains the carboxyl group.
The parent name is formed by changing the e ending of the alkane to oic acid.
methane
O CH C OH
2 1
CH3 CH
Organic acids are usually known by common names. These names usually refer to a natural source of the acid.
General formula
Example
O R C X O
R C OR' O
R C NH2
O O
O H3C C CI
ethanoyl chloride
Ester Amide
O H3C C OC2H5
ethyl ethanoate
H3C C NH2
ethanamide
Acid anhydride
R C O C R'
H3C C O C CH3
ethanoic anhydride
Esters
IUPAC NAME
According to the IUPAC system the alcohol part of the ester (R) is named first.
ethyl
IUPAC NAME
This is followed by the name of the acid where the ic ending of the acid has been changed to ate.
ethanoate
IUPAC NAME
According to the IUPAC system the alcohol part of the ester (R) is named first. This is followed by the name of the acid where the ic ending of the acid has been changed to ate.
ethyl ethanoate
COMMON NAME
The alcohol part is named first (derived from the common names of alcohol).
The common names of esters are derived by adding ate to the name of the acid.
ethyl
COMMON NAME
The alcohol part is named first (derived from the common names of alcohol).
The common names of esters are derived by adding ate to the name of the acid.
ethyl acetate
Amide
Amide: a composite of a carboxylic acid and ammonia or an amine. Classification of amide: i) primary amide: RCONH2 (two H atoms bonded to N atom) ii) secondary amide: RCONHR (one H atoms bonded to N atom) iii) tertiary amide: RCONRR (no H atoms bonded to N atom)
NAMING AMIDE
IUPAC name: i) primary amide - first name the corresponding acid. Drop the ic acid or oic acid, and add the suffix amide.
O CH3 C OH NH3
ammonia
O CH3 C NH2
ethanamide
acetamide
NAMING AMIDE
IUPAC name: i) secondary and tertiary amide - treat the alkyl groups on nitrogen as substituents, and specify their position by the prefix N-.
O CH3 C N CH2CH3 H
IUPAC Name Common name N-ethylethanamide N-ethylacetamide
O CH3
CH3 C N CH2CH3
N-ethyl-N-methylethanamide N-ethyl-N-methylacetamide
Naming acid halides: - replacing the ic acid suffix of the acid name with yl and the halide name.
O CH3 C F
IUPAC Name Common name ethanoyl fluoride acetyl flouride
O CH3CH2 C CI
propanoyl chloride propionyl chloride
Acid anhydride
Naming acid anhydride: - the word acid is changed to anhydride in both the common and the IUPAC name
O O
CH3 C O C CH3
IUPAC Name Common name ethanoic anhydride acetic anhydride
CH3 C O C H
ethanoic methanoic anhydride acetic formic anhydride
POLYMERS
A polymer is a high molar mass molecular compound made up of many repeating chemical units.
Naturally occurring polymers Proteins Nucleic acids Cellulose Rubber Synthetic polymers
Nylon
Dacron Lucite
Homopolymer is a polymer made up of only one type of monomer ( CF2 CF2 )n ( CH2 CH2 )n ( CH2 CH )n Cl PVC
Teflon
Polyethylene
( CH
CH2
CH2
CH
CH
CH2 )n
Styrene-butadiene rubber
Formation of Polyethylene
General reactions:
Dicarboxylic acids
Diamines
Nylon
Apparel: Blouses, dresses, foundation garments, hosiery, lingerie, raincoats, ski apparel, windbreakers, swimwear, and cycle wear Home Furnishings: Bedspreads, carpets, curtains, upholstery
Industrial and Other Uses: Tire cord, hoses, conveyer and seat belts, parachutes, racket strings, ropes and nets, sleeping bags, tarpaulins, tents, thread, monofilament fishing line, dental floss
AZO-DYES
Azo compounds: - compounds bearing the functional group R-N=N-R', in which R and R' can be either aryl or alkyl. - N=N group is called an azo group - HNNH is called diimide
Aryl azo compounds have vivid colors, especially reds, oranges, and yellows
Methyl orange - used as acid-base indicators due to the different colors of their acid and salt forms Artists paints clays, yellow to red range Dye in food and textiles
E102: Tartrazine
E107 : Yellow 2G
EXAMPLES OF AZO DYES USED IN FOOD
E122 : Azorubine
E123 : Amaranth
E124 : Ponceau 4R
FUEL
Any material that is burned or altered to obtain energy and to heat or to move an object Its energy can be stored to be released only when needed, and that the release is controlled in such a way that the energy can be harnessed to produce work Examples: Methane, petrol and oil. Application of energy released from fuels: - cooking - powering weapons to combustion - generation of electricity Fuel oil: generate heat or used in an engine for the generation of power