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Organic Chemistry
The chemistry of compounds containing carbon.
Refinery and tank storage facilities, like this one in Texas, are needed to change the hydrocarbons of crude oil to many different petroleum products. The classes and properties of hydrocarbons form one topic of study in organic chemistry.
hydrocarbons
A hydrocarbon is a compound consisting of only hydrogen and carbon.
The carbon to carbon can be single, double, or triple bonds.
The bonds are always nonpolar.
HYDROCARBONS
Here are some Characteristics of hydrocarbons:
Has non-polar molecules
sp3 hybridization
Contains only hydrogen and carbon
non-electrolytes because of poor ionization
In "most** situations, it is not soluble in water
The reactivity is very slow
The low boiling point makes it pretty easy to decompose
an organic compound (as acetylene or butane) containing only carbon and hydrogen and often occurring in petroleum, natural gas, coal, and bitumens
Presented by Brent Daigle, Ph.D. (ABD)
Carbon-to-carbon bonds can be single (A), double (B), or triple (C). Note that in each example, each carbon atom has four dashes, which represent four bonding pairs of electrons, satisfying the octet rule.
Carbon-to-carbon chains can be (A) straight, (B) branched, or (C) in a closed ring. (Some carbon bonds are drawn longer, but are actually the same length.)
Straight vs branched
Classification of Organic Molecules
Functional Groups
3-8
1. Hydrocarbons - molecules that possess only hydrogen and carbon
a1. Alkanes – noncyclic hydrocarbons with only C-C single bonds. Formula CnH2n+2 where n is an integer.
a2. Cycloalkanes – cyclic hydrocarbons with only C-C single bonds. Formula CnH2n where n is an integer.
Example: Butane CH3CH2CH2CH3 C4H10
Example: Cyclobutane C4H8
b1. Alkenes – noncyclic hydrocarbons with C=C double bonds. Formula CnH2n where n is an integer.
Example: 2-Butene CH3CH=CHCH3 C4H8
3-9
c. Alkynes – noncyclic hydrocarbons with C≡C triple bonds. Formula CnH2n-2 where n is an integer.
Example: Butyne CH3C ≡ CCH3 C4H6
b2. Cycloalkenes – cyclic hydrocarbons with C=C double bonds. Formula CnH2n-2 where n is an integer.
Example: Cyclobutene C4H6
d. Aromatic Hydrocarbons – benzene and its derivatives
C
CC
C
CC H
H
HH
H
H
or C6H6
3-10
2. Compounds containing Oxygen
a. Alcohols R-OH
Functional Group OH hydroxyl group
CH3OH methyl alcohol HOCH2CH2OH ethylene glycol (antifreeze)
b. Ethers R-O-R
CH3CH2-O-CH2CH3 Diethylether
c. Aldehydes and Ketones
R-C-H
O
R-C-R'
O
Functional Group C=O carbonyl group
OO
O
H
3-11
d. Carboxylic Acids
Functional Group -CO2H -COOH -COH Carboxyl Group
R-C-OH
O
O
CH3-C-OH
O
OH2H3O+ CH3CO-
O
+ +Acetic Acid
e. Derivatives of Carboxylic Acids
R-C-OR'
O
R-C-Cl
O
R-C-NH2
O
Ester Acid Chloride Amide
3-12
3. Nitrogen-Containing Molecules
a. Amines R-NH2
Functional Group -NH2 amino groupCH3NH2
NH
N
Amines are Lewis and Bronsted bases because of the nonbonded pair of electrons
NH2ClH NH3+ Cl+..
b. Amides (see above)
c. Nitriles R C N
Functional Group Cyano Group
C N
3-13
Single versus Double Bonds
C C
H
H
HH
H
H
Ethane
The carbon-carbon single bond in ethane freely rotates at room temperature.
CC
HH
HH
Ethylene
The carbon-carbon double bond in ethylene does not freely rotate at room temperature.
Why not?
CC
HH
HH
C C
HH
H
HH
H
Answer: The Pi bond would have to be broken. It will not break at room temperature
Pi bond broken
3-14
Isomers – different compounds with the same formula
a. Constitutional (Structural) Isomers – isomers that differ in their bonding sequence
CH3CHCH2CH3\
CH3
CH3CH2CH2CH2CH3vs
C5H12 C5H12
C=CCl
H H
Br
C=CH
H Cl
Br
C2H2BrCl C2H2BrCl
b. Stereoisomers – isomers that differ in their spatial orientation
C=CCl
H H
Br
C=CCl
H Br
H
C2H2BrCl C2H2BrCl Cis isomer Trans isomer
3-15
Use of Wedges and Dashed Lines
CH
H
HH
Solid Wedge indicates “coming toward you”Dashed Line indicates “going away”Narrow Line indicates “in the plane of paper”
CH3
CH3
CH3
CH3
Question: Are the above cycloalkanes constitutional or stereoisomers?
Answer: Stereoisomers
ALKANE Alkanes are hydrocarbons with only single bonds.• SATURATED HYDROCARBONS – they contain only C
& H• they have only C-C and C-H single bonds• Contain the maximum possible number of H per C• Occasionally referred to as ALIPHATIC compounds;
Greek aleiphas, meaning fat (many animal fat contain long carbon chains similar to alkanes)
Alkanes occur in what is called a homologous series.
Each successive compound differs from the one before it only by a CH2
The AlkanesCharacteristics
AKA Paraffins, are chemical compounds that consist only of the elements carbon (C) and hydrogen (H). Each are linked by a single bond.
Each carbon atom must have 4 bonds (either C-H or C-C bonds), and each hydrogen atom must be joined to a carbon atom (H-C bonds).
General formula CnH2n+2 (Linear saturated hydrocarbon)
Brent Daigle, Ph.D. (ABD)
Methane
PHYSICAL PROPERTIES1. Non-polar –
comparable EN of C & H; symmetrical cmpd.
2. Low b.p. (-161.5o), or low m.p.(-83o) – weak VW attraction.
3. Colorless4. Sp. Gravity = 0.4 g/mL5. Slightly soluble in water
the simplest alkane
Chemical structure of methane
Tetrahedral109.5o
MW=16 g/ml
SOURCES:1. END PRODUCT OF ANAEROBIC
DECAY OF PLANT AND ANIMALS It is a major constituent of natural
gas (97%) Fire damp of coal mines Marsh gas bubbling in swamp Methane can be isolated by
fractional distillation
2. OXIDATION BY HALOGENS (HALOGENATION)
The Alkanes
Methane H
H C H CH4
H
Propane H H H
H C C C H C3H8
H H H
Ethane H H
H C C H C2H6
H H
Presented by Brent Daigle, Ph.D. (ABD)
Vocabulary Review (Time to pull out the ‘ole Latin Textbook)
The number of carbon atoms = root name! meth 1 carbon eth 2 carbon prop 3 carbon but 4 carbon pent 5 carbon hex 6 carbon hept 7 carbon oct 8 carbon non 9 carbon dec 10 carbon
Presented by Brent Daigle, Ph.D. (ABD)
3-21
Physical Properties of Alkanes1. Combustion - Alkanes are flammable, i.e. they burn.
CH4 O2 CO2 OH2+ +2 2
2. Boiling and melting points a. Both bp and mp increase with increasing carbon number for straight-chain alkanes with formula CnH2n+2
Carbon Number Physical State C1- C4 gases C5 – C16 liquids C17 – C30 oils and greases C30 – C50 paraffin waxes >C50 plastics (polyethylene)
3-22
b. Branching tends to lower the boiling point and raise the melting point
BP 60oC 58oC 50oC
MP -154oC -135oC -98oC
Explanation: MP Branching reduces the flexibility of the molecule which
reduces the entropy term S in the equation Tmp = H/S. Since S is in the denominator,
Tmp increases.
BP Branching reduces surface area (more compact structure), and therefore London dispersion forces which control boiling point for these molecules.
3. Solubility – alkanes are nonpolar molecules and therefore insoluble in water,which is polar. Alkanes are hydrophobic.
4. Densities – alkanes are less dense than water, with densities near 0.7 g/mL. Therefore they float on water, e.g. Exxon Valdez oil spill.
Petroleum is a mixture of alkanes, cycloalkanes, and aromatic hydrocarbons. Petroleum is formed from the slow
decomposition of buried marine life, primarily plankton and algae.
As petroleum is formed it is forced through porous rock until it reaches an impervious layer of rock. Here it forms an accumulation of petroleum
and saturated the porous rock creating an oil field.
Crude oil is the petroleum that is pumped directly from the ground. It is a complex mixture of
hydrocarbons with one or two carbon atoms up to a limit of about 50 carbon atoms.
This is usually not useful, so it must separated by distillation.
Crude oil from the ground is separated into usable groups of hydrocarbons at this Louisiana refinery. Each petroleum product has a boiling point range, or "cut," of distilled vapors that collect in condensing towers.
Petroleum products and the ranges of hydrocarbons in each product.
The octane rating scale is a description of how rapidly gasoline burns. It is based on (A) n-heptane, with an assigned octane number of 0, and (B) 2,2,4-trimethylpentane, with an assigned number of 100.
3-28
Octane Number
Straight-chain hydrocarbons have low octane and make poor fuels.
Octane Number = 0
Branched Alkanes burn more slowly and reduce the knocking in the engine.
heptane
2,2,4-trimethylpentane
Octane Number = 100
3-29
1. The first step in petroleum refining is fractional distillation.
Distilling Crude Oil
Separate fractions
based on differences in boiling point.
3-31
Refining of Petroleum
3-32
2. Upstream processing of the distillates.
a. Catalytic hydrocracking – produces small alkanes from large alkanes by adding hydrogen.
H2, heat
Si-Al catalyst
b. Catalytic cracking – produces small alkenes and alkanes by cracking in the absence of hydrogen.
heat
Si-Al catalyst
c. Catalytic Reforming – the alkanes and cycloalkanes are upgraded to higher octane number by conversion into aromatic compounds.
-3H2-H2
catalyst, heat catalyst, heat
Alkyl Groups Removing HYDROGEN from
an alkane, the partial structure that remains is called an ALKYL GROUP.
Are NOT stable compounds themselves, they are simply PARTS of larger compounds.
Are named by replacing the –ane ending of the parent alkane with a –yl ending.
In naming alkyl groups: the prefixes sec- (for secondary) and tert- (for tertiary) used for the C4 alkyl groups, refers to the number of other carbon atoms attached to the branching carbon atom.
There are 4 possibilities: primary (1o), secondary (2o), tertiary (3o) and quaternary (4o).
Sample problems
answers
NOMENCLATURE