Organic Chemistry The study of carbon compounds. Over 10 million compounds naturally exist More than...
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![Page 1: Organic Chemistry The study of carbon compounds. Over 10 million compounds naturally exist More than 300 000 are synthesized.](https://reader030.fdocuments.net/reader030/viewer/2022033100/56649f585503460f94c7cdd5/html5/thumbnails/1.jpg)
Organic ChemistryThe study of carbon compounds.
Over 10 million compounds naturally existMore than 300 000 are synthesized
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Inorganic vs Organic
– oxides of carbon (CO2, CO)
– carbonates,bicarbonates (NaHCO3,CaCO3)
– cyanides (NaCN, etc)
– any carbon attached to a metal and no H
• Hydrocarbons containing CxHy
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Origin of organic compoundsOrigin of organic compounds• Originally from “organic” meaning life• Not just chemistry of life, chemistry of carbon
• Naturally occurring organic compounds are found in plants, animals, and fossil fuels
• All of these rely on the “fixing” of C from CO2
• Synthetic organic compounds are derived from fossil fuels or plant material
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The diversity of carbon compounds is based on the fact carbon atoms Form 4 Bonds
• Forms strong covalent and nonpolar bonds with itself and other elements
Review:• Lewis Structure, Structural formula, Line diagrams
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Carbon molecules form complex 3-D shapes
Common Molecular Shapes
• Tetrahedral
• Trigonal planar
• Linear
• Angular
• Trigonal pyramidal
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Simplest HydrocarbonsSimplest HydrocarbonsC C C C
C C
C
C
C
C
C
C
H
H
H
H
H
H
C C C C C
H
H
H
H
H H
H
H
H
H
H
H
Alkanes Alkenes
Alkynes Aromatics
C C C C C
H
H
H
H
H
H
H
H
H
H
C C C C CH
H
H
H
H
H
H
H
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Naming Hydrocarbons (nomenclature)
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Naming: common vs. IUPAC• Common names used in the 1800’s are still used for some
compounds today: eg.
H C C HCommonly known
as Acetylene
• The International Union of Pure and Applied Chemistry (IUPAC) was established in 1900s
• Systematic method allows an infinite number of compounds to be named given a few rules
IUPAC: Ethyne
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Mnemonic for first four prefixes
First four prefixes• Meth-
• Eth-
• Prop-
• But-
Monkeys
Eat
Peeled
Bananas
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?Decade
Decimal
Decathalon
Other prefixes
• Pent-
• Oct-
• Dec-
• Hex-, Hept-, Non-
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Alkanes
• Are straight or branched-chain containing only single bonds
• Are a homologous series –a group of compounds whose members differ by the addition of the same structural group
• Named by using prefix and ending -ane
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TASK
• Write chemical and structural formula for all alkanes that contain up to 10 carbons
• Methane CH4 • Ethane CH3CH3
• Propane CH3CH2CH3
• Butane CH3CH2CH2CH3
• Pentane• Hexane• Heptane• Octane• Nonane• Decane• This is just the beginning……………………………………………………………..
You may have noticed that branching creates enormous variation
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Try Naming TheseTry Naming These
CH3
CH2CH2
CH2CH2
CH2CH2
CH2CH2
CH3
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Structural Isomers
• Substances with the same chemical formula by different arrangements of atoms
• Eg. Butane & 2 methyl-propane
***Isomers have different physical and chemical properties
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TASK: Draw all the isomers for pentane and hexane
Did you know?• 3 isomers of pentane• 5 isomers of hexane• Heptane-9 • Octane-18 • Nonane-35 • Decane-75 • making a total of 150 different possible alkane
compounds containing 10 carbons.
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C
C
C
CC H
HHH
H
H
HH H
H
Greater complexity exists because organic compounds can form Cyclic (ring) structures?
• Cyclic structures are circular• Have “cyclo” in name
• Eg. Cyclopropane Cyclopentane
CH2
CH2
CH2
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TASK
• Study the following graphic.
• What 2 trends can be identified?
• Hypothesize why these trends exist.
• TASK 2: Compare, contrast and explain the physical properties of the first 10 alkanes
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Background: formulas for HxCy
• CH single bonds Alkanes= CnH2n+2,
• CH with one double bond Alkenes= CnH2n,
• CH with two double bonds Alkynes= CnH2n-2
• Q - How many hydrogens in each of these:Alkane C6H
Alkene C22HCH3 CH3
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Basic names of hydrocarbons• Hydrocarbon names are based on:
– 1) class – 2) # of C, – 3) side chain type – 4) position
Q - What names would be given to these:7C, 9C alkane2C, 4C alkyne1C, 3C alkene
heptane, nonaneethyne, butynedoes not exist, propene
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Numbering carbonsQ- draw penteneA- Where’s the bond?
We number C atoms
• Always start numbering for the carbon nearest the double bond the lowest number
• Q - Name these
C C C CCH3
H
H
H
H H H
HCH31
C2
C3
C4
C5
H
H
H
H H H
HCH35
C4
C3
C2
C1
H
H
H
H H H
H
Ethene
3-nonyne
2-buteneCH3
CH
CH
CH3
CH3 CH3
C2H4
1-pentene
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Multiple multiple bonds
• Rules• Give 1st bond lowest #• include di, tri, tetra, penta, etc. before ene/yne• Comma between #s, hyphen between #-letter
2,3-heptadieneCH3CH3
CH3
CH2CCCCCCCH32,4,6-nonatriyne
C C C C
H
H
H
H
H
H
CH3CH2CH2CH=C=CH2
CH2CCH
CHCH2
2-butyne
1,2-hexadiene1,2,4-pentatriene
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Cyclic structuresQ- Draw these:
cyclobutene 1,3-cyclopentadiene cyclopropane
CH2
CH
CH2
CHCC
C CCH
H H
H
H H
CH2
CH2
CH2
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CH3 CH3
CH3
CH3Naming side chains
• Names are made up of: side chains, root
• Root is the longest possible HC chain• Must contain multiple bonds if present• Add -yl to get name of side chain
• Common side chains include:CH3- methyl CH3CH2- ethyl
CH3CH2CH2- propyl (CH3)2CH- isopropyl
• 2,3-dimethylpentane
CH3 CH3
CH3
CH3
CH3CH
CH3
*
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ene
Naming side chainsExample: use the rules on the bottom of
handout to name the following structure
CH3 CH2 C
CH2
CH2 C
CH2
CH3
CH3
CH3
Rule 1: choose the correct ending
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ene
Rule 2: longest carbon chain
Naming side chains
CH3 CH2 C
CH2
CH2 C
CH2
CH3
CH3
CH3
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1-hexene ene
Rule 3: attach prefix (according to # of C)
Naming side chains
CH3 CH2 C
CH2
CH2 C
CH2
CH3
CH3
CH3
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Rule 4: Assign numbers to each carbon
1-hexene
Naming side chains
CH3 CH2 C
CH2
CH2 C
CH2
CH3
CH3
CH3
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Rule 4: Assign numbers to each carbon
CH3 CH2 C2
CH21
CH23
C4
CH25
CH3
CH3
CH36
CH3 CH2 C
CH2
CH2 C
CH2
CH3
CH3
CH3
1-hexene 1-hexene
Naming side chains
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CH3 CH2 C2
CH21
CH23
C4
CH25
CH3
CH3
CH36
Rule 5: Determine name for side chains
CH3 CH2 C
CH2
CH2 C
CH2
CH3
CH3
CH3
1-hexene 1-hexene
Naming side chains
ethyl
methyl
methyl
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CH3 CH2 C
CH2
CH2 C
CH2
CH3
CH3
CH3
CH3 CH2 C2
CH21
CH23
C4
CH25
CH3
CH3
CH36
1-hexene2-ethyl-4-methyl-4-methyl-1-hexene
Naming side chains
ethyl
methyl
methyl
Rule 6: attach name of branches
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Rule 7: list alphabetically
CH3 CH2 C
CH2
CH2 C
CH2
CH3
CH3
CH3
CH3 CH2 C2
CH21
CH23
C4
CH25
CH3
CH3
CH36
1-hexene2-ethyl-4-methyl-4-methyl-1-hexene
Naming side chains
ethyl
methyl
methyl
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Rule 8,9: group similar branches
CH3 CH2 C
CH2
CH2 C
CH2
CH3
CH3
CH3
CH3 CH2 C2
CH21
CH23
C4
CH25
CH3
CH3
CH36
1-hexene2-ethyl-4-methyl-4-methyl-1-hexene
Naming side chains
ethyl
methyl
methyl
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Rule 8,9: group similar branches
CH3 CH2 C
CH2
CH2 C
CH2
CH3
CH3
CH3
CH3 CH2 C2
CH21
CH23
C4
CH25
CH3
CH3
CH36
2-ethyl-4,4-dimethyl-1-hexene
Naming side chains
ethyl
methyl
methyl
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Try Naming Side Chains
CH3 CH2
CH CH3
CH2CH2
CH3
CH3 CH
CH
CH3
CH
CH3
CH2 CH2 CH3
CH2 CH3
CH3CH2CH CH CH CH2CH CH3
CH3
CH2CH3
CH3 CH3
3-methylhexane4-ethyl-2,3-dimethylheptane
5-ethyl-2,4,6-trimethyloctane
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Naming side chains
3-ethyl-2-methylpentane
3-ethyl-1,5,5-trimethylcyclohexene
CH3CH
CHCH2
CH3
CH3
CH2CH3
CH3 CH3
CH3CH3
Name the structures below
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Try Drawing These2,2-dimethyloctane
1,3-dimethylcyclopentane
1,1-diethylcyclohexane
6-ethyl-5-isopropyl-7-methyl-1-octene
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Try Naming Try Naming
CH3 CH3
CH3
CH3
CH3
CH3
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Aromatic Hydrocarbons
• Aromatic compounds contain benzene ring structures and their derivatives.
• Benzene (C6H6)• most commonly used organic (nonpolar)
solvent• very stable substance, unreactive • toxic if inhaled -carcinogenic• produced by processing coal, crude oil,
gasoline or the combustion of rubber tires
• if it occurs as a side chain it is called a phenyl group
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Resonance• The properties of this compound can be explained by following theory:
-the chemical bonds between carbon atoms are not single or double-all bonds between carbons in the benzene ring are identical in length and strength -there is an even distribution of valence electrons around the entire molecule.
• The resonance of the single and double bonds accounts for the stability of aromatic compounds.
• This is illustrated by resonance structures:
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There are 2 naming methods1) Numbering carbons2) ortho, meta, para (stomp)
Aromatic nomenclature
CH3
Ortho
Para
ST Meta
CH3
CH3
CH3
CH3
CH3CH3
1,2-dimethylbenzeneorthodimethylbenzene
1,3-dimethylbenzenemetadimethylbenzene
1,4-dimethylbenzeneparadimethylbenzene