Download - Naming Hydrocarbons (nomenclature)
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Naming Hydrocarbons (nomenclature)
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Organic Compounds
• __________ Compounds - any covalently bonded compound containing carbon (except __________ , __________ and __________ )
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Hydrocarbons
• __________ - Organic compounds that contain only carbon & hydrogen
• __________ - contain only single covalent bonds
• __________ - contain one or more carbon - carbon double bond
• __________ - contain one or more carbon-carbon triple bond
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Saturated & Unsaturated Hydrocarbons
• Saturated hydrocarbons – contain only __________ carbon-carbon bonds (__________ )
• Unsaturated hydrocarbons – contain double carbon-carbon bonds (__________) or triple carbon-carbon (__________ ) bonds
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Formulas
• Alkanes = CnH2n+2
• Alkenes = CnH2n
• Alkynes = CnH2n-2
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Nomenclature
• Must memorize prefixes• To name, look at the
formula for the hydrocarbon
• Determine if it is an alkane, alkene, or alkyne
• Use the prefix for the number of carbons
• Add ending (ane, ene, yne)
Prefix # of carbon atoms
Meth- 1
Eth- 2
Prop- 3
But- 4
Pent- 5
Hex- 6
Hept- 7
Oct- 8
Non- 9
Dec- 10
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Example
• Name C3H8
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Mnemonic for first four prefixes
First four prefixes• Meth-
• Eth-
• Prop-
• But-
Monkeys
Eat
Peeled
Bananas
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Numbering carbonsQ- draw pentene
• Q - Name these
CH3CH
CH
CH3
CH3 CH3
C2H4
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Multiple multiple bonds
• Give 1st bond (1st point of difference) lowest #• include di, tri, tetra, penta, etc. before ene/yne• Comma between #s, hyphen between #-letter• You do not need to know ene + yne
2,3-heptadieneCH3CH3
CH3
CH2CCCCCCCH3
2,4,6-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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C
C
C
CC H
HHH
H
H
HH H
H
Cyclic structures• Cyclic structures are circular• Have “cyclo” in name
• cyclopentaneQ- Draw these (note: carbons in a double bond
should be consecutive- 1 and 2, 5 and 6, etc.): 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
*
• Br- (bromo), Cl- (chloro), F- (fluoro), I- (iodo)
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ene
Naming side chainsExample: 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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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
CH3
CHCH
CH2CH3
CH3
CH2CH3
CH3 CH3
CH3CH3
Name the structures below
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More practice
4-bromo-7-methyl-2-nonene
5-fluoro-7,7-dimethyl-2,4-octadiene
BrBr Br
Cl
CH3 C CH2C CH CH CH CH3
CH3
CH3
F
2,5-dibromo-6-chloro-1,3-cycloheptadiene
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Functional Groups
Class Functional group
Alcohol R – OH
Ether R — O — R’
Aldehyde O || R — C — H
Ketone O || R — C — R’
Carboxylic acid O || — C — OH
Ester O || R — C — O — R’
Amine R ’ | R — N — R’’
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2,2-dimethyl-3-hexene
2,5-dimethyloctane
octane
1,3-diethylcyclopentane
CH3
CH2CH2
CH2CH2
CH2CH2
CH3
CH3
CHCH2
CH2CH
CH2CH2
CH3
CH3
CH3
CH2
CH
CH2
CHCH2
CH2
CH3
CH2CH3
CH2 CH CH C CH3CH3
CH3
CH3
1
2
3
4
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CH2
CH2
CH2
CH3
CH3
CH3
CH2CH2
CH
CH
CH2CH2
CH2CH3
3,3-dimethylcyclopentene
cyclopropane
4-nonene
6-ethyl-2-octyne
5
6
7
8
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CH3 CH2
CH CH3
CH2CH2
CH3
CH3 CH
CH
CH3
CH
CH3
CH2 CH2 CH3
CH2 CH3
5-ethyl-2,4,6-trimethyloctane
CH3CH2CH CH CH CH2CH CH3
CH3
CH2CH3
CH3 CH3
3-methylhexane
4-ethyl-2,3-dimethylheptane
9 10
11
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cyclobutene
CH
CH2
CH
CH2
CHCH2
CH2
CH3
CH3
CH2
CH2
CH2 CH2
CH2
CH3
CH2 CH
C CH2
CH2 CH3
CH
CH3
CH3
CH3
1,2-dimethyl-6-propylcyclodecane
CH2
CH
CH2
CH
benzene
3,4-diethyl-2-hexene12 13
14
15
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4-ethyl-1,2-dimethylcycloheptane
2-hexene
2,7,8-trimethyldecane
3,3-diethylpentane
CH2 C CH2
CH2
CH2
CH3
CH3 CH3
CH3
CH3CH3
CH3 CH3
CH3
CH3 CH3
CH3
CH3 CH CH CH2 CH2 CH3
16
17
18
19
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3-ethyl-2-methylpentane
CH3 CH3
CH3CH3
3-ethyl-1,5,5-trimethylcyclohexene
CH3
CHCH
CH2CH3
CH3
CH2CH3
20
21