Transcript PowerPoint - Name Hydrocarbons

Naming Hydrocarbons
(nomenclature)
Organic Compounds
• __________ Compounds - any covalently
bonded compound containing carbon
(except __________ , __________ and
__________ )
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
Saturated & Unsaturated
Hydrocarbons
• Saturated hydrocarbons – contain only
__________ carbon-carbon bonds
(__________ )
• Unsaturated hydrocarbons – contain
double carbon-carbon bonds
(__________) or triple carbon-carbon
(__________ ) bonds
Formulas
• Alkanes = CnH2n+2
• Alkenes = CnH2n
• Alkynes = CnH2n-2
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
Example
• Name C3H8
Mnemonic for first four prefixes
First four prefixes
•
•
•
•
MethEthPropBut-
Monkeys
Eat
Peeled
Bananas
Numbering carbons
Q- draw pentene
• Q - Name these
H3C
H 3C
C
H
H
C
C 2H 4
CH3
CH3
Multiple multiple bonds
H3C
CH3 2,3-heptadiene
H3C
C
C
C
C
C
C
2,4,6-nonatriyne
•
•
•
•
CH2
CH3
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
H
H 2-butyne
HC C CH2
H
C
C
C
C
H
H2C
CH
1,2,4-pentatriene
CH3CH2CH2CH=C=CH2 1,2-hexadiene
H
H
Cyclic structures
• Cyclic structures are circular
• Have “cyclo” in name
H
H
H
H
C
C
H
H
C
C
C
H
H
H
H
• cyclopentane
Q- Draw these (note: carbons in a double bond
should be consecutive- 1 and 2, 5 and 6, etc.):
cyclobutene 1,3-cyclopentadiene cyclopropane
H
H 2C
CH2
HC
CH
H
H
C
C
C
H
C
C
H
CH2
H
H2C
CH2
Naming side chains
CH3
CH33
H3C
• Names are made up
of: side chains, root
• 2,3-dimethylpentane
CH3
• Root is the longest possible HC chain
• Must contain multiple bonds if present
• Add -yl to get name of side chain H C
CH3
3
• Common side chains include:
CH
CH3- methyl
CH3CH2- ethyl
*
CH3CH2CH2- propyl (CH3)2CH• isopropyl
Br- (bromo), Cl- (chloro), F- (fluoro), I- (iodo)
Naming side chains
Example: name the following structure
CH2
CH3 CH2 C
CH2 CH3
CH2 C
CH3
CH3
Rule 1: choose the correct ending
ene
Naming side chains
CH2
CH3 CH2 C
CH2 CH3
CH2 C
CH3
CH3
Rule 2: longest carbon chain
ene
Naming side chains
CH2
CH3 CH2 C
CH2 CH3
CH2 C
CH3
CH3
Rule 3: attach prefix (according to # of C)
1-hexene
ene
Naming side chains
CH2
CH3 CH2 C
CH2 CH3
CH2 C
CH3
CH3
Rule 4: Assign numbers to each carbon
1-hexene
Naming side chains
CH2
CH2 CH3
1
CH3 CH2 C
2
5
CH2 C
3
4
6
CH3
CH3
Rule 4: Assign numbers to each carbon
1-hexene
Naming side chains
CH2
ethyl
CH2 CH3
1
CH3 CH2 C
2
5
CH2 C
3
4
CH3
6
CH3
methyl
methyl
Rule 5: Determine name for side chains
1-hexene
Naming side chains
CH2
ethyl
CH2 CH3
1
CH3 CH2 C
2
5
CH2 C
3
4
CH3
6
CH3
methyl
methyl
Rule 6: attach name of branches
2-ethyl-4-methyl-4-methyl-1-hexene
1-hexene
Naming side chains
CH2
ethyl
CH2 CH3
1
CH3 CH2 C
2
5
CH2 C
3
4
CH3
6
CH3
methyl
methyl
Rule 7: list alphabetically
2-ethyl-4-methyl-4-methyl-1-hexene
1-hexene
Naming side chains
CH2
ethyl
CH2 CH3
1
CH3 CH2 C
2
5
CH2 C
3
4
CH3
6
CH3
methyl
methyl
Rule 8,9: group similar branches
2-ethyl-4-methyl-4-methyl-1-hexene
1-hexene
Naming side chains
CH2
ethyl
CH2 CH3
1
CH3 CH2 C
2
5
CH2 C
3
4
CH3
6
CH3
methyl
methyl
Rule 8,9: group similar branches
2-ethyl-4,4-dimethyl-1-hexene
Naming side chains
H3C
H3C
CH2
CH CH3
H2C
CH2
CH CH CH2 CH3
H3C
CH3
3-methylhexane
CH2 CH2 CH3
CH
CH3
4-ethyl-2,3-dimethylheptane
CH3
CH3
CH3
CH3 CH2 CH CH CH CH2 CH CH3
CH2 CH3
5-ethyl-2,4,6-trimethyloctane
Naming side chains
Name the structures below
CH3
CH
H3C
CH2
CH
CH3
H2C
H3C
H3C
3-ethyl-2-methylpentane
CH3
CH3
3-ethyl-1,5,5trimethylcyclohexene
CH3
More practice
Br
4-bromo-7-methyl-2-nonene
Br
2,5-dibromo-6-chloro-1,3-cycloheptadiene
Br
Cl
CH3
H3C
C
CH3
CH2 C
F
CH CH CH CH3
5-fluoro-7,7-dimethyl-2,4-octadiene
Functional Groups
Class
Alcohol
Functional group
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’’
1
CH2
CH3
CH2
CH2
CH2
CH2
CH3
CH2
2 CH3
4
CH
CH3
CH2
CH2
CH2
CH
CH3
CH3
CH2
H2C
CH3
3
octane
2,5-dimethyloctane
CH3
CH3 CH2 CH CH C
CH
H2C
CH3
2,2-dimethyl-3-hexene CH3
CH2
CH2 CH
CH2 CH3
1,3-diethylcyclopentane
5
CH2
CH3
CH
CH2
CH2
CH
CH2
CH2
CH3
4-nonene
6
CH2
H2C
8
CH2
cyclopropane
7
H3C
H3C
3,3-dimethylcyclopentene
6-ethyl-2-octyne
9
3-methylhexane
H3C
H3C
H2C
CH2 CH2 CH3
CH CH CH2 CH3
CH2
CH CH3
H3C
CH2
CH
CH3
CH3
11
10
4-ethyl-2,3-dimethylheptane
CH3
CH3
CH3
CH3 CH2 CH CH CH CH2 CH CH3
CH2 CH3
5-ethyl-2,4,6-trimethyloctane
12
13
3,4-diethyl-2-hexene
CH3
CH
CH3
C
CH3
H 2C
CH2
HC
CH
cyclobutene
CH2
15
CH3
CH2 CH
CH2 CH
CH2
CH2 CH3
CH
CH2
14
CH2
CH
H2C
CH3
CH2
CH2 CH2
CH2
benzene
H3C
1,2-dimethyl-6-propylcyclodecane
CH3
16
CH3
H3C
CH3
2,7,8-trimethyldecane
CH3
17
19
CH3 CH CH CH2 CH2 CH3
2-hexene
18 H C
3
H3C
CH3
CH2
CH3 CH2 C CH2 CH3
CH2
CH3
CH3
3,3-diethylpentane
4-ethyl-1,2-dimethylcycloheptane
20
CH3
CH
H3C
CH2
CH
CH3
H2C
CH3
3-ethyl-2-methylpentane
21
H3C
H3C
CH3
CH3
3-ethyl-1,5,5-trimethylcyclohexene