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Organic
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Kinds of Hydrocarbons
• Aliphatic– Chains or rings of carbon atoms– May be planar or non - planar
• Aromatic– Planar molecules– Usually contain one or more benzene rings
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Aliphatic Hydrocarbons
• Hydrocarbons - contain only C and H
• Names of carbon chains # of C atoms Root Name
1 meth - 2 eth - 3 prop - 4 but - 5 pent - 6 hex - 7 hept - 8 oct - 9 non - 10 dec -
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Alkanes
• Saturated hydrocarbons• Contain no double or triple bonds• Naming
– Root name + ane
• General Formula: CnH2n+2
H H H
H C C C H
H H H
CH3CH2CH3
propane
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Alkenes
• Unsaturated hydrocarbons• Contain one double bond• Naming
– Root name + ene
H H H
H C C C H
H
CH3CHCH2
propene
• General Formula: CnH2n
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Alkynes• Unsaturated hydrocarbons• Contain one triple bond• Naming
– Root name + yne
• General Formula: CnH2n-2
H
H C C C H
H
CH3CCH
propyne
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Cycloalkanes
• Unsaturated hydrocarbons
• Contain one ring
• Naming– Cyclo + root name+ ane
H H
H H
H H H H
H H
H H
cyclohexane
C6H12
General formula: CnH2n
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Alkdienes
• Unsaturated hydrocarbons
• Contain 2 double bonds
• Naming: root name + diene
H H H
C C C C
H H H
CH2CHCHCH2
butadiene
General Formula: CnH2n-2
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Positional Isomers
Positional Isomers occur when the hydrocarbon can have a multiple bond (or functional group) in a different location.
Butene(C4H8)
4 carbon chain
1 double bond
H H H
C C C C H
H H H H
H H
H C C C C H
H H H H
1-butene
2-butene
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Functional Groups
Oxygen Containing
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Alcohol R - O - H
Naming Root name + bonding + ol
CH3CH2CH2OH propanol
CH2CHCH2OH propenol
Ether R - O - R
Naming R and R :Root name with yl ending + ether
CH3CH2OCH3 Ethyl methyl ether
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Aldehyde R - CHO
Naming Root name + bonding + al
CH3CH2CHO propanal
CH2CHCHO propenal
Ketone
O
R - C - R
Naming Root Name + bonding + one
CH3CH2COCH3 butanone
CH2CHCOCH3 butenone
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Carboxylic Acid O
R - C - O H
Acidic H
Naming Root name + bonding + oic acid
CH3CH2CH2COOH Butanoic acid
Lose acidic H, yields anion
CH3CH2CH2COO - Butanoate ion
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Ester O
R - C - O R’
Naming R ’ alkyl + root name + bonding + oate
O
CHe CH2 CH2 C O CH2 CH3
ethyl butanoate
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Anhydride O O
R C O C R
Two acids joined together with the loss of water
Naming
We will limit to both acids the same
Acid name + anhydride
O O
CH3CH2CH2 C O C CH2CH2CH3
Butanoic anhydride
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Nitrogen containing functional groups
Amines
Primary amine (1o) R - NH2
Secondary amine (2o) R,R ‘NH
2 H on N
1 H on N
Tertiary amine (3o) R,R ‘R”N 0 H on N
Naming R, R’ , R” named as alkyls + amine
CH3NH2 methylamine
(CH3)(CH3CH2)NH ethylmethylamine
(CH3)3N trimethylamine
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Amide RCONH2
OR- C-NH2
Naming Root + bonding + amide
O
CH3CH2C - NH2
propanamide
Can substitute on the N, name as alkyl prefix
O
CH3CH2C - NHCH3
Methylpropanamide
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Common Substituents
- Cl chloro
- Br bromo- I iodo
- NO2 nitro- NH2 amino
- OH hydroxy
- R alkyl (hydrocarbon added to primary chain)
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Common names of some organic substituents
CH3
CH
CH3
isopropyli - propyl
CH3
CH CH2
CH3
isobutyli - butyl
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CH3
H3C C
CH3
tertiary butylt - butyl
CH2 CH vinyl
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Naming substituted hydrocarbons
1. Name the longest chain
2. Add the compound type (suffix)
3. Add prefix to indicate any substituents or branches
4. Indicate the position with a number for the carbon it is attached to.
O
CH3 CH CH2 CH2 CH
CH2 CH3
hexanal4-methyl
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What is the BEST name for :
O
CH3 CH CH2 C CH3
ClA)ChloropentanoneB)2-chloro-4-pentanoneC)4-chloro-2-pentanoneD)2-chloropentanalE)4-chloro-1-methylbutanone
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What is the BEST name for :
O
CH3 CH CH2 C CH3
ClA)ChloropentanoneB)2-chloro-4-pentanoneC)4-chloro-2-pentanoneD)2-chloropentanalE)4-chloro-1-methylbutanone
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What is the BEST name for:
(CH3CH2)2NH
A)Ethyl amideB)DimethylamineC)1,1-ethylamineD)DiethylamineE)diethylamide
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Common Names
carbontetrachloride CCl4chlorform CHCl3Methylene chloride CH2Cl2methylchloride CH3Cl
freon CCl2F2
acetone O
CH3 - C - CH3
acetic acidO
CH3 - C - O - H
O
CH3 - C - O
Acetate ion
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acetaldehyde O
CH3 - C - H
formaldehyde O
H - C - H
Formic acid O
H - C - O - H
(di)ethylether CH3CH2OCH2CH3
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CH3CH2OH Ethyl alcohol
CH3OH Methyl alcohol
Oxalic acidO O
H - O -C - C - O - H
GlycerineO - H O - H O - H
CH2 - CH - CH2
glycerol
1,2,3 - propanetriol
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NO2 NO2 NO2
O O O
CH2 - CH - CH2
nitroglycerine
urea O
H2N C NH2
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Aromatic Compounds
All contain benzene rings (C6H6) H H
H H
H H
H H
H H
H HResonanceforms
Electrons shift so quickly that they are called delocalized electrons.
Add extra stability
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Benzene is represented by
Naming monosubstituents
CH2CH3
ethylbenzene
R
alkylbenzene
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Cl
chlorobenzene
NH2
aminobenzeneaniline
NO2
nitrobenzene
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More than 1 substituent need to identify where
1
2 3
4
56
2 the sameBr Br
1,2 - dibromobenzene
ortho - dibromobenzene
o - dibromobenzene
Br
Br
1,3 - dibromobenzene
meta - dibromobenzene
m - dibromobenzene
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Br
Br
1,4 - dibromobenzene
para - dibromobenzene
p - dibromobenzene
Br
NO2
1,3 - bromonitrobenzene
meta - bromonitrobenzene
m - bromonitrobenzene
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If benzene is used as an attachmentIt is called phenyl
CH3
CHCH3
2 - phenylpropane
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Fused benzene rings - share 2 C’s
Polycyclic compounds
naphthalene anthracene
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/115 letter56.35 D60.95 D+65.55 C-71.3 C77.05 C+82.8 B-88.55 B94.3 B+
100.05 A-105.8 A
Average = 85.7Median = 89
Exam 1
Frequency
0
5
10
15
20
25
30
35
0 6
12
18
24
30
36
42
48
54
60
66
72
78
84
90
96
102
108
114
120
126
Frequency
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More Common NamesContain Benzene
O
C - OH
O
O - C - CH3
AspirinAcetasalicyclic acid
OH
phenol
O
C - OH
Benzoic acid
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biphenyl
naphthalene anthraceneCl
p - dichlorobenzene
NH2
anilinephenylamineaminobenzene
Cl
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CH3
toluene
CH3
2,4,6 - trinitrotolueneNO2
NO2
O2N
TNT
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Dicarboxylic Acids
Oxalic Acid
O O
H O C C O H
Malonic Acid
O O
H O C CH2 C O H
Succinic Acid
O O
H O C CH2 CH2 C O H
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Dicarboxylic Acids
Glutaric Acid
O O
H O C CH2 CH2 CH2 C O H
Adipic Acid
O O
H O C CH2 CH2 CH2 CH2 C O H
Oh My Such Good Apples