organic. kinds of hydrocarbons aliphatic –chains or rings of carbon atoms –may be planar or non...
TRANSCRIPT
Organic
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
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 -
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
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
Alkynes• Unsaturated hydrocarbons• Contain one triple bond• Naming
– Root name + yne
• General Formula: CnH2n-2
H
H C C C H
H
CH3CCH
propyne
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
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
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
Functional Groups
Oxygen Containing
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
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
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
Ester O
R - C - O R’
Naming R ’ alkyl + root name + bonding + oate
O
CHe CH2 CH2 C O CH2 CH3
ethyl butanoate
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
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
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
Common Substituents
- Cl chloro
- Br bromo- I iodo
- NO2 nitro- NH2 amino
- OH hydroxy
- R alkyl (hydrocarbon added to primary chain)
Common names of some organic substituents
CH3
CH
CH3
isopropyli - propyl
CH3
CH CH2
CH3
isobutyli - butyl
CH3
H3C C
CH3
tertiary butylt - butyl
CH2 CH vinyl
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
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
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
What is the BEST name for:
(CH3CH2)2NH
A)Ethyl amideB)DimethylamineC)1,1-ethylamineD)DiethylamineE)diethylamide
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
acetaldehyde O
CH3 - C - H
formaldehyde O
H - C - H
Formic acid O
H - C - O - H
(di)ethylether CH3CH2OCH2CH3
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
NO2 NO2 NO2
O O O
CH2 - CH - CH2
nitroglycerine
urea O
H2N C NH2
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
Benzene is represented by
Naming monosubstituents
CH2CH3
ethylbenzene
R
alkylbenzene
Cl
chlorobenzene
NH2
aminobenzeneaniline
NO2
nitrobenzene
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
Br
Br
1,4 - dibromobenzene
para - dibromobenzene
p - dibromobenzene
Br
NO2
1,3 - bromonitrobenzene
meta - bromonitrobenzene
m - bromonitrobenzene
If benzene is used as an attachmentIt is called phenyl
CH3
CHCH3
2 - phenylpropane
Fused benzene rings - share 2 C’s
Polycyclic compounds
naphthalene anthracene
/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
More Common NamesContain Benzene
O
C - OH
O
O - C - CH3
AspirinAcetasalicyclic acid
OH
phenol
O
C - OH
Benzoic acid
biphenyl
naphthalene anthraceneCl
p - dichlorobenzene
NH2
anilinephenylamineaminobenzene
Cl
CH3
toluene
CH3
2,4,6 - trinitrotolueneNO2
NO2
O2N
TNT
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
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