3.1 functional groups - yonsei university · 2017-11-13 · ch.3 organic compounds: alkanes and...
TRANSCRIPT
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
functional groups: a group of atoms within a molecule that has a characteristic chemical behavior; a given functional group, regardless of size and complexity, behaves in nearly the same way
3.1 Functional Groups
• more than 19 million known organic compounds according to Chemical Abstracts
• classify into families with similar chemical behavior
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
H
H
H
H
HO
Ethylene
Cholesterol
Br2 H
H
H
H
HO
Br
Br
BrBr
Br2
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
Functional Groups
Alkane Alkene
C C
Alkyne
C C
Arene(aromatic ring)
C C
Functional Groups with C/C Multiple Bonds
C/C Multiple BondsC-Y (Y= electronegative atom: O, N, Cl, S...)C=O, C=N, C≡N
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
Functional Groups with C-Y (Y= electronegative atom)
Halide
XC
(X= F, Cl, Br, I)Alcohol
OHC
Ether
OC C
Amine
NH2C
SulfideThiol
SHC SC C
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
Functional Groups with C=O
Aldehyde
CC HO
Ketone
CC CO
Carboxylicacid
CC OHO
Ester
CC OO
C
Amide
CC NO
Carboxylicacid chloride
CC ClO
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
Table 3.1 Structures of Common Functional Groups
Familyname
Functional groupstructure
Simple example Name ending
Alkane contains only C-H and C-C single bonds CH3CH3
-aneEthane
Alkene C C CH2=CH2
-eneEthene
(Ethylene)
Alkyne C C-yne
Ethyne(Acetylene)
C CH H
Arene NoneBenzene
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
Table 3.1 Structures of Common Functional Groups
Familyname
Functional groupstructure
Simple example Name ending
Halide XC NoneChloromethane
ClH3C(X= F, Cl, Br, I)
Alcohol OHC -olMethanol
OHH3C
Ether OC -etherDimethyl ether
OH3CC CH3
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
Table 3.1 Structures of Common Functional Groups
Familyname
Functional groupstructure
Simple example Name ending
Amine NHC -amineMethylamine
NH2H3C
Nitrile CC-nitrile
Ethanenitrile(Acetonitrile)
CH3CN N
NCNH2C
Nitro NO2C NoneNitromethane
NO2H3C
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
Table 3.1 Structures of Common Functional Groups
Familyname
Functional groupstructure
Simple example Name ending
Sulfide -sulfideDimethyl sulfide
Thiol SHC -thiolMethanethiol
SHH3C
SC C SH3C CH3
Sulfoxide -sulfoxideDimethyl sulfoxideSC C SH3C CH3
O O
Sulfone -sulfoneDimethyl sulfoneSC C SH3C CH3
O O
O O
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
Table 3.1 Structures of Common Functional Groups
Familyname
Functional groupstructure
Simple example Name ending
Aldehyde-al
Ethanal(Acetaldehyde)
CC H CH3C H
O O
Ketone-one
Propanone(Acetone)
CC C CH3C CH3
O O
Carboxylicacid
-oic acidEthanoic acid(Acetic acid)
CC OH CH3C OH
O O
Ester-oate
Methyl ethanoate(Methyl acetate)
CC O CH3C O
O OC CH3
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
Table 3.1 Structures of Common Functional Groups
Familyname
Functional groupstructure
Simple example Name ending
Amide-amide
Ethanamide(Acetamide)
CC NH CH3C NH2
O OCC NO
CC NH2
O
Carboxylicacid chloride
-oyl chlorideEthanoyl chloride(Acetyl chloride)
CC Cl CH3C Cl
O O
Carboxylicacid anhydride
-oic anhydrideEthanoic anhydride(Acetic anhydride)
CC O CH3C O
O OCO
C C CH3
O
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Practice functional Groups
Ch.3 Organic Compounds: Alkanes and Cycloalkanes
O O
O
O
HO
Coleophomone A
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
alkanes: saturated hydrocarbon, : aliphatic compound (meaning "fat")
3.2 Alkanes and Alkane Isomers
H3C CH3CH4CH3CH2CH3
Methane Ethane, C2H6 Propane, C3H8
general formula: CnH2n+2
Butane Isobutane(2-Methylpropane)
C4H10
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
Pentane 2-MethylbutaneC5H12
2,3-Dimethylpropane
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
- straight chain alkanes (normal alkane) - branched chain alkane
isomer: same formula but different structureconstitutional isomer: connected differently
Pentane 2-Methylbutane 2,3-Dimethylpropane
C5H12
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Practice How many isomers ?
Ch.3 Organic Compounds: Alkanes and Cycloalkanes
C6H14
5
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
- constitutional isomerism is not limited to alkanes
Butane Isobutane(2-Methylpropane)
Different carbon skeletonC4H10
Ethyl alcohol
Different functionalgroupC2H6O
CH3CH2OH
Diethyl ether
CH3OCH3
Ethyl alcohol
Different position offunctional groupC3H9N
CH3CHCH3
Propylamine
CH3CH2CH2NH2
NH2
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
CC
CC
H CH
HCH
HCH
HCH
HH
H
H H
H H
H HH
H H
H3C CH2 CH2 CH3 CH3CH2CH2CH3
CH3(CH2)2CH3
- different ways to represent n-butane (n= normal); n-C4H10
these structures do not imply any specific geometry
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
Names of straight chain alkanes: ending -ane
12345678
MethaneEthanePropaneButanePentaneHexaneHeptaneOctane
910111213202130
NonaneDecaneUndecaneDodecaneTridecaneIcosaneHenicosaneTriacotane
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
alkyl group: partial structure of alkane (-H); used for naming purpose
3.3 Alkyl Groups
CH4
Methane
H3C
A methyl group
H3C OH
Methyl alcohol
H3C NH2
Methyl amine
Methyl (Me)
-CH3
Ethyl (Et)
-CH2CH3
Propyl (Pr)
-CH2CH2CH3
Butyl (Bu)
-CH2CH2CH2CH3
Pentyl, or Amyl
-CH2CH2CH2CH2CH3
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
Propyl (n-Pr) Isopropyl (i-Pr)
n-Butyl (n-Bu) sec-Butyl (s-Bu)
Isobutyl (i-Bu) tert-Butyl (t-Bu)
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
four possible degrees of alkyl substitution for carbon
CH
HR H C
H
RR H
CR
RR H C
R
RR R
primary carbon (1o) secondary carbon (2o)
tertiary carbon (3o) quartenary carbon (4o)
R = a generalized alkyl groupAr = a generalized aryl group
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
CH
HR OH C
H
RR OH C
R
RR OH
primary alcohol (1o) secondary alcohol (2o) tertiary alcohol (3o)
CH3CH2CHCH3
CH3
a tertiary hydrogen
secondary hydrogens
primary hydrogens
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
IUPAC: International Union of Pure and Applied Chemistry
3.4 Naming Alkanes
ParentPrefix Suffix
What family?How many carbons?Where are the substituents?
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
Step 1. Find the parent hydrocarbon.
hexane heptane
a) the longest continuous chain of carbon atoms
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
two substituents one substituents
b) if two different chains of equal length are present; choose the one with the larger number of branch points
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
Step 2. Number the atoms in the main chain.
a) beginning at the end nearer the first branch point
heptane
1
2 34 5
6
7
7
6 44 3
2
1NOT
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
192
345
67
8
3,4,7
b) if there is branching an equal distance away from both ends; begin the end nearer the second branch point
918
765
43
2
3,6,7
NOT
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
Step 3. Identify and number the substituents.
192
345
67
8
a nonane
3-ethyl4-methyl7-methyl
a) assign a number to each substituent according to its point of attachment to the main chain
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
12
345
6
a hexane
2-methyl4-methyl4-ethyl
b) If there are two substituents on the same carbon, give them both the same number.
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
Step 4. Write the name as a single word.
3
- use hyphens to seperate the different prefixes- use comma to seperate numbers- cite in alphabetical order- more than one identical substituents; di-, tri-, tetra-...
(Don't use these prefixes for alphabetizing purposes)
192
345
67
8
3- Methylhexane
3-Ethyl-4,7-dimethylnonane
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
Me
Et2 3 3-Ethyl-2-methylheptane
4-Ethyl-3-methyloctane
4-Ethyl-2,4-dimethylheptane
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
Step 5. Name a complex substituent just as though it were itself a compound.
19
23
4 5 67
810
2,3,6-trisubstituted decane
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
Molecule1
2 3
- begin numbering at the point of attachment
2-methylpropyl group
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
The substituent is alphabetized according to the first letter of its complete name (including any numerical prefix) and is set off in parentheses.
19
23
4 5 67
810
2,3-Dimethyl-6-(2-methylpropyl)decane
6-Isobutyl-2,3-dimethyldecane
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
19
23
4 5 67
8
1
23
5-(1,2-Dimethylpropyl)-2-methylnonane
5-(1,2-dimethylpropyl)
- alphabetizing the substituent: the first letter of the complete name(including any numerical prefix of the complex substituent)
2-methyl
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Practice IUPAC Name
Ch.3 Organic Compounds: Alkanes and Cycloalkanes
6-(1-Ethylbutyl)-3,5-dimethylundecane
6-(1-ethylbutyl)
6
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
common names: historical reason
Isopropyl (i-Pr)
sec-Butyl (s-Bu) Isobutyl (i-Bu) tert-Butyl (t-Bu)
three-carbon alkyl group
four-carbon alkyl group
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
Isopentyl or isoamyl (i-amyl)
Neopentyl tert-Pentyl ortert-amyl (t-amyl)
five-carbon alkyl group
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
common name and IUPAC name, both are used
Cautioniso, neo, cyclo are considered part of the alkyl-group for alphabetizing purposes but sec-, tert- are not.
4-(1-Methylethyl)octane
or 4-Isopropyloctane
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Practice IUPAC Name
Ch.3 Organic Compounds: Alkanes and Cycloalkanes
27
2,7-Dimethylnonane
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Practice IUPAC Name
Ch.3 Organic Compounds: Alkanes and Cycloalkanes
3-Isopropyl-2-methylhexane
3 32
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
3.5 Properties of Alkanes
• alkanes are sometimes referred to as paraffins (meaning "slight affinity"); little chemical affinity for other substances; chemically inert to most laboratory reagents
combustion
CH4 + 2 O2 CO2 2 H2O+ + 890 kJ/mol (213 kcal/mol)
• alkanes do react with oxygen, chlorine, and a few other substances under appropriate conditions
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
photochemical chlorination
CH4 + +Cl2hν CH3Cl HCl
Cl2 +CH2Cl2 HCl
Cl2 +CHCl3 HCl
Cl2 +CCl4 HCl
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
• b.p. or m.p. of alkane increases with molecular weight due to intermolecular dispersion forces (van der Waals forces) between molecules.; C1 - C4 (gas): C5 ~ (liquid)
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
Dispersion forces (van der Waals forces) : operate only very small distances, arise because the electron distribution in alkane molecule, although uniform over the time, is likely to be nonuniform at any given instant. One side of a molecule may, by chance, have slightly excess of electrons relative to the opposite side, giving the molecule a temporary dipole moment. This temporary dipole in one molecule causes a nearby molecules to adopt a temporarily opposite dipole, with the result that a tiny electrical attraction is induced between the two. Temporary molecular dipoles have a fleeting existence and are constantly changing, but the cumulative effect of an enormous number of them produces attractive forces sufficient to cause a substance to remain in the liquid or solid state.
δ− δ+ δ− δ+ δ− δ+
attractive van der Waals force
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
3.6 Cycloalkanes• cycloalkanes or alicyclic compound
Cyclopropane Cyclobutane Cyclopentane
Cyclohexane Cycloheptane Cyclooctane
general formula: CnH2n
• b.p.of cycloalkane increases with molecular weight; but, m.p. is affected by molecular weight and shape
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
HH CO2H
Chrysanthemic acid
(insecticidal)
OH
OH
HOHHHO
O
H
Prostaglandin E1 (PGE1)
(hormone which controlsblood platelet aggregation,bronchial dilation,inhibition of gastric secretion)
O
OH
OOH
OH
HH
Cortisone
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
3.7 Naming Cycloalkanes
; if the number of carbons of ring ≥ the number of carbons in the substituent: name as cycloalkane
CH3
Step 1. Find the parent.
Methylcyclopentane
1-Cyclopropylbutane
; if the number of carbons of ring < the number of carbons in the substituent: name as alkane
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
; for alkyl- and halo-substituted cycloalkanes: choose a point of attachment as C1 and number others so that the second substituent has as low a number as possible
1
3
Step 2. Number the substituents.
1
5
1,3-Dimethylcyclohexane NOT
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
MeMe
Et
1
24
; if second point is same, choose lowest third or fourth
MeMe
Et1
26
2-Ethyl-1,4-dimethylcycloheptane
MeMe
Et
4
31
MeMe
Et
NOT
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
(a) When two or more different alkyl groups that could receive the same numbers of present, number them by alphabetical priority.
Me
Et1
2Me
Et
1
2
1-Ethyl-2-methylcyclopentane
NOT
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
(b) If halogens are present, treat them exactly like alkyl groups
Me
Br1
2Me
Br2
1
1-Bromo-2-methylcyclobutaneNOT
bromo > methyl
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Practice IUPAC Name
Ch.3 Organic Compounds: Alkanes and Cycloalkanes
1-Bromo-3-ethyl-5-methylcyclohexane
Br
Et Me
1
3 5
Br
Et Me
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Practice IUPAC Name
Ch.3 Organic Compounds: Alkanes and Cycloalkanes
(1-Methylpropyl)cyclobutane
1
sec-Butylcyclobutane
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Practice IUPAC Name
Ch.3 Organic Compounds: Alkanes and Cycloalkanes
1-Chloro-3-ethyl-2-methylcyclopentane
ClMe
Et
1
2
3
ClMe
Et
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
3.8 Cis-Trans Isomerism in Cycloalkanes
• In many respects, the chemistry of cycloalkanes is like that of open-chain, acyclic alkanes; nonpolar, inert.
• But cycloalkanes are less flexible than acyclic alkanes.; free rotation is possible around C-C bond in open-chain molecules (because σ-bond is cylindrically symmetrical)
H
CH H
H
HHC rotate
HC
H
HH
HHC
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
H
HH
H
H
H
No rotation is possible around the C-C bonds withoutbreaking open the ring
• cycloalkanes (C3-C7) are severely restricted in their molecular motions• larger cycloalkanes have increasingly more rotational freedom• very larger ring (C25 and up) are so floppy that they are nearly indistinguishable from open-chain alkanes.
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
• Cycloalkanes have two sides, a "top" side and a "bottom" side, leading to the possibility of isomerism in substituted cycloalkanes.
H3C
HH
CH3
H
HH3C
HH
H
CH3
H
trans-1,2-Dimethylcyclopropane
X
cis-1,2-Dimethylcyclopropane
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
stereoisomer: atoms connected in the same order but differ in 3-dimensional orientation
Constitutional isomers(different connections between atoms)
H3C
HH
CH3
H
HH3C
HH
H
CH3
H
trans-1,2-Dimethylcyclopropanecis-1,2-Dimethylcyclopropane
Stereoisomers(same connections but different 3-dimensional geometry)
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Ch.3 Organic Compounds: Alkanes and Cycloalkanes
• cis-trans isomer
HH
H3C CH3
cis
Br
H
H
Et
trans
HO
H
OH
H
cis
H3C
CH3HH
Br HH Et
HO
OH
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Gasoline from PetroleumChemistry @ Work
natural gas and petroleum: derived from the decomposition of plant and animal matter, primarily marine origin
- natural gas : methane (major), ethane, propane, butane, isobutane
- petroleum : complex of hydrocarbons that must be refined into fractions before it can be used
refining by distillation of crude oil
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Gasoline from PetroleumChemistry @ Work
Petroleum
Asphalt Lubricating oils,waxes
Heating oil(C14 - C25)
Kerosene(C11 - C14)
Straight-run gasoline(C5 - C11)
Natural gas(C1 - C4)
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Gasoline from PetroleumChemistry @ Work
octane number: the measure by which its antiknock properties are judged
• straight-chain hydrocarbons are far more prone to induce engine knock than a highly branched compounds
CH3CH2CH2CH2CH2CH2CH3
Heptane(octane number = 0)
CCH3
CH3
CH2H3C CH
CH3CH3
Isooctane(octane number = 100)
bad fuel good fuel
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Gasoline from PetroleumChemistry @ Work
• straight-run gasoline: a high percentage of unbranched alkanes, poor fuel
catalytic cracking: "cracking" high-boiling kerosene (C11-C14) into smaller molecules suitable for use in gasoline; on silica-alumina catalyst, 400-500 oC; major products are C3-C5 carbons which are then catalytically recombined to C7-C10 alkanes