Académique Documents
Professionnel Documents
Culture Documents
Structure Forms
C3H8
Kekul or Wedge/dash
H H
CH3CH2CH3
condensed
H H H
Classes of Hydrocarbons
Organic Compounds
hydrocarbons (C,H)
aliphatic (fatty)
alkane C C
alkene C C
alkyne C C
cyclic
Functional Groups
A functional group is an atom or group of atoms that have a characteristic chemical behavior. The chemistry of every organic molecule, regardless of size and complexity, is determined by the functional groups it contains.
Functional Groups
O C H3 C O O C O
5
Alkenes have a C-C double bond Alkynes have a C-C triple bond Arenes have special bonds that are represented as alternating single and double C-C bonds in a sixmembered ring
6
Functional Groups
Alkyl halide
H H C H H C H H C H H C H Br
Functional Groups
Alcohols
H H C H H C H H C H H C H OH
Functional Groups
Ethers
H H C H H C H H O C H H
Functional Groups
Aldehydes
H O H C H
10
C H
Functional Groups
Ketone
H O H H C C C H
H H Propanone (acetone)
11
Functional Groups
Carboxylic acids
H O H C H
Ethanoic acid (acetic acid)
12
C OH
Functional Groups
Ester
H H C H
O C O CH3
Functional Groups
Amine
H H C H
Methylamine
NH2
14
Functional Groups
Amide
O H3 C C NH2
Ethanamide (acetamide)
15
Functional Groups
Acid anhydride
O H3 C
O CH3
C O C
Ethanoic anhydride
16
Functional Groups
Acid halide
O H3 C C Cl
Ethanoyl chloride
17
Functional Groups
Nitro
O H3 C N O
18
Nitromethane
Functional Groups
Arene
benzene
19
Functional Groups
Halide
H3 C
Cl
Chloromethane
20
Functional Groups
Nitrile
H3 C
C N
Ethanenitrile
21
Functional Groups
Sulfide
H3 C
CH3
22
Functional Groups
Thiol
H3 C
Methanethiol
23
Functional Groups
O OCH3 O N H HO O
24
NH2
Alkanes: Compounds with C-C single bonds and C-H bonds only (no functional groups) Connecting carbons can lead to large or small molecules The formula for an alkane with no rings in it must be CnH2n+2 where the number of Cs is n Alkanes are saturated with hydrogen (no more can be added They are also called aliphatic compounds
25
Alkanes
H3C CH2 CH2 CH3 H H H H H C C C C H H H H H CH3CH2CH2CH3 H C H H C H H CH3(CH2)2CH3
H H C H
H C H
CH3CH(CH3)CH2CH3
26
Structure
Shape
27
Alkane Isomers
CH4 = methane, C2H6 = ethane, C3H8= propane The molecular formula of an alkane with more than three carbons can give more than one structure C4 (butane) = butane and isobutane C5 (pentane) = pentane, 2-methylbutane, and 2,2dimethylpropane Alkanes with Cs connected to no more than 2 other Cs are straight-chain or normal alkanes Alkanes with one or more Cs connected to 3 or 4 Cs are branched-chain alkanes
28
Alkanes
H C H H
29
Alkanes
branched chains
H H H H H H H H C C C C C H H H H H H H C H H H H H C C C C H H H H H H C H H H H C C C H H H H C H H
30
n-butane
H H C H
H C H
H C H
H C H H
C4H10
isobutane
C4H10
32
next draw all structures with 5 carbons in the longest chain (substitute for the H s)
then substitute for other H s
H H C H H H H C C C H H H H C H H C H H
33
34
35
Isomers
36
Constitutional Isomers
Isomers that differ in how their atoms are arranged in chains are called constitutional isomers Compounds other than alkanes can be constitutional isomers of one another They must have the same molecular formula to be isomers
37
Constitutional Isomerism
Molecular Cons titutional Formula Isomers CH 4 C 5 H12 C 10 H22 C 15 H32 C 30 H62 1 3 75 4,347 4,111,846,763
38
Alkyl Groups
Alkyl group remove one H from an alkane (a part of a structure) General abbreviation R (for Radical, an incomplete species or the rest of the molecule) Name: replace -ane ending of alkane with -yl ending
40
Classified by the connection site (See Figure 3.3) a carbon with one carbon attached to it (primary alkyl group) a carbon with two carbons attached to it (secondary alkyl group) a carbon with three carbons attached to it (tertiary alkyl group) a carbon with four carbons attached to it (quaternary alkyl group)
41
a carbon with one carbon attached to it (primary alkyl group) a carbon with two carbons attached to it (secondary alkyl group) a carbon with three carbons attached to it (tertiary alkyl group) a carbon with four carbons attached to it (quaternary alkyl group)
CH3
42
Degree of Substitution
CH3
1 3
4 CH 3
Nomenclature
colloquially: eye-you-pac
44
Naming Alkanes
Prefix-Parent-Suffix Named as longest possible chain Carbons in that chain are numbered in sequence substituents are numbered at their point of attachment Compound name is one word (German style) Complex substituents are named as compounds would be
45
Nomenclature Prefix-Parent-Suffix
CH2 CH3
octane
47
Nomenclature
Name Methane Ethane Propane Butane Pentane Hexane Heptane Octane Nonane Decane Undecane Dodecane
Condensed Structure CH4 CH3CH3 CH3CH2CH3 CH3(CH2)2CH3 CH3(CH2)3CH3 CH3(CH2)4CH3 CH3(CH2)5CH3 CH3(CH2)6CH3 CH3(CH2)7CH3 CH3(CH2)8CH3 CH3(CH2)9CH3 CH3(CH2)10CH3
48
C -C C- C-C-C -C-C-C-C-C C C
C -C C-C-C- C-C-C-C-C-C
49
Nomenclature
Parent name of the longest carbon chain is alkane Groups attached to the parent chain are called substituents Each substituent is given a name and a number
50
Nomenclature
Number the chain to give the substituent encountered first the lowest number If there are different substituents, list them in alphabetical order. The following are not included in alphabetization.
di-, tri-, tetra-, etc. hyphenated prefixes, such as sec- and tert-
51
Nomenclature
Alkyl groups
52
Nomenclature
Alkyl groups
Name pentyl isopentyl Condens ed Structural Formula -CH 2 CH2 CH 2 CH 2 CH 3 -CH 2 CH2 CHCH3 CH 3 CH3 neopentyl -CH 2 CCH 3 CH3
53
Nomenclature
CH 2 CH 3 CH3CH2CH2CH CH3
CH3 CH2 H3C CH CH CH2CH 3 CH2CH 2CH3
hexane
heptane
54
Nomenclature
If two different chains of equal length are present, choose the one with the larger number of branch points.
Nomenclature
Begin at the end nearer the first branch point (lower number).
1 2
CH3 CH2
3 4
H 3C
Nomenclature
If branching is equal distant away from both ends of the parent chain, begin at the end nearer the second branch point.
Nomenclature
Assign a number to each substituent according to its point of attachment to the main chain.
3-ethyl-4,7-dimethylnonane
58
Nomenclature
If there are two substituents on the same carbon, assign them both the same number.
4-ethyl-2,4-dimethylhexane
59
Nomenclature
Write the name as a single word, using hyphens to separate the different prefixes and commas, to separate numbers. Use di-, tri-, etc. if more than one identical substituents Dont use these prefixes for alphabetizing purposes.
60
Nomenclature
3-methylhexane
Nomenclature
4-ethyl-3-methylheptane
62
Nomenclature
3-ethyl-2-methylhexane
Nomenclature
Name a complex substituent and begin numbering at the point of attachment and set it off in parentheses.
Nomenclature
2,3-dimethyl-6-(2-methylpropyl)decane 2-methylpropyl CH3 1
CH3CH CHCH2CH2CH CH2CH CH3 CH3 CH3 CH2CH2CH2CH3
65
CH 3 CH 3
Nomenclature
CH CHCH 3
1,2-dimethylpropyl
2-methyl-5-(1,2-dimethylpropyl)nonane
66
Nomenclature-Historical
CHCH3
isopropyl (i-pr)
CH3
67
Nomenclature-Historical
Fourcarbon groups:
CHCH2CH3 CH3
CH2CHCH3 CH3
sec-butyl
isobutyl
tert-butyl
68
Nomenclature-Historical
CH2CH2CHCH3 CH3
isopentyl
Nomenclature
70
CH3 CH3
4-isopropyl-2,6,6-trimethylnonane
CH3CH2
2-cyclobutyl-5-methylhexane not (1,4-dimethylpentyl)cyclobutane
CH3
CH3
5-ethyl-1,1,3-trimethyl-2-(2methylpentyl)cyclohexane
72
Properties of Alkanes
Called paraffins (low affinity compounds) because they do not react as most chemicals They will burn in a flame, producing carbon dioxide, water, and heat They react with Cl2 in the presence of light to replace Hs with Cls (not controlled)
73
Physical Properties
Boiling points and melting points increase as size of alkane increases Forces between molecules (temporary dipoles, dispersion) are weak
74
The dependence of the boiling and melting points on chain length can be explained in terms of increasing attractive van der Waals interactions as the chain length increases.
75
Cycloalkanes
Cycloalkanes are alkanes that have carbon atoms that form a ring (called alicyclic compounds) Simple cycloalkanes rings of CH2 units, (CH2)n, or CnH2n Structure is shown as a regular polygon with the number of vertices equal to the number of Cs (a projection of the actual structure)
Cycloalkanes
77
Cycloalkanes
CH2OH CO H3C OH H O H
cortisone
78
O H3C
Cycloalkanes
to name, prefix the name of the corresponding openchain alkane with cyclo-, and name each substituent on the ring if only one substituent, no need to give it a number if two or more substituents, number from the substituent of lowest alphabetical order where there is choice, number to give substituents the lowest set of numbers
79
Naming Cycloalkanes
Count the number of carbon atoms in the ring and the number in the largest substituent chain. If the number of carbon atoms in the ring is equal to or greater than the number in the substituent, the compound is named as an alkyl-substituted cycloalkane For an alkyl- or halo-substituted cycloalkane, start at a point of attachment as C1 and number the substituents on the ring so that the second substituent has as low a number as possible. Number the substituents and write the name
80
Nomenclature
For alkyl-substituted cycloalkanes, start at the point of attachment and number the substituents on the ring so as to arrive at the lowest sum.
CH 3
1 6 5 4 2 3
Nomenclature
Br
CH3CH2
CH 3
82
1-bromo-2-methylcyclobutane
Rotation about C-C bonds in cycloalkanes is limited by the ring structure Rings have two faces and substituents are labeled as to their relative facial positions There are two different 1,2-dimethyl-cyclopropane isomers, one with the two methyls on the same side (cis) of the ring and one with the methyls on opposite sides (trans)
83
Stereoisomers
Compounds with atoms connected in the same order but which differ in three-dimensional orientation, are stereoisomers The terms cis and trans should be used to specify stereoisomeric ring structures Recall that constitutional isomers have atoms connected in different order
84
Cis-Trans Isomerism
H3 C CH3
H3 C CH3
85
Cis-trans isomerism
1,2-dimethylcyclopentane
H H H
H H H
H H H
H CH3 H
CH3 H trans-1,2-dimethylcyclopentane
86
Cis-trans isomerism
1,4-Dimethylcyclohexane
H H3 C trans -1,4-Dimethylcyclohexane
87