Physical Properties of Organic Compounds

Alkanes
Melting and boiling points increase with increasing molecular weight within a homologous series.
Compound Formula MW (g/mol) 16 72 142 212 282 mp (C) bp (C)

Methane Pentane Decane Pentadecane Eicosane

CH4 CH3(CH2)3CH3 CH3(CH2)8CH3 CH3(CH2)13CH3 CH3(CH2)18CH3

182 130 30 10 37

164 36 174 271 343

Physical Properties of Organic Compounds

Physical Properties of Organic Compounds

Physical Properties of Organic Compounds

Alkanes
Boiling points decrease with chain branching.

Compound CH3 CH3

octane

mp (oC) 57

bp (oC) 127 118

CH3 121 CH3

4-methylheptane

CH3

CH3 CH3 CH3

CH3 CH3 107 99

2,2,4-trimethylpentane

Physical Properties of Organic Compounds

Alkanes
Solubility Like dissolves like Alkanes are nonpolar, hydrophobic They are soluble in nonpolar solvents and insoluble in water.

Physical Properties of Organic Compounds

Compound CH3 Cl CH3
x ne

MW 6. . 6

p (oC) 6 3

H2O solubilit insolubl 0. %

Cl
loroet ne

1,2-di

O CH3 O CH3 86.09 88 20%

2,3-but nedione

Physical Properties of Organic Compounds

Compound O
dimet ox et

MW CH3 OH 90.12 90.12 88.15

bp (oC) 83 230 158

H 2O solubilit

CH3 HO

g g g

ne

1, -but nediol

H 2N CH3 H N

NH2
putres ine

N,N'-dimet

let

lenedi mine

CH3 88.15 N H

119

Physical Properties of Organic Compounds

Which of the following has the highest boiling point?
CH3CH2 CH CH3 CH3CH2 CH CH3 2. NH2 CH3CH2 CH CH3 3. OH

1. 4.

CH3

CH3CH2 CH CH3 Cl

5.

CH3CH2 CH CH3 CH2CH3

Physical Properties of Organic Compounds

Physical Properties of Organic Compounds

Isomerism
Isomerism The phenomenon whereby certain chemical compounds have structures that are different although the compounds possess the same elemental composition. Isomers Two or more chemical substances having the same elementary composition and molecular weight but differing in structure.

Isomerism
Consider C4H10 H H H H H H C C C C H H H H H H H H Normal Butane Isobutane H H C H H

H C C C H

ISOMERS

STRUCTURAL

OPTICAL

CONFIGURATIONAL

CONFORMATIONAL

Skeletal Functional Positional Tautomers

Compounds w/ same molecular formula but w/ structures that are mirror image of the other Rotate plane of polarized light equally but in opposite direction

Enantiomers chiral, non-superimposable mirror images Diastereomers nonsuperimposable, nonmirror images Anomers Epimers - different in geometry

Same stereochemical configuration but differing in 3D conformation

Constitutional Isomers-skeletal
C 4H 10

C 5H 12

Constitutional Isomers-skeletal
C 6H14

Constitutional Isomers-skeletal

Constitutional Isomers-skeletal
O H O H

OH

OH

Constitutional Isomers-positional
OH OH

HO

OH

HO

OH

Constitutional Isomers-functional
OH O

O H

Conformational Isomers

Conformational Isomers
H
U

H St ggered U = 60 o H H

=
H

H H

=
HH H H

Ecli U

Conformational Isomers

Conformational Isomers

60

120

180

E rel

0.9 kc al/mol

3.4 kcal/mol 0 kcal/mol

6.1 kcal/mol

Which is the most stable conformation for 1chloropropane about the C1-C2 bond?
CH 3 CH 3 Cl H H H CH 3 CH 3 H H Cl Cl CH 3 Cl H H H H H

1.

2.

H H

3.

4.
H Cl

5.
H