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dimethyl ether diethyl ether... Table 2.4 Carbon-—Halogen Bond Lengths and Bond Strengths interactions lengths kcal/mol kJ/mol... G: 3 hybridized gd." an alcohol electrostatic potent

two different ways to draw isopropyl chloride

| primary hydrogens | | tertiary hydrogen | | secondary hydrogens | CH;

dimethyl ether

diethyl ether

Table 2.4 Carbon-—Halogen Bond Lengths and Bond Strengths

interactions lengths kcal/mol kJ/mol

G: 3 hybridized

gd."

an alcohol electrostatic potential

map for methanol

a primary amine a secondary amine a tertiary amine

electrostatic potential maps for

methylamine dimethylamine trimethylamine

solvation of a polar compound

Òt+ O-

(Y— Z) by water

`

banana bonds

Physical Properties of Alkenes

57

—69

37 a7

83

Density (g/mL)

0.641 0.673 0.697 0.715 0.730 0.741 0.650 0.649 0.594 0.650 0.649 0.811

cyclobutane

cyclopentane

the methyl group is in

“C7” ring flip YX in an axial position

C Hà

Table 2.4 Carbon-—Halogen Bond Lengths and Bond Strengths

interactions lengths kcal/mol kJ/mol

CH,

CạHs CạHg CaHịo CzHì¡;

CoH 14 C;H1s CgHig CoH 29 CịoHa2 C¡iH2¿

C2H 6 C1 3H

heptane

octane nonane decane undecane dodecane tridecane

eicosane heneicosane

triacontane

Nomenclature and Physical Properties of Straight-Chain Alkanes

Boiling Condensed point

CH3CH3 —88.6 CH:CH›CH:a —42.1 CH:CH›CH›CH:a sates CH3(CH>)3CH3 36.1 CH3(CH)4CH3 68.7 CH3(CH>)5CH3 98.4 CH3(CH>),CH3 127.7 CH3(CH>)7CH3 150.8 CH3(CH>)gCH3 174.0 CH3(CH>)9CH3 195.8 CH3(CH>);9CH3 216.3 CHa(CH;)¡¡CH:a 235.4

CH3(CH>);3CH3 343.0 CH3(CH2),;9CH3 356.5 CH3(CH>)23CH3 449.7

“Density is temperature dependent The densities given are those determined at 20 °C (d?°’)

Melting point

(°C)

—182.5

=—183:3 Lol.)

65.8

Density“

(g/mL)

572 0.6603 0.6837 0.7026 0.7177 0.7299 0.7402 0.7487 0.7546

0.7886 0.7917

0.8097

Table 2.3 Summary of Nomenclature

Systematic name Alkyl halide substituted alkane

CH3Br bromomethane CH;3CH>CI chloroethane Ether substituted alkane

CH30CH3 methoxymethane CH3CH2OCH3 methoxyethane Alcohol functional group suffix is ol

CH30H methanol CH3CH,OH ethanol Amine functional group suffix is amine

CH3CH,NH> ethanamine CH3CH»CH»,NHCH3 N-methyl-1-propanamine

CH3CH,0OCH3 ethyl methyl ether alkyl group to which OH is attached, plus alcohol CH30H methyl alcohol

CH3CH>OH ethyl alcohol alkyl groups attached to N, plus amine CHaCH›NH;›; ethylamine

CH3CH»CH»NHCH3 methylpropylamine

Table 2.5 Comparative Boiling Points (°C)

Table 2.6 Comparative Boiling Points of Alkanes and Alkyl Halides (°C)

Table 2.7 Solubilities of Ethers in Water

CH;CH50CH>CH;

CH;CH,OCH>CH,CH;

CH;3CH>CH,OCH,CH>CH;

soluble soluble

slightly soluble (10 g/100 g HO)

minimally soluble (1.0 g/100 g HO)

insoluble (0.25 øg/100 g HO)

Table 2.8 Solubilities of Alkyl Halides in Water

Table 2.9 Heats of Formation and Total Strain Energies of Cycloalkanes

‘‘Strainless’’

Heat of formation heat of formation

(kcal/mol) (kJ/mol) (kcal/mol) (kJ/mol)

0 6.2 o7 12.6

123 J1”

(kJ/mol) 114.2 [10:9 25.9

0 202110) 40.6 a2)

515 46.9