2

: , , ,
.
.
: , .
) ,(hydrocarbons .
Straight chain alkanes )
(.
Homologous series " .(methylene) CH2
) .(homolog - ) (CH3CH2CH3 ) (CH3CH2CH2CH3 .
CnH2n+2 :
, )
4 ( .
3 .
. 2 :C4H10
.1 .
.2 .

. .
)
(CH3 " ."iso ,
4 "".
. 3 :C5H12
.1
.2 iso 5-.
.3 " :"neo 4- .
. 5 ) C6H14
.1,2,3
(:
.1 .
.2 iso 6- ).(2-methylpentane
.3 neo 6- ).(2,2-dimethylbutane
3-methylpentane .4
2,3-dimethylbutane .5
. 9 .C7H16 : )
3 4- , (.
' ' ." ,
. ,
.
Systematic Nomenclature -IUPAC Nomenclature .
1

 , .common names
(1 :
) ' (.
" " "ane ."yl"- " "R .
.CnH2n+1 :
:
":
OH
NH2

R OH
R NH2
R X

F,Cl, Br, I = X

) , '(
.
:
.
?
, , 3.
.

.
.
.
3 -.

CH3CHCH3

CH3CH2CH2

An isopropyl group

a propyl group

CH3CHCH3

CH3CH2CH2Cl

Cl
Isopropyl chloride

Propyl chloride

. , ) isopropyl
(chloride :
, :
, . ,
. ) , , (
. 90 - ,
.
4 :
butyl, isobutyl .
sec-butyl ) .(S
tert-butyl ) .(T
" ") "n ,(normal .
, " "sec ." sec-butyl"- " " sec-pentyl
2 ,
. 2 , .
2

 , " "tert "tert-butyl" - "tert-pentyl" - .

" "tert-hexyl 2
.
,
: , .
.
.
.

:
" ,"iso " "iso
, )OH,NH2
'(.
" "iso .
) ,Cl ,OH' (.. ,
) .
" -"sec-propyl
" "iso . ,
isopropyl " "sec sec-"-
(."butyl
(2 :
" :
.1 . .
" " . , 8
) .(octane !
1

CH3CH2CH2CHCH2CH2CH3
8

CH3CH2CH2CH2CHCH2CH3

CH3

CH2CH2CH3

CH2CH2CH2CH3
6

CH3CH2CH2CH2CHCH2CH2CH3

.2 . ,
, " " .
' . ) (- . ,
common names , .
CH3
CH3CHCH2CH2CH3
common name: isohexane
systematic name: 2-methylpentane

CH3CH2CH2CHCH2CH2CH2CH3
CHCH3
CH3
4-isopropyloctane

CH3CHCH2CH2CH3
CH3
2-methylpentane

 .3 .ABC- ,
) ( . ,ABC-
.
CH3CH2CHCH2CHCH2CH2CH3

5-ehtyl-3-methyloctane
not
4-ethyl-6-methyloctane
because 3<4

CH2CH3

CH3

2 , " "tri","di' " .

" .
) . di, tri, tetra, sec, tert : , ABC -
.(iso, neo, cyclo
CH3

CH3 CH3

CH2CH3

CH3CH2CHCH2CH2CHCHCH2CH2CH3
CH2CH3

CCH2CH3

CH3CH2CH2C

CH3CH2CHCH2CHCH3
CH3

CH3 CH3

CH2CH3

2,4-dimethylhexane

3,3,4,4-tetramethylheptane

3,3,6-triethyl-7-methyldecane

CH3

.4 ' ,
.
CH3
CH3

CH2CH3

CH3CHCH2CHCH3

CH3CH2CHCHCH2CHCH2CH3

CH3

CH3

CH3

2,2,4-trimethylpentane
not
2,4,4-trimethylpentane
because 2<4

6-ethyl-3,4-dimethyloctane
not
3-ethyl-5,6-dimethyloctane
because 4<5

.5 , ABC - .
Cl

CH2CH3

CH3CH2CHCH3

CH3CH2CHCH2CHCH2CH3

Br

CH3

2-bromo-3-chlorobutane
not
3-bromo-2-chlorobutane

3-ethyl-5-methylheptane
not
5-ethyl-3-methylheptane

.6 - , .
6

CH3CH2CHCH2CH2CH3

2 CHCH3

CHCH3
CH3
3-isopropylhexane
)(one substituent

CH3CH2CHCH2CH2CH3

NOT

1 CH3

3-ethyl-2-methylhexane
)(two substituents

.7 "sec-butyl" ,"tert-butyl" : "isopropyl"- ,IUPAC .

" . ,
' 1 . :
, . .
CH3CH2CH2CH2CHCH2CH2CH2CH2CH3
CH2CHCH3
CH3
5-isobutyldecane
or
5-(2-methylpropyl)decane

CH3CH2CH2CH2CHCH2CH2CH3
CHCH3
CH3
4-isopropyloctane
or
4-(1-methylethyl)octane

 (3 :
.
, .
.CnH2n :
" " "cyclo .
.Skeletal structures , - ,
. . ,
4.
" : " -.
, , .
:
.1 , .
, , . .
CH2CH2CH2CH2CH3

CH2CH3
CH3

ethylcyclohexane

1-cyclobutylpentane

methylcyclopentane

.2 2 , " ABC 1 .
CH3

H3CH2C

CH3
1,3-dimethylcyclohexane

H 3C

CH3

CH2CH2CH3

1-ethyl-3-methylcyclopentane

1-methyl-2-propylcyclopentane

.3 2- , " . ABC 1
. ,
' , .
CH3

CH3CH2CH2

CH3
CH3
1,1,2-trimethylcyclopentane
not
1,2,2-trimethylcyclopentane
because1<2
not
1,1,5-trimethylcyclopentane
because 2<5

CH2CH3

H 3C

4-ethyl-2-methyl-1-propylcyclohexane
not
1-ethyl-3-methyl-4-propylcyclohexane
because2<3
not
5-ethyl-1-methyl-2-propylcyclohexane
because 4<5

 (4 -:
.
, .
.
.
.
) " (.
) (common - ,
" "ine "."ide
,IUPAC- .
" ."o:
CH CHI
CH CH CHBr
2

CH3

Br

CH3CH2F

CH3

fluoroethane

CH3Cl

chloromethane

2-iodopropane

2-bromobutane

I
CH3

CH3

CH2CH3

Cl

CH3CH2CHCH2CH2CH2Cl

CH3

CH3

4-bromo-2-chloro-1-methylcyclohexane

1-ethyl-2-iodocyclopentane

CH3CH2CHCH2CH2CH2CH3
Br
2-bromo-5-methylheptane

1-chloro-5,5-dimethylhexane

(5 ) : (
. - .,
.
R O R
R O R


) (common ,ABC
" ."ether .:
CH3

CH3CH2CH2CH2O

CH3

CH3CHOCHCH2CH3

CH3CH2CHOCCH3

CH3

cyclohexyl isopentyl ether

CH3

sec-butyl isopropyl ether

CH3CH2OCH2CH3

CH3OCH2CH3

diethyl ether

ethyl methyl ether

CH3

tert-butyl isobutyl ether

,IUPAC .RO " " "yl

"."oxy
CH3
CH3CH2O
CH3
tert-butoxy

CH3CH2CHO

CH3
sec-butoxy

CH3CH2O
CH3
isopropoxy

CH3CH2O
ethoxy

CH3O
methoxy

 (6 :
.OH
, OH-
.
R

R C OH

R CH OH

R CH2 OH

a secondary

a primary

R
a tertiary

) (common ,OH- .alcohol

OH- . ,IUPAC .
, " " "e " ,"ol
" .
CH3CH2CHCH2CH3

CH3CH2OH

CH3

OH
3-pentanol or
pentan-3-ol

ethanol

methanol

' :
.1 .
1

CH3CH2CH2CH2OCH2CH2CH2OH

CH3CH2CH2CHCH2OH

3-butoxy-1-propanol
or
3-butoxypropan-1-ol

CH3CHCH2CH3

CH2CH3

OH
2-butanol
or
butan-2-ol

2-ethyl-1-pentanol
or
2-ethylpentan-1-ol

.2 .
, .
1

CH3
4 3

CH3CCH2CHCH3

ClCH2CH2CHCH3

HOCH2CH2CH2Br

CH3 OH
4,4-dimethyl-2-pentanol

OH
4-chloro-2-butanol

3-bromo-1-propanol

.3 ,
CH3
,
.
.1
CH3CH2CH2CHCH2CHCH3

OH
3-methylcyclohexanol
not
5-methylcyclohexanol

CH3

OH

2-methyl-4-heptanol
not
6-methyl-4-heptanol

CH3CHCHCH2CH3
Cl OH
2-chloro-3-pentanol
not
4-chloro-3-pentanol

 .4 , " .ABC
HO
CH2CH3

CH3

CH2CH3
CH3CHCH2CHCH2CHCH3

OH

CH3

H3C

OH

2-ethyl-5-methylcyclohexanol

3,4-dimethylcyclopentanol

Br

6-bromo-4-ethyl-2-heptanol

: , .
] [ >= ] [ >= ][
(7 :
.
, .
R

R NH

RNR
a tertiary amine

R NH2

a secondary amine

NH3
ammonia

a primary amine

: , . ,
, OH .
R

R C OH

R C Cl

R C NH2

a tertiary alcohol

R
a primary amine

a tertiary alkyl chloride

,ABC " ."amine

) , (] . " [78
IUPAC " . " "e
) "amine"- (.
. ."amine"-
" "N .
ABC " "N .
.
1

CH3CH2CH2NCH2CH3
CH3
N-ethyl-N-methyl-1-propanamine
or
N-ethyl-N-methylpropan-1-amine

CH3CH2CHCHCH2CH3
NHCH2CH3

N-ethyl-3-hexamine
or
N-ethylhexan-3-amine

CH3CH2CH2CH2NH2
1-butanamine
or
butan-1-amine

CH2CH3
1

NHCH2CH2CH3

Br

CH3CHCHCHCH3
N
CH3

2-ethyl-N-propylcyclohexanamine

CH3

4 5

CH3CH2CHCHCHCH3
NHCH2CH3

H3C

4-bromo-N,N-dimethyl-2-pentanamine

N-ethyl-5-methyl-3-hexanamine

CH3CHCH2CH2NCH3
Cl
3-chloro-N-methyl-1-butanamine

Quaternary ammonium salts 4 - .

ABC "."ammonium
CH3
Cl-

CH3

N+

CH3
CH3CH2CH2

HO-

CH3

ethyldimethylpropylammonium chloride

CH3

N+

H3C

CH3
tetramethylammonium hydroxide

(8 - , , :
: X) C-X ( -
sp sp .
, C-X
.
: .

. .sp
sp sp ,
s sp
-.

 : .
.
: .

.9 ,- , , :

. :Boiling point
)(.
.
- . - , .
" , .
" . ,
, . , .
, . ,
, .
. ,
. ,
- .induced-dipole interactions
" Van der -
.Waals forces - .
) , ,- (
, -- .
, -- . . ,
-- , .
' , .
, . ,
) (25C .
-- ,
. - .
: , .
" ) C-Z Z ,F ,O ,N
,Cl ,(Br , .
10

 " .
. dipole-dipole
:interactions -- .
, ,
-- - " .
-- -
,C-O .
- , N ,O - F
,N ,O F .
- , .
:
. ,
, .

,
. ,
.
N-H ,
. .
, :
< <
'
" - -- - . ,
. , )= -- ( polarizability- .
:Polarizability ) (.
, , .
polarizable -- . ,
.

.' :Melting point

11

 . , ) (
.
/ .
:Packing . ,
.
:


. ' -
' . '

" . ,
' -
.

. :Solubility
" ,"like dissolves like":"
, .
) ( .
,
.
, .
"."solvation
, ." ,
, . .
,
- -.

, .
, 30 .
) . ,
(.
OH . ?
. ,
. , .
: 4- , 4- .
, OH .
,
.
, . tert-butyl
. n-butyl
, 3 - .
.
, . :
, .
, , )
(.
< <
12


- , Alkyl fluorides- ." -
.- ' .
.9 : -
- ) ( sp3 sp3 .
)" ( , C-C
.
-Conformations .
.Conformer
- 2 , staggered conformation--
.eclipsed conformation .
, . , see-
saw " ,
.
, , ,
.
,see-saw - .
, - . " ,
" . .
C-H C-H .
staggered conformation - C-H .
eclipsed conformation - C-H
. ) torsional strain / (.
Torsional strain
.
.conformational analysis
- eclipsed- -
.staggered , -
. , ,

. ,
.
,
.360
staggered - ,
eclipsed - .
3 - , .
staggered - eclipsed - -1 2.
staggered - C1-2 , -
staggered C2-C3 .

13

 ,C , A E
.staggered
,C , .anti conformer anti conformer .
A , ,E- .gauche conformers gauche conformer
. gauche conformers - .anti conformer -
anti gauche - .steric strain -
Steric strain ) ( ,
. , steric strain gauche
anti .gauche
eclipsed -
C2-C3 . -
eclipsed
) (F eclipsed -
) .(D,B
C2-C3
.
eclipsed - ) torsional strain ( ) steric strain - (.
steric strain , .
- , -
- .
.
. ,
. , staggered ,eclipsed
anti .gauche

.11 :
5 6 3 4 . 5 6
3 4.
3 4 ) .(angle strain sp3
.109.5 "
. ,60 3 .60
49.5 , .
" . "
sp3 . , ,
. , C-C C-C .
C-C , ,
14

 ,
torsional strain C-H .eclipsed

109.5 - ,90 - 4 . ,
, 19.5 - .
, ) (120 ) ,(108
. . 3
, , "
:
.1 .109.5
torsional strain .2 .
steric strain .3 .
, torsional strain
4 ,eclipsed . ,
- . ) 25( "
. torsional -
) strain eclipsed (.
, , 10
torsional strain . " .staggered,
, . .
.12
6
. . , ,111
- .109.5 .staggered

:
.1 , .
.2 .V V- , . V- ,
V- . .
.3 Axial bond .
. , , .
15

 Equatorial bonds .4 , .
,90 - .
.
.

.

.

,

.

, ) (steric + strain +
. " .

- .
.ring flip- ,

,
.
. ,
.
,eclipsed torsional -
.strain , ) flagpole hydrogens- ( , -
.steric strain
,
. , .twist boat conformer
eclipsing ,torsional strain flagpole- , steric -
.strain
.half-chair conformer :
. .
ring-flips 510 - , 2 " .
16

.
.13 :
2 ,
.
,
.

, ,
) (steric .

, C-3 .C-5 ,
, .
, ,
C-3 ,C-5 . ,
) (steric
. ,
,
. "
,1,3 1,3-
.diaxial interactions
) (gauche gauche
.anti - 2 gauche
, 2 .
2 ,
. 2
. ,diaxial hydrogens -
1,3-diaxial . ,
.
.14
2 , .
:1,4-dimethylcyclohexane 2 :
cis isomer 2 .
trans isomer 2 .
, / : .
H
H
17
CH3

CH3

Cis-1,4-dimethylcyclohexane
Trans-1,4-dimethylcyclohexane
Cis-1,4-dimethylcyclohexane
.
H
H

H
H 3C

CH 3

ring-flip

CH 3

cis-1,4-dimethylcyclohexane

CH 3

trans-1,4-dimethylcyclohexane
. 2 4
,1,3-diaxial 4
. , , trans-1,4-dimethylcyclohexane
.
CH 3

H
H

H
CH 3

ring-flip

H 3C

CH 3

trans-1,4-dimethylcyclohexane

:1-tert-butyl-3-methylcyclohexane
, .
.
.
tert-butyl , 1,3
diaxial tert-butyl
. , tert--
butyl .
.15
, . 2 ,
. , )
( . ,
.
H

18

19