כימיה אורגנית ופולימרים

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כל חומר הקורס כימיה אורגנית ופולימרים להנדסת מכונות במכללת אורט בראודה

Text of כימיה אורגנית ופולימרים

' 11

? . , , , . .

2

? . , , , . .

3

( ) 02 .

4

DNA V 5

TNT 6

C-C - C-H . 4 , . , ( ). 5.2, (, , ), ().

7

" . , "".8

: . , . . .9

. . 901. . .

01

: 4CH : : 05.901

11

: 4C2H : : 0021

21

: 2C2H : : 0081

31

: 6C3H

21C6H

41

"": 8C8H

51

, . : , , "" .R , .

61

R , . , , .

71

. : ) - CnH2n+2 :(Alkanes ( ). ) - CnH2n :(Alkenes . ) CnH2n-2 :(Alkynes . ) CnH2n :(cycloalkanes .81

C C

: )(Alkenes

C

C

: )(Alkynes91

-OH : )(AlcoholsO R H

R-OH : ( = R ))

-O : ):(EthersO R 'R

R-O-R

:02

)(X = F , Cl , Br , I -X

: Alkyl halides R-X :

):(Amines , 3.NH : 2R-NH : R-NH-R :

12

'R N R ''R

--CO . -.

C

O

.22

):-CHO (Aldehydes RCHO OR C H

):CO- (Ketones O R C 'R

32

):-COOH (Carboxylic acidsO R C OH

O R C 'OR

):COO- (Esters

42

):CONH- (Amides O 'R C NH R

52

2

. : ) - CnH2n+2 :(Alkanes ( ). ) - CnH2n :(Alkenes . ) CnH2n-2 :(Alkynes . ) CnH2n :(cycloalkanes .Molecular models

Alkanes . :2+CnH2n : : ane : 4Methane - CH

4CH

-

, ) (

), (

) (

Alkanes . :2+CnH2n : : ane 4Methane - CH 3Ethane - CH3CH

(C1 C10 ( Methane - CH4 Ethane - CH3CH3 Propane - CH3CH2CH3 Butane - CH3CH2CH2CH3 Pentane - CH3CH2CH2CH2CH3 Hexane - CH3CH2CH2CH2CH2CH3 Heptane - CH3CH2CH2CH2CH2CH2CH3 Octane - CH3CH2CH2CH2CH2CH2CH2CH3 Nonane - CH3CH2CH2CH2CH2CH2CH2CH2CH3 Decane - CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3

01C4H

3CH3CH2CH2CH

01? C4H

H H3C C CH3 CH3

H3C

CH2

CH2

CH3

Isobutane

n-butane (normal)

.

: , . : 01C4HH H3C C 3CH Isobutane 3CH

H3C

2CH

2CH

3CH

n-butane )(normal

()

4CH 6C2H 8 C3 H 01C4H 21C5H 41C6H 61C7H 22C10H 24C20H

1 1 1 2 3 5 9 57

4CH 6C2H 8 C3 H 01C4H 21C5H 41C6H 61C7H 22C10H 24C20H

1 1 1 2 3 5 9 57 913,663

: 21C5H 41C6H 1. 2.

, 2+CnH2n

: : 5.2 : 1.2 C-C H-C . . , --..

MW 4CH 01C4H 61C7H H2O 61 85 001 81 )bp (C 7.161- 5.0- 4.89 001 )mp (C 5.281- 5.831- 6.09- 0 )d(g/ml 664.0 106.0 486.0 00.1

2+CnH2n1= n 4= - n . 5= n 81= - n 81>n

261- 004 003 002 001( ) '

4CH 6C2H 01C4H 21C5H 41C6H 61C7H

24- 5.0- 63 96

0

001- 002-

0

001

002

003

89

: , . : . .

01C4H bp )(C 5.0- 7.11- mp )(C 3.831- 4.951- d )(g/ml 106.0 755.0

, . . : . .

21C5H bp )(C mp )(C d )(g/ml

1.639.72 4.9

8.921-9.951- 8.61-

626.0026.0 095.0

, "" . , .

() IUPACInternational Union of Pure and Applied Chemistry

. . . . .

CH3 Methyl CH3 CH2 Ethyl CH3 CH2 CH2 Propyl CH3 CH CH3 Isopropyl (1-Methylethyl) CH3 CH2 CH2 CH2 Butyl CH3 CH CH2 CH3 Isobutyl (2-Methylpropyl) CH3 CH3 CH2 CH CH3 sec-Butyl (1-Methylpropyl) CH3 C CH3 tert-Butyl (1,1-Dimethylethyl)

IUPAC ?1 2 3

3CH3CHCH 3CH

1. . 3 - .

2. / / : 3 - CH. 3. . 2 2-methylpropane : 2-

() IUPAC , .

IUPAC3CH3CH2CH2CH2CH(CH2CH3)CH(CH3)CH2CH

?1

2 7 6 5 4 3 8

8 : : : , . 4-ethyl-3-methyloctane

() IUPAC . , - , - , -, ' , .

IUPAC ?

2,3-dimethylpentane

CH3CH2CH2C(CH3)2CH(CH3)CH2CH33,4,4-trimethylheptane

IUPAC 4

12

.

4-tert-butyloctane 4-(1,1-dimethylethyl)octane

1,1,1,3,3,3-hexachloropropane 1,1,1,3,3,3-2

3Cl3C-CH2-CCl

BrH2C7

1 3 5 2 1

5-(2-bromoethyl)-2-methyloctane 5-(2-)-2-

8 6

4

3

:. : (). . , , .

:

((Naphtenes

)(Paraffines

)(Aromatics

(") 4-1 11 - 5 31 - 7 61 - 01 52 - 51 07 - 02 07

)Tb (oC - 03 021 - 03 002 - 001 052 - 051 053 - 052 005 - 053 005

, ,

() . "" : " " . : ()

Cracking . . . : . .

,9000C . :2CH3)CH2)10CH3 CH3(CH2)8CH3 + CH2=CH

, , . : .

() - , 4500C .5500C :61CH3)CH2)12CH3 CH3(CH2)4CH=CH2 + C7H : . " " , . .

: ( ):X-Y X + Y

, , :X-Y -:X+ + Y

: C-C ( C-H )

C-C: C-C .D 3CH3CH2CH2CH

122 CH3CH

D

23CH3CH2CH2 + CH

3CH3CH2CH2CH

CH3CH2CH2CH3

D

I CH3CH2

II

III

+ CH3CH2CH2 + CH3

: CH3CH2CH2CH2CH2CH3

II +II I +II

CH3CH2CH2CH2CH3CH3CH2CH3 CH3CH3

I +III III +III

( H- C ): C-H . R 13R + CH3CH2CH2CH + R 2RH + CH3CH2CH2CH

23CH3CH2CH2CH + RH 3CH3CH2CHCH

, . .

( ).2R + CH3CH2CH + RH

] 2[CH3CHCH

2CH3CH=CH

.

() ) - (Combustion . - , ( ).: .)2C4H10 (g) + 13O2 (g) 8CO2 (g) + 10H2O (g H = -2879kJ/mol

() , . : ().

: - .)2CH4 (g) + 3O2 (g) 2CO (g) + 4H2O (g )CH4 (g) + O2 (g) C (s) + 2H2O (g

4

()

Substitution Reaction : A-B + C-D A-C + B-D

, . :H C H H H Methane + Cl-Cl Light H C H H Cl Chloromethane + H-Cl

CnH2n+2 + X2 CnH2n+1X + HXhn H3C-CH3 + Cl2 H3C-CH2Cl + HCl (1) . hn X=Cl, Br, I

(2) .(3) , . : 4CH 2Cl hn 4CH3Cl + CH2Cl2 + CHCl3 + CCl

: . . : () (, ) ()

hn X2 2 X

() ()

CnH2n+2 + X HX + CnH2n+1 CnH2n+1 + X2 CnH2n+1X + X

() : 1.

+ R + R

R

R-R RH + R-CH=CH-R

2. .

R-CH2-CH-R

: - ( ).

, . : . ?2CH3CH2CH2CH3 Cl CH3CH2CH2CH2 Cl Light and 3CH3CHCH2CH Cl

%06 %04

() .

, .2CH3CH2CH2CH3 Cl CH3CH2CH2CH2 Cl Light and 3CH3CHCH2CH Cl

%54

%55

.

2H3C < H3C-CH2-CH 01

3< H3C-CH-CH 02

< (H3C)3C 03

, , .

:2Cl2 > Br . 2 I ( ). 2 F ( ). , .

2CH3CH2CH3 Cl CH3CH2CH2 Cl Light and 3CH3CHCH Cl

%04

%06

: .

3CH3CH2CH

2Br CH3CH2CH2 Br Light and 3CH3CHCH Br

%3 %79

?

>=

1) ) : -2 () -2,4 -2,2,3 ) ? ) , ?

2) .

CnH2n

cyclopropane cyclobutane

cyclopentane cyclohexane

cycloheptane

cyclooctane

06

09

801

:

901

03

) Strain energy (kcal mol

3

1-

4

52 02 51 01 5 0 2 4 6

9 7 5 68 01 21

41 21

61

41

61

81

n

, "" ).(cyclo , , .

CH3

CH3

1,3-Dimethylcyclohexane

: () , . : .

5

- - . / : ( - 1) ( - 2)

Alkenes CnH2n

C

C

( ) ( .) ) (Olefines .

Alkenes C2H4 C3H6 C4H8 C5H10 C6H12 ethene (ethylene) propene (propylene) butene (butylene) pentene hexene

, .ene , . . .

H C H C

H H

CH2=CH2

H C H C

CH3 H

CH3CH=CH2

? CH2=CHCH2CH3 1-butene

CH3CH=CHCH3

2-butene

: . , .: 8?C4H 01?C5H

? 2-butene

H

CH3

CH3 C H C

CH3 H

C C H CH3 trans-2-butenem.p. -1050C b.p. 10C

cis-2-butenem.p. -1390C b.p. 3.70C

. . . , .

3-heptene :1 CH3CH2CH=CHCH2CH2CH3

CH3CH2 C C H

H CH2CH2CH3

CH3CH2 C C H

CH2CH2CH3 H

trans-3-heptene

cis-3-heptene

4-ethyl-3-heptene :2 CH3CH2CH=CCH2CH2CH3 CH2CH3

CH3CH2

CH2CH3

CH3CH2

CH2CH2CH3

CH

CCH2CH2CH3

CH

CCH2CH3

trans-4-ethyl-3-heptene

cis-4-ethyl-3-heptene

3-ethyl-3-hexene :3 CH3CH2CH=CCH2CH3 CH2CH3

CH3CH2

CH2CH3

CH

CCH2CH3

.3

.: RCH=CHR RCH=CHR RRC=CRR

. . . . 4 . - 5 81 . - 91 . .

: )(additionC C + X-Y C C X Y

, , .

2 Cl 2Br

C

C

+ Cl-Cl

C C Cl Cl

CH3CH CHCH3 + Cl2 CH3CH CH CH3 Cl Cl2-butene 2,3-dichlorobutane