פתרון חוברת תרגילים בכימיה אורגנית ופולימרים

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פתרונות לחוברת תרגילים מלאה לקורס כימיה אורגנית וםולימרים

Text of פתרון חוברת תרגילים בכימיה אורגנית ופולימרים

0 1. . , . . / . 3CH3CH2CH2CH2CH . 21C5H . 3CH3CH2C(CH3)2CH

. 41C6H

.

CH3CH2CH(CH2CH3)CH2CHClCH2BrCl

. C8H16ClBr

Br

.

2)3(CH3CH2 )2C = C(CH2CH

. 02C10H

.

2. / :

III 42C11H 23C15H 21C6H

II 3CH3CH2CH(CH3)CH2C(CH3)2CH2CH2CH

I

I II III

3CH3CH2CH(CH3)CH2CH2C(CH2CH3)2CH2CH2CH2CH 2)3H2C=C(CH2CH

3. , / / . ?

3CH CH H2C H2C CH CH H3C 3CH CH CH

H H2C H2C C 2CH 3CH H C C 3CH 3CH 3CH

, - : . . 4. B , A C ?

.A 5. / : )( CH3CH2OH CH3COOH 1. 2. 3.

3CH3CH2OCH2CHO

3CH3CCH O

4.

O

CH3CH2CH

5.

3CH3 C OCH2CH

6.

6. ?

1. 7. ? 3CH3COCH 1 CH3CH2CH2O 2 CH3CH2COOH 3 CH3CH2CHO 4 1.

8. :

/ / . / / . / )01(, )02(, )03(, )04(.01 02 02 02 02

3CH C03 04

H OH02 02

2CH

2CH 01 03 3CH04

C02

2CH 2CH

2CH02 02

CH

2CH C

C C03 02

CH02

03

CH

2CH

O

CH

2CH

1 , 1. 21C5H

2. 41C6H

3. / IUPAC : (

4-ethyl-2,6-dimethyloctane (

5-ethyl-2,3,3-trimethylheptane (

4-ethyl-5-methyloctane

( 3CH3(CH2)8CH n-decane ( 3)3(CH3)2CHCH2CH2C(CH 2,2,5-trimethylhexane 4. :

8 , octane 4-ethyl-3,3-dimethyloctane 62C12H 5

( ? / . ( IUPAC . ( / . ( : ) (: ) (: 5

) (: 1 ) (: 1 5. : C3H7Cl ClCH2CH2CH3 1-chloropropane 3CH3CHClCH 2-chloropropane . 2C2H4Br CH3CHBr2 1,1-dibromoethane CH2BrCH2Br 1,2-dibromoethane 6. : . 3-methylpentane . 3-Ethyl-4,7-dimethylnonane .

4-isopropylheptane

.

2,2,4-trimethylhexane

.

7. / : . 3,3-dimethylpentane . n-heptane . 2-methylheptane . n-pentane . 2-methylhexane 2-methylheptane > n-heptane > 2-methylhexane > 3,3-dimethylpentane > n-pentane , . .

2 1( / : 2 C4H10 + 13 O2 8 CO2 + 10 H2O C5H12 + 8 O2 5 CO2 + 6 H2O C7H16 + 11 O2 7 CO2 + 8 H2O 2 C6H14 + 19 O2 12 CO2 + 14 H2O -n 2- -n 3,2-

2( ? ? . 3( / C-C, . : 3CH3CH2CH2CH2 + CH 2CH3CH2CH2 + CH3CH : 3CH3CH2CH2CH2CH2CH2CH2CH 3CH3CH2CH2CH2CH2CH2CH 3CH3CH2CH2CH2CH2CH 3CH3CH2CH2CH 3CH3CH2CH 3CH3CH n-octane n-heptane n-hexane n-butane propane ethane 3CH3CH2CH2CH2CH ,

4( / C-C 2,2- . / , . : 3(CH3)3C + CH : 3CH3C(CH3)2C(CH3)2CH 3CH3CH 2,2,3,3-tetramethylbutane ethane , 2,2- 3CH3C(CH3)2CH :

4(CH3)2C=CH2 + CH

2-methylpropene + methane 2-methylpropene + 2-methylpropane

3(CH3)2C=CH2 + CH3CH(CH3)CH

5 ( ( : : 1- , 2- , 3- 2- )(: 1- -2-, 2- -2-. 4,2-: 1--4,2-, 2--4,2-, 3--4,2-.

-2,2,3 : 1--3,2,2-, 3--3,2,2-, 4--3,2,2- : HCl ( ? 1- )%05( , 2- )%33.33( , 3- )%76.61(. 1- -2- )%09(, 2- -2- )%01(. 1--4,2- )%57(, 2--4,2- )%5.21(, 3--4,2- )%5.21(. 1--3,2,2- )%52.65(, 3--3,2,2- )%52.6(, 4- -3,2,2- )%5.73(. ( , ? : 2- , 3- . : 1- : 2- -2-. : 1- -2- : 3--4,2-. : 1 --4,2- : 3--3,2,2-. : 1--3,2,2-, 4--

3,2,2-. 6( . 1,1-, 2,1-, 2,2-, 3,1-. 7( 2- )( 4 : %1, %5.0, %9, %5.98 / , / " . 1--2- )%1( 01 2--2- )%5.98( 03 2--3- )%9( 02 1--3- )%5.0( 01

8( / . / . Br2 2 Br CH3CH2CH3 + Br HBr + CH3CH2CH2 CH3CH2CH3 + Br HBr + CH3CHCH3 CH3CH2CH2 + Br2 CH3CH2CH2Br + Br CH3CHCH3 + Br2 CH3CHBrCH3 + Br CH3CH2CH2 + CH3CH2CH2 CH3CH2CH2 + CH3CHCH3 CH3CH2CH2 CH2CH2CH3 CH3CH2CH2 CH(CH3)2

CH3CHCH3 + CH3CHCH3 (CH3)2CHCH(CH3)2 CH3CH2CH2 + CH3CH2CH2 CH3CH2CH3 + CH3CH=CH2 CH3CH2CH2 + CH3CHCH3 CH3CH2CH3 + CH3CH=CH2

CH3CHCH3 + CH3CHCH3 CH3CH2CH3 + CH3CH=CH2

/ C6H12 1( / .( ) 21

cyclohexane

methylcyclopentane

1,2-dimethylcyclobutane

1,3-dimethylcyclobutane

1,1-dimethylcyclobutane

ethylcyclobutane

1,2,3-trimethylcyclopropane

1,1,2-trimethylcyclopropane

1-ethyl-2-methylcyclopropane

1-ethyl-1-methylcyclopropane

isopropylcyclopropane

propylcyclopropane

2( / :BrCl

3CH 3CH2CH

3CH

2)3CH(CH

1-bromo-3-methylcycloheptane

1-chloro-3-isopropylcyclooctane

1-ethyl-2-methylcyclopentane

3( ( / -, :3CH 2 + Br

CH2Br

Br

3CH

3CH Br Br

3CH Br

3CH

: HBr ( ? " : 41CH2Br Br 3CH 3CH Br Br 41/3 %34.12 41/1 %41.7 41/4 %85.82 41/4 %85.82 41/2 %92.41 3CH Br 3CH

( , ? /. , , . , , . , , .Br 3CH

CH2Br

3 C5H10 1. / .() H2C CHCH2CH2CH3 1-pentene H2C CCH2CH3 CH3 2-methyl-1-butene H2C CHCHCH3 CH3 3-methyl-1-butene

H H3C

H C C CH2CH3

H H3C

CH2CH3 C C H

CH3CH CCH3 CH3 2-methyl-2-butene

cis-2-pentene

trans-2-pentene

:2. / " Br2 ( :, "Br Br CH2CHCH2CH2CH3 Br Br 1,2-dibromopentane CH2CCH2CH3 CH3 1,2-dibromo-2-methylbutane Br Br CH2CHCHCH3 CH3 1,2-dibromo-3-methylbutane Br Br CH3CHCHCH2CH3 Br Br 2,3-dibromopentane CH3CHCHCH2CH3 Br Br 2,3-dibromopentane CH3CHCCH3 CH3 2,3-dibromo-2-methylbutane

H2 (

CH3CH2CH2CH2CH3 n-pentane

CH3CHCH2CH3 CH3 2-methylbutane

CH3CH2CHCH3 CH3 2-methylbutane

CH3CH2CH2CH2CH3 n-pentane

CH3CH2CH2CH2CH3 n-pentane

CH3CH2CHCH3 CH3 2-methylbutane

.. H2O ( . , CH2CH2CH2CH2CH3 OH 1-pentanol + CH3CHCH2CH2CH3 OH 2-pentanol* CH2CHCH2CH3 OH CH3 2-methyl-1-butanol + OH CH3CCH2CH3 CH3 * 2-methyl-2-butanol CH2CH2CHCH3 OH CH3 3-methyl-1-butanol + OH CH3CHCHCH3 CH3 3-methyl-2-butanol *

OH CH3CHCH2CH2CH3 OH 2-pentanol + CH3CH2CHCH2CH3 OH 3-pentanol CH3CHCH2CH2CH3 OH 2-pentanol + CH3CH2CHCH2CH3 OH 3-pentanol CH3CHCHCH3 CH3 3-methyl-2-butanol + OH CH3CH2CCH3 CH3 * 2-methyl-2-butanol

.. HCl (CH2CH2CH2CH2CH3 Cl 1-chloropentane + CH3CHCH2CH2CH3 Cl 2-chloropentane* CH2CHCH2CH3 Cl CH3 1-chloro-2-methylbutane + Cl CH3CCH2CH3 CH3 2-chloro-2-methylbutane* CH2CH2CHCH3 Cl CH3 1-chloro-3-methylbutane + Cl CH3CHCHCH3 CH3 2-chloro-3-methylbutane*

Cl CH3CHCH2CH2CH3 Cl 2-chloropentane + CH3CH2CHCH2CH3 Cl 3-chloropentane CH3CHCH2CH2CH3 Cl 2-chloropentane + CH3CH2CHCH2CH3 Cl 3-chloropentane CH3CHCHCH3 CH3 2-chloro-3-methylbutane + Cl CH3CH2CCH3 CH3 2-chloro-2-methylbutane*

3. / : ( 4-methyl-2-pentene3CH H H3C H C C 3CHCH 3CH cis-4-methyl-2-pentene trans-4-methyl-2-pentene H H3C 3CHCH C C H

( 3,4-dimethyl-3-hexene3CH 2CH3CH 3CH C C 3CH2CH 3CH 2CH3CH 3CH2CH C C 3CH

cis-3,4-dimethyl-3-hextene

trans-3,4-dimethyl-3-hextene

4. .A ( A . : ,hexene . ( - A . ?A : . 3CH3CH2CH=CHCH2CH 3- A:

5. / 2-butyne : ( ( ( ( )(HBr

CH3C

3CCH

2-butyne 2 1 2-butyne

Cl Cl CH3C CCH3 Cl Cl 2,2,3,3-tetrabromobutan

Cl C CH3 C

CH3 Cl

Cl2

trans-2,3-dichloro-2-butenH CH3 C CH3 C H

H2

CH3CH2CH2CH3 n-butane

trans-2-buteneH CH3 C CH3 C OH

H2O

() Br Br CH3CHCHCH3 2,3-dibromobutaneBr CH3CH2CCH3 Br 2,2-dibromobutaneH C CH3 C Br CH3

HBr

cis-2-bromo-2-butene

. .

:/ trans-2,3-dibromo-2-pentene (Br CH3C CCH2CH3 + B2 r CH3 2-pentyne C C Br CH2CH3

.6

trans-2,3-dibromo-2-penten

1,1,2,2-tetrachloropropane (

Cl Cl CH3C CH + 2 Cl 2 CH3C CH Cl Cl 1,1,2,2-tetrachloropropan

1-propyne

4 , , , , 1. / 2- : 2- 2-bromopropane .

3CH3CHCH OH 2-propanol

+ HBr

3CH3CHCH Br 2-bromopropane

+ H2O

propene

.

3CH3CHCH OH 2-propanol

+H

CH3CH=CH 2 + H2O propene

2. / 2- 2-pentene , .

3CH3CH=CHCH2CH 2-pentene

+ H2O

H

+

3CH3CHCH2CH2CH OH 2-pentanol

+

3CH3CH2CHCH2CH OH 3-pentanol

3. / 2- 2- .3CH3CHCH + NaOH 3CH3CHCH OH 2-propanol + NaBr

Br 2-bromopropane

4. 4- ,4-methylcyclohexene ? / / . : 4- . , . : , , .3CH HO +H 3CH

5. .C5H11OH/ :OH

.I

OH

3HO CH

.II

.III

6. / 5. ?OH OH 3HO CH

][O O O

][O

][O

no reaction

aldehyde

ketone

7. ? .OH ][O O

8. )( ?propanone

O 3CH3CHCH OH 2-propanol ][O 3CH3CCH propanone

9. / .dibutyl ether 32 CH3CH2CH2CH2OH CH3CH2CH2CH2OCH2CH2CH2CH .

O 3CH3COCH2CH

10. /

CH3CH2OH .

: . :][O CH3CH2OH CH3COOH

. :O CH3CH2OH + CH3COOH 3CH3CH2OCCH + HO 2

11. / 2.C5H10O :O 3CH3COCH2CH2CH O CH3CH2CH2CH2COH

O 3HOCH2CH2CCH2CH

O 3CH O CH2CH2CH2CH

12. / / : CH3CH2OH )( CH3COOH . .

3CH3CH2OCH2CH .

O

3CH3CCH

.

O

)(

3CH3COCH2CH

.

O

CH3CH2CH

.

13. / : , 3CH3-O-CH2CH2CH ,CH3CH2CH2OH ,3CH3CH2CH2CH CH3CH2COOH

3CH3CH2COOH > CH3CH2CH2OH > CH3-O-CH2CH2CH3 > CH3CH2CH2CH . . , , -- . . 14. / : , 3CH3CH2CH2CH ,3CH3CH(CH3)CH ,3CH3CH2CH2CH2CH H2O

3H2O > CH3CH2CH2CH2CH3 > CH3CH2CH2CH3 > CH3CH(CH3)CH , . , . , "" . / : , 3CH3-O-CH2CH ,CH3CH2CH2OH ,3CH3CH2CH 15.

CH3CH2COOH