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III Õèìè÷åñêèå ñâîéñòâà

Ïðî÷èòàéòå:
  1. AT : õèìè÷. Ïðèðîäà, ñòðîåíèå, ñâîéñòâà, ìåõàíèçì ñïåöèôè÷åñêîãî âçàèìîäåéñòâèÿ ñ ÀÃ
  2. I. Îáùèå ñâîéñòâà êîðêîâûõ ýíäîêðèíîöèòîâ
  3. I. Ðàçìåðû è òèíêòîðèàëüíûå ñâîéñòâà âîëîêîí
  4. II. Ôèçè÷åñêèå è ôèçèêî-õèìè÷åñêèå ìåòîäû
  5. IV.ÁÈÎÕÈÌÈ×ÅÑÊÈÅ ÑÂ-ÂÀ
  6. IV.ÁÈÎÕÈÌÈ×ÅÑÊÈÅ ÑÂ-ÂÀ
  7. À. Ñâîéñòâà è âèäû ðåöåïòîðîâ. Âçàèìîäåéñòâèå ðåöåïòîðîâ ñ ôåðìåíòàìè è èîííûìè êàíàëàìè
  8. ÀÄÀÏÒÈÂÍÛÅ ÑÂÎÉÑÒÂÀ ÞÍÎÇÈÌÎÂ
  9. Àíòèãåííûå ñâîéñòâà

 

 

1. Ðåàêöèè íóêëåîôèëüíîãî ïðèñîåäèíåíèÿ:

 

Ìåõàíèçì ðåàêöèè

 

 

H H δ-O H O H

\ δ+ δ- - \ δ+ / \ / +H2O |

C = O + Z: C Ñ H – C – OH

/ / δ- / \ |

H H Z H Z Z

 

1) ðåàêöèè ñ ñèíèëüíîé êèñëîòîé:

 

O OH

| Í+ β α|

CH3 – C = O + HCN CH3 – CH – CN CH3 – CH – CN

| (öèàíãèäðèíû)

H íèòðèë-α-ãèäðîêñè

ïðîïèîíîâîé êèñëîòû

 

2) ðåàêöèè ñ ãèäðîñóëüôèòîì íàòðèÿ:

O OH

+ - | | +Na +

CH3 – C = O + Na(HSO3) CH3 – CH – SO3H CH3 – CH – SO3

|

H â ýòó ðåàêöèþ âñòóïàþò íå âñå êåòîíû: òîëüêî òå, êîòîðûå èìåþò

ãðóïïó –ÑÍ3 èëè àëèôàòè÷åñêèé öèêë õîòÿ áû ñ îäíîé ñòîðîíû

îò êàðáîíèëüíîé ãðóïïû

OH

2 1 |

CH3 – CH – SO3Na

(ãèäðîêñèñóëüôîíàòû)

1 – ãèäðîêñèýòàíñóëüôîíàò íàòðèÿ – 1

 

 

3) ðåàêöèè ñî ñïèðòîì (òîëüêî äëÿ àëüäåãèäîâ):

 

O

δ+ δ– | +H+ +H+

CH3 – C = O + CH3OH CH3 – CH CH3 – CH – OH

| | |

H OCH3 OCH3

1-ìåòîêñèýòàíîë-1

 

 

H – O+ – H H – O+ – CH3

| - H2O + +CH3OH |

CH3 – CH CH3 – CH CH3 – CH

| | | - Í+

OCH3 OCH3 O – CH3

 

 

O – CH3

|

CH3 – CH

|

O – CH3

(àöåòàëè)

1, 1 – äèìåòîêñèýòàí

 

4) ðåàêöèè ñ ðåàêòèâîì Ãðèíüÿðà:

 

OMgCl OH

δ+ δ- δ- δ+ | + Í2Î |

CH3 – C = O + CH3MgCl CH3 – CH CH3 – CH – CH3

| |

H CH3

 

 

5) ðåàêöèè ñ àììèàêîì:

 

 

ðåàêöèè ñ àììèàêîì ó àëüäåãèäîâ è êåòîíîâ èäóò ïî ðàçíîìó

 

à) àëüäåãèäû

 

OOH

| |

CH3 – C = O + NH3 CH3 – CH CH3 – CH

| | | - H2O

H NH3+ NH2

 

CH3 – CH = NH

 

èìèíû, ýòàíàëüäèìèí, àöåòàëüäèìèí(NH – èìèíî ãðóïïà)

 

 

á) êåòîíû

 

 

CH3

|

α + CH3 – C = O

CH3 – C = O + C2H5O CH2 – C = O

| -Ñ2H5OH |

CH3 CH3

 

OOH O

| +Í2Î | ||

CH3 – C – CH2 – C = O CH3 – C – CH2 – C – CH3

| | |

CH3 CH3 CH3

 

 

CH3 O NH2 O

| || +NH3 5 4| 3 2|| 1

CH3 – C = CH – C – CH3 CH3 – C – CH2 – C – CH3

|

CH3

 

4–àìèíî–4–ìåòèëïåíòàíîí–2

 

 

6) ðåàêöèè ñ ïðîèçâîäíûìè àììèàêà:

 

O OH

| | - H2O

CH3–C=O + NH2–OH CH3–CH CH3–CH CH3–CH=N–OH

| ãèäðîêñèëàìèí +| | (îêñèìû)

H NH2 – OH NH – OH ýòàíàëüäîêñèì

 

+CH3–CÍ=O

CH3–C=O + NH2–NH2 CH3–CH=N–NH2 CH3–CH=N–N=CH–CH3

| ãèäðàçèí ýòàíàëüãèäðàçîí àçèíû

Í (ýòàíàëüäàçèí)

 

CH3 – C = O + NH2 – NH – C6H5 CH3 – CH = N – NH

| ôåíèëãèäðàçèí |

H

 

ýòàíàëüôåíèëãèäðàçîí

2. Ðåàêöèè êîíäåíñàöèè:

 

1) àëüäîëüíàÿ êîíäåíñàöèÿ:

 

-

(C 2H5O) Na

CH3 – C = O CH2 – C = O

| - C 2H 5OH |

H – Na + H

 

O OH

| +H2O |

CH3 – C = O + CH2 – C = O CH3 – CH – CH2 – C = O CH3 – CH – CH2 – C = O

| | | |

H H H H

 

(àëüäîëü)

3 – ãèäðîêñèáóòàëü

2) êðîòîíîâàÿ êîíäåíñàöèÿ:

 

 

OH

| t

CH3 – CH – CH2 – C = O CH3 – CH = CH – C = O

| –H2O |

H H

êðîòîíîâûé àëüäåãèä

áóòåí – 2 – àëü

 

 

3) êîíäåíñàöèÿ Êàííèööàðî (òîëüêî äëÿ àëüäåãèäîâ):

 ðåàêöèþ âñòóïàþò òîëüêî òå àëüäåãèäû, ó êîòîðûõ íåò àòîìà Í â α – ïîëîæåíèè

 

NaOH

H – C = O H – C = O + CH3OH

| 50% |

H ONa

 

- C = O NaOH - CH2

| + H – C =O | + H – C = O

H | 50% OH |

H ONa

áåíçèëîâûé ôîðìèàò íàòðèÿ

ñïèðò

 

 

CH3 CH3

| |

CH3 – C – C = O + H – C = O CH3 – C – CH2 + H – C = O

| | | | | |

CH3 H H CH3 OH ONa

 

 

4) êîíäåíñàöèÿ Òèùåíêî (òîëüêî äëÿ àëüäåãèäîâ):

 

(C2H5O) 3Al

CH3 – C = O + CH3 – C = O CH3 – C = O

| | |

H H O – CH2 – CH3

 

ýòèëàöåòàò (ýòèëîâûé ýôèð óêñóñíîé êèñëîòû)

 

 

5) êîíäåíñàöèÿ Êëÿéçåíà:

 

 

OH

|

- Ñ = O +C2H5ONa - CH – CH2 – C = O t CH = CH – C = O

| + CH3 – C = O | - H2O |

H | H H

H

êîðè÷íûé

àëüäåãèä

 

6) êîíäåíñàöèÿ Ïåðêèíà:

O

C2H5ONa |

CH3 – C = O + CH3 – C = O CH3 – CH – CH2 – C = O

| | | –H2O

H O – C = O O – C = O

| |

CH3 CH3

àíãèäðèä óêñóñíîé êèñëîòû

 

OH

| t

CH3 – CH – CH2 – C = O CH3 – CH = CH – C = O + CH3 – C = O

| -H2O | |

O – C = O OH OH

êðîòîíîâàÿ êèñëîòà óêñóñíàÿ

êèñëîòà

2. Ðåàêöèè îêèñëåíèÿ:

 

1) îêèñëåíèå àëüäåãèäîâ

 

à) ðåàêöèÿ ñåðåáðÿíîãî çåðêàëà

 

OH

|

CH3 – CH = O + Ag2O CH3 – C = O + 2Ag

 

ONH4

|

CH3 – CH = O +2[ Ag(NH3)2]OH CH3 – C = O + 2Ag + 3NH3 + H2O

 
 

 


á) ðåàêöèÿ ñ ôåëèíãîâîé æèäêîñòüþ

 

O O

|| ||

C – ONa C – ONa

| |

CHOH + Cu(OH)2 + CH3 – C = O CHOH + Cu2O + CH3 – C = O

| | | |

CHOH H CHOH OH

| |

C – OÊ C – OÊ

|| ||

O O

ñîëü âèííîé êèñëîòû

 

 

â) ðåàêöèÿ ñ ôóêñèíñåðíèñòîé êèñëîòîé:

 

 


+

 

 

Í – ÑÍ = Î

 

2) îêèñëåíèå êåòîíîâ:

 

[O]

CH3 – C – CH3 H – C = O + CH3 – C = O

|| | |

O OH OH

 

 

I

CH3 – C = O + CH3 – CH2 – CH – C = O

[O] | | |

CH3–CH2–C–CH–CH2–CH3 OH CH3 OH

|| | II

O CH3 CH3 – CH2 – C = O + CH3 – CH2 – C – CH3

| ||

OH O

 

 

Ïðàâèëî Ïîïîâà – ðàñùåïëåíèå ïðîèñõîäèò â áîëüøåé ñòåïåíè ïðè íàèìåíåå ãèäðîãåíèçèðîâàííîì óãëåðîäíîì àòîìå

 

3. Ðåàêöèè âîññòàíîâëåíèÿ:

 

[H]

CH3 – C – CH3 CH3 – CH – CH3

|| |

O OH

[H]

CH3 – C = O CH3 – CH2 – OH

|

H

 

5. Ðåàêöèè ïîëèìåðèçàöèè (òîëüêî äëÿ àëüäåãèäîâ):

 

 

n H – C = O [ – CH2 – O – ]n

|

H ïàðàôîðìàëüäåãèä (ïîëèôîðìàëüäåãèä)

 

Ìîãóò îáðàçîâàòüñÿ öèêëè÷åñêèå ñîåäèíåíèÿ

O CH2 – O

/ \ / \

3 H – C = O CH2 CH2 O CH2

| | | èëè | |

H O O CH2 O

\ / \ /

CH2 O – CH2

òðèîêñèìåòèëåí òåòðàîêñèìåòèëåí

 

6. Ðåàêöèÿ çàìåùåíèÿ:

 

Cl O

α ð | ||

CH3 – CH2 – C = O + Cl2 CH3 – CH – CÍ + HCl

|

H

 

 

O Cl

|| |

CH3 – C + PCl5 CH3 – CH + POCl3

| |

H Cl

 

 

Cl

|

CH3 – C – CH3 + PCl5 CH3 – C – CH3 + POCl3

|| |

O Cl

 


Äàòà äîáàâëåíèÿ: 2015-09-03 | Ïðîñìîòðû: 1179 | Íàðóøåíèå àâòîðñêèõ ïðàâ



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