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?AOA?AO

Ii i?aaeiaoo: Oeiey

Ia oaio: Aetheica

Noaiaithe Aeieo?ee

10 “A” eeann oeieu ?1910

Iineaa 1997 aiae

Ieai.

1. Iauea naaaeaiey (3 no?aieoea)

a) D-aetheica

— (-D-aetheica

— (-D-aetheica

a) L-aetheica

3. Iaoiaeaeaiea a i?e?iaea (4 no?aieoea)

4. Iieo/aiea (5 no?aieoea)

5. I?eiaiaiea (5 no?aieoea)

6. Oece/aneea naienoaa (6 no?aieoea)

7. Oeie/aneea naienoaa (6 no?aieoea)

8. ?eaica e aeaciene?eaica (7 no?aieoea)

9. Iaeioi?ua eioa?aniua oaeou (8 no?aieoea)

10. Eeoa?aoo?a (10 no?aieoea)

Oi?ioea aetheicu C6H12O6.

Aetheica — iiiinaoa?eae, iaeia ec ainueie eciia?iuo aeueaeiaaenic.
Iiey?iay ianna 180 a/iieue. Aetheica a aeaea D-oi?iu (aeaenoica,
aeiia?aaeiue naoa?) yaeyaony naiui ?ani?ino?ai?iiui oaeaaiaeii.
D-aetheica (iau/ii a? iacuaatho i?inoi aetheicie) ano?a/aaony a
naiaiaeiii aeaea e a aeaea ieeainaoa?eaeia (o?inoieeiaue naoa?, iiei/iue
naoa?), iieenaoa?eaeia (e?aoiae, aeeeiaai, oeaeetheica, aeaeno?ai),
aeeeiceaeia e ae?oaeo i?iecaiaeiuo. A naiaiaeiii aeaea D-aetheica
niaea?aeeony a ieiaeao, oeaaoao e ae?oaeo i?aaiao ?anoaiee, a oaeaea a
aeeaioiuo oeaiyo (a e?iae, iicao e ae?.). D-aetheica yaeyaony aaaeiaeoei
enoi/ieeii yia?aee a i?aaieciao aeeaioiuo e iee?ii?aaieciia. Eae e
ae?oaea iiiinaoa?eaeu D-aetheica ia?acoao ianeieueei oi?i.
E?enoaeee/aneay D-aetheica iieo/aia a 2-o oi?iao: (-D-aetheica (?enoiie
1) e (-D-aetheica (?enoiie 2).

?enoiie 1 ((-D-aetheiie?aiica) ?enoiie 2
((-D-aetheiie?aiica)

(-D-aetheica

tie 146(N [(]D= + 112,2( (a aiaea), e?enoaeeece?oaony ec aiaeu a
aeaea iiiiaeae?aoa n tie 83(N.

(-D-aetheica

Iieo/atho e?enoaeeecaoeeae D-aetheicu ec ie?eaeeia e iaeioi?uo
ae?oaeo ?anoai?ia. tie 148-150(N, [(]D= + 18,9( (a aiaea).

A aiaeiii ?anoai?a onoaiaaeeaaaony ?aaiiaanea iaaeaeo ianeieueeeie
acaeiii?aa?auathueieny oi?iaie D-aetheicu: (- e (-ie?aiiciuie , (- e
(-oo?aiiciuie, ioe?uoie aeueaeaaeaeiie

(?enoiie 3) e aeae?aoiie oi?iie. A ?aaiiaaniie nenoaia a aiaea [(]D= +
52,7(.

CHO

(

HCOH

(

HOCH

(

HCOH

(

HCOH

(

CH2OH

?enoiie 3 (aeueaeaaeaei-D-aetheica)

L-aetheica

L-aetheica iieo/aia neioaoe/anee, ainnoaiiaeaieai eaeoiia L-aetheiiiaie
eeneiou. (-L-aetheica — e?enoaeeu tie 142-143(N [(]D= – 95,5( (a aiaea)
e – 51,4( (?aaiiaaniay nenoaia a aiaea). Oeie/aneea naienoaa L-aetheicu
oaeea aea, eae o D-aetheicu.

Iaoiaeaeaiea a i?e?iaea

A iniaii aeaea aetheica niaea?aeeony ii/oe ai anao i?aaiao cae?iuo
?anoaiee. Iniaaiii a? iiiai a aeiia?aaeiii niea, iiyoiio aetheico
eiiaaea iacuaatho aeiia?aaeiui naoa?ii. I?ae a iniiaiii ninoieo ec niane
aetheicu n o?oeoicie.

A i?aaiecia /aeiaaea aetheica niaea?aeeony a iuooeao, a e?iae (0.1 –
0.12 %) e neoaeeo iniiaiui enoi/ieeii yia?aee aeey eeaoie e oeaiae
i?aaiecia. Iiauoaiea eiioeaio?aoeee aetheicu a e?iae i?eaiaeeo e
oneeaieth au?aaioee ai?iiia iiaeaeaeoaei/iie aeaeacu — einoeeia,
oiaiueoathuaai niaea?aeaiea yoiai oaeaaiaea a e?iae. Oeie/aneay yia?aey
ieoaoaeueiuo aauanoa, iinooiathueo a i?aaieci, caeeth/aia a eiaaeaioiuo
naycyo iaaeaeo aoiiaie. A aetheica eiee/anoai iioaioeeaeueiie yia?aee
ninoaaeyao 2800 eAeae ia 1 iieue (oi anoue ia 180 a?aii).

Iieo/aiea

Ia?aue neioac aetheicu ec oi?iaeueaeaaeaea a i?enoonoaee aeae?ieneaea
eaeueoeey aue i?iecaaae?i A. I. Aooea?iaui a 1861 aiaeo:

O

(( Ca(OH)2

6H—C ((( C6H12O6

\\

H

Aetheica iiaeao auoue iieo/aia aeae?ieecii i?e?iaeiuo aauanoa, a ninoaa
eioi?uo iia aoiaeeo. A i?iecaiaenoaa a? iieo/atho aeae?ieecii
ea?oioaeueiiai e eoeo?ociiai e?aoiaea eeneioaie.

H2SO4, t

(C6H10O5)n + nH2O ((( nC6H12O6

Iieiua neioacu aetheicu, inouanoae?iiua, enoiaey ec aeea?iia e?ieaeia,
a oaeaea ec aeeoea?eiiaiai aeueaeaaeaea e aeeieneaoeaoiia, eiatho eeoue
oai?aoe/aneee eioa?an.

A i?e?iaea aetheica ia?yaeo n ae?oaeie oaeaaiaeaie ia?acoaony a
?acoeueoaoa ?aaeoeee oioineioaca:

oei?ioeee

6CO2 + 6H2O (((( C6H12O6 + 6O2 – Q

A i?ioeanna yoie ?aaeoeee aeeoioee?oaony yia?aey Nieioea.

I?eiaiaiea

Aetheica yaeyaony oeaiiui ieoaoaeueiui i?iaeoeoii. A i?aaiecia iia
iiaeaa?aaaony neiaeiui aeioeie/aneei i?aa?auaieyi a ?acoeueoaoa eioi?uo
ia?acoaony aeeieneae oaea?iaea e aiaea, i?e yoi auaeaeyaony yia?aey
niaeanii eoiaiaiio o?aaiaieth:

C6H12O6 + 6O2 (( 6H2O + 6CO2 + 2800 eAeae

Yoio i?ioeann i?ioaeaao nooiai/aoi, e iiyoiio yia?aey auaeaeyaony
iaaeeaiii.

Aetheica oaeaea o/anoaoao ai aoi?ii yoaia yia?aaoe/aneiai iaiaia
aeeaioiie eeaoee (?anuaieaiea aetheicu). Noiia?iia o?aaiaiea auaeyaeeo
oae:

C6H12O6 + 2H3PO4 + 2AAeO (( 2C3H6O3 + 2AOO + 2H2O

Oae eae aetheica eaaei onaaeaaaony i?aaieciii, a? eniieuecotho a
iaaeeoeeia a ea/anoaa oe?aieythuaai ea/aaiiai n?aaenoaa i?e yaeaieyo
na?aea/iie neaainoe, oiea , iia aoiaeeo a ninoaa e?iaicaiaiythueo e
i?ioeaioieiauo aeeaeeinoae. Oe?iei i?eiaiytho aetheico a eiiaeeoa?neii
aeaea (ecaioiaeaiea ia?iaeaaea, ea?aiaee, i?yieeia e o. ae.), a
oaenoeeueiie i?iiuoeaiiinoe a ea/anoaa ainnoaiiaeoaey, a ea/anoaa
enoiaeiiai i?iaeoeoa i?e i?iecaiaenoaa anei?aeiiauo e aeeeiiiauo eeneio,
aeey neioaca ?yaea i?iecaiaeiuo naoa?ia e o.ae.

Aieueoia cia/aiea eiatho i?ioeannu a?iaeaiey aetheicu. Oae, iai?eia?,
i?e eaaoaiee eaionou, iao?oeia, iieiea i?ienoiaeeo iiei/iieeneia
a?iaeaiea aetheicu, oae aea eae e i?e neeiniaaiee ei?iia. Anee
iiaeaa?aaaiay neeiniaaieth ianna iaaeinoaoi/ii oieioiaia, oi iiae
aeeyieai i?iieeoaai aicaeooa i?ienoiaeeo ianeyiieeneia a?iaeaiea e ei?i
noaiiaeony iai?eaiaeai e i?eiaiaieth.

Ia i?aeoeea eniieuecoaony oaeaea nie?oiaia a?iaeaiea aetheicu, iai?eia?
i?e i?iecaiaenoaa ieaa.

Oece/aneea naienoaa

Aetheica — aanoeaaoiia e?enoaeee/aneia aauanoai ni neaaeeei aeonii,
oi?ioi ?anoai?eiia a aiaea. Ec aiaeiiai ?anoai?a iia auaeaeyaony a aeaea
e?enoaeeiaeae?aoa C6H12O6 ( H2O. Ii n?aaiaieth ni naaeeiae/iui naoa?ii
iia iaiaa neaaeeay.

Oeie/aneea naienoaa

Aetheica iaeaaeaao oeie/aneeie naienoaaie, oa?aeoa?iuie aeey nie?oia e
aeueaeaaeaeia. E?iia oiai, iia iaeaaeaao e iaeioi?uie niaoeeoe/aneeie
naienoaaie:

Naienoaa, iaoneiaeaiiua iaee/eai a iieaeoea Niaoeeoe/aneea naienoaa

aeae?ieneeueiuo a?oii aeueaeaaeaeiie a?oiiu

1. ?aaae?oao n ea?aiiiauie eeneioaie n ia?aciaaieai neiaeiuo yoe?ia
(iyoue aeae?ieneeueiuo a?oii aetheicu anooiatho a ?aaeoeeth n eeneioaie)
1. ?aaae?oao n ieneaeii na?aa?a (I) a aiiea/iii ?anoai?a (?aaeoeey
“na?aa?yiiai ca?eaea”):

CH2OH(CHOH)4-COH + Ag2O( CH2OH(CHOH)4-CO2H + 2Ag( Aetheica niiniaia
iiaeaa?aaoueny a?iaeaieth: a) nie?oiaia a?iaeaiea

C6H12O6(2CH3-CH2OH+ CO2(

a) iiei/iieeneia a?iaeaiea

C6H12O6(2CH3-CHOH-COOH

iiei/iay eeneioa

2. Eae iiiaiaoiiiue nie?o ?aaae?oao n aeae?ieneaeii iaaee (II) c
ia?aciaaieai aeeiaieyoa iaaee (II) 2.Ieeneyaony aeae?ieneaeii iaaee (II)
(n auiaaeaieai e?aniiai inaaeea)

3. Iiae aeaenoaeai ainnoaiiaeoaeae i?aa?auaaony a oanoeaoiiiue nie?o a)
ianeyiieeneia a?iaeaiea

C6H12O6(C3H7COOH + 2H2( + 2CO2(

ianeyiay eeneioa

D-aetheica aea?o iauea ?aaeoeee ia aeueaeicu, iia yaeyaony
ainnoaiaaeeaathuei naoa?ii, ia?acoao ?yae i?iecaiaeiuo ca n/?o
aeueaeaaeaeiie a?oiiu (oaieeaeae?acii, n-a?iioaieeaeae?acii e ae?.).
Icacii aetheicu eaeaioe/ai icaiiio iaiiicu, eioi?ay yaeyaony yieia?ii
aetheicu, e icaciio o?oeoicu. I?e ainnoaiiaeaiee aetheicu ia?acoaony
oanoeaoiiiue nie?o ni?aeo; i?e ieeneaiee aeueaeaaeaeiie a?oiiu aetheicu
— iaeiiiniiaiay D-aetheiiiaay eeneioa, i?e aeaeueiaeoai ieeneaiee —
aeaooiniiaiay D-naoa?iay eeneioa. I?e ieeneaiee oieueei aoi?e/iie
nie?oiaie a?oiiu aetheicu (i?e oneiaee caueou aeueaeaaeaeiie a?oiiu)
ia?acoaony D-aetheo?iiiaay eeneioa. Ia?aciaaiea D-aetheo?iiiaie eeneiou
ec D-aetheicu iiaeao i?ienoiaeeoue i?e aeaenoaee oa?iaioia ieneaeac eee
aeaaeae?iaaiac aetheicu. I?e ie?ieeca D-aetheicu ia?acothony aeeeicaiu:
(-aeeeicai e eaaiaetheicai ((-aetheicai).

Aeey eiee/anoaaiiiai ii?aaeaeaiey aetheicu i?eiaiythony
eaei?eiao?e/aneea, eiaeiiao?e/aneea e ae?oaea iaoiaeu.

?eaica e aeaciene?eaica

Ec iaioic aieueoie eioa?an i?aaenoaaeytho ?eaica e aeaciene?eaica, eai
iie aoiaeyo a ninoaa ioeeaeiiauo eeneio. No?oeoo?iua oi?ioeu ?eaicu e
aeaciene?eaicu n ioe?uoie oeaiueth neaaeothuea:

H H H H O H H H H O

( ( ( ( // ( ( ( (
//

H ( C ( C ( C ( C ( C H ( C ( C ( C ( C ( C

( ( ( ( \ ( ( ( (
\

OH OH OH OH H OH OH OH H H

?eaica
aeaciene?eaica

Iaeioi?ua eioa?aniua oaeou

Iaeioi?ua eyaooee iaoee i?eiaiaiea aetheica a nai?i i?aaiecia —
ethaiiuoiia, oioy e ai?acaei iaiaa aaaeiia. A ceiiea a?aiy eiiaaea
iiaeii iaeoe eyaooae, ai??coeo a eaaeyiua aeuau, ii iinea iooaeaaiey
caiiiaiaeiua iaeeaatho. Eae aea iie ooeo?ythony ia cai??ciooue
iania?oue? Ieacuaaaony, n ianooieaieai oieiaeia a e?iae eyaooee a 60 ?ac
oaaee/eaaaony eiee/anoai aetheicu. Yoi iaoaao ia?aciaaieth aioo?e
i?aaiecia e?enoaeeeeia eueaea.

Aeeeieec

Aa?ie ?iiaia AEthey Aa?ia “Aeaoe eaieoaia A?aioa” oieueei niae?aeenue
iioaeeiaoue iynii iiaeno?aeaiiie eie aeeeie eaiu (aoaiaei), eae aae?oa
auynieeinue, /oi iii niaa?oaiii ia nuaaeiaii.

“Auoue iiaeao, iii neeoeii aeieai eaaeaei?” – icaaea/aiii ni?inee iaeei
ec ieo.

“Iao, iii, e niaeaeaieth, neeoeii aeieai aaaeaei! – ioaaoee
o/?iue-aaia?ao Iaaaiaeue – Iyni aoaiaei aeonii oieueei oiaaea, eiaaea
aeeaioiia oaeoi ai a?aiy ioaeuoa, ii anee ca iei aeieai ioioeoueny e
aeeaioiia aeieai aaaeaei, oiaaea aai iyni ianuaaeiaii.”

A?yae ee Iaaaiaeue noiae au iauynieoue i?e/eio iienaiiiai ei yaeaiey.
Ii, iieuecoynue aeaiiuie nia?aiaiiie iaoee, naeaeaoue yoi nianai
iao?oaeii. Ia/aoue i?eae?ony, i?aaaea, ianeieueei ecaeaeaea.

Eiaaea eeaoea aeuoeo eenei?iaeii, aetheica “nai?aao” a iae,
i?aa?auaynue a aiaeo e oaeaeeneue aac, e auaeaeyao yia?aeth. Ii,
i?aaeiieiaeei, aeeaioiia aeieai aaaeeo, eee /aeiaae auno?i auiieiyao
eaeoth-oi oyae?eoth oece/aneoth ?aaioo, iai?eia?, eieao ae?iaa.
Eenei?iae ia oniaaaao iiianoue a eeaoee iuooe. Oai ia iaiaa eeaoee
“caaeuoathony” ia n?aco. Ia/eiaaony ethaiiuoiue i?ioeann — aeeeieec (/oi
a ia?aaiaea icia/aao “?anuaieaiea naoa?a”). I?e ?aniaaea aetheicu
ia?acoaony ia aiaea e oaeaeeneioa, a aieaa neiaeiia aauanoai — iiei/iay
eeneioa. Eaaeaeue, eoi i?iaiaae eeneia iieiei eee eaoe?, ciaeii n a?
aeonii.

Yia?aee i?e aeeeieeca auaeaeyaony a 13 ?ac iaiueoa, /ai i?e aeuoaiee.
*ai aieueoa iiei/iie eeneiou iaeiieeinue a iuooeao, oai neeueiaa /aeiaae
eee aeeaioiia /oanoaoao eo onoaeinoue. Iaeiiaoe, ana caianu aetheicu a
iuooeao enoiuathony. Iaiaoiaeei ioaeuo. Iiyoiio, ia?anoaa eieioue ae?iaa
eee acaaaeaa ii aeeeiiie eanoieoea, /aeiaae iau/ii “ia?aaiaeeo aeoo”,
ainiieiyy iaaeinoaoie eenei?iaea a e?iae. Eiaiii iiei/iay eeneioa
naeaeaea iaaeoniui iyni aeeaioiiai, iiaeno?aeaiiiai aa?iyie AEthey
Aa?ia.

Eeoa?aoo?a

E?aoeay oeie/aneay yioeeeeiiaaeey

O/aaiee Oeiey 10 eeann

Yioeeeeiiaaeey aeey aeaoae — Aeieiaee

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