87409

Egzamin 27.06.07

Zadaniel.

O

II

CH3CCH3 +

//° NaOH_a,

H

H,0

G II

-W CH₃Cr>I=CHQh%

A: aceton B: benzaldehyd O    O

C: 4-feny fobut -3*n-2-on (benz>'lidenoaceton)

CHjOCH= CHOR- + CH₃OCH₂GOOC₂H-

O    OH* O

1) CjHrONa (kat.) II    I    II

CH,CCH,CHCH,Ci:H_ł

2)H₃cP. At

A + D: acetylooctan etylu c₂h%OH, -COi E 4-fenyloheptano-26-dion

Mechanizm kondensacji aldolowej

l ⁰

ch₃cch₃

o

o    r o

H    II ©

₃CCH₃ + NaOH 7^—HCH₃C-CH₂-

(P

I

ai,c=ai,

©

Na *H₂0

Qp

OHscl + %bGCH»< __y

H

©0    0    OH O

II H^O I II Pi

ch₃c—ch₂gch₃ CH₃C-CH₂OCH₃ + HCT

QHs    QHs

OH    O

^I    U    J&

C&H-C—CH₂CCH₃ * HCT;

II

°

OHsO

H

całj-

oh ®o 1

I I

QH_sC-at=CX3l_t

H

•qh₅ch=ch—och₃⁺ ho

Zadanie 2.

CH₃    CH₃    CH₃    CH₃    _    CH3

P    I © -H₂0    I©    I    .iP

a) CH_}Cai»OH    CH₃OCH₂OH₂^=as Od₃OCH₂ -    - CH^CCH ,CH, ^== (H^-CHCH,

I    I    I    ©

cn₃    ch₃    ch₃

^b) C&Hs

©

CHjOH

H

jiHs

HjC-y^oH H0^\"^3 Q,H!f    CjHj

(5)-2'fenylobutan>2*ol (R)-2-feny lobut an-2-ol

c) OjHs-Ć^ ♦ ^ OCH₃

//

OHs-C^

(KII

©,

r. r

HjC'y ~-§_H, h8''^<V"CH₁ ^/    CjH;

. S

HjC cą

©/

CgHs-C^

OH

OCH₃

0>Hf

OH ^CjH₇ CjH-OH    I ©/

och₃ h