Clickers: Which one of the following reactions would actually work as written?
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Transcript of Clickers: Which one of the following reactions would actually work as written?
![Page 1: Clickers: Which one of the following reactions would actually work as written?](https://reader037.fdocuments.in/reader037/viewer/2022090103/5a4d1baf7f8b9ab0599cc102/html5/thumbnails/1.jpg)
Clickers:Which one of the following reactions would actually work as written?
H3C
O
H
BuLi, THF, -78 oC
then add2-chloropropane
O
HH3C
CH3A
H3C O
OCH3
NaOH (aq.)
EtBr O
OCH3H3C
B
H3C CH3
O NaOH (aq.)
80 oC H3C
O
CH3
CH3
C
D CH3
OH
H3C CH3
LDA, THF-78 oC
then add2-chloropropane
CH3
O
H3C CH3
CH3
H3C
![Page 2: Clickers: Which one of the following reactions would actually work as written?](https://reader037.fdocuments.in/reader037/viewer/2022090103/5a4d1baf7f8b9ab0599cc102/html5/thumbnails/2.jpg)
Aldol condensation of ketone driven to completion by elimination (high temp).
Clickers:Which one of the following reactions would actually work as written?
H3C
O
H
BuLi, THF, -78 oC
then add2-chloropropane
O
HH3C
CH3A
H3C O
OCH3
NaOH (aq.)
EtBr O
OCH3H3C
B
H3C CH3
O NaOH (aq.)
80 oC H3C
O
CH3
CH3
C
D CH3
OH
H3C CH3
LDA, THF-78 oC
then add2-chloropropane
CH3
O
H3C CH3
CH3
H3C
![Page 3: Clickers: Which one of the following reactions would actually work as written?](https://reader037.fdocuments.in/reader037/viewer/2022090103/5a4d1baf7f8b9ab0599cc102/html5/thumbnails/3.jpg)
Clickers:What product would be isolated after workup?
O
O
KOH (aq.)
O
D
C
B
A
O
O
HO
O
OH
![Page 4: Clickers: Which one of the following reactions would actually work as written?](https://reader037.fdocuments.in/reader037/viewer/2022090103/5a4d1baf7f8b9ab0599cc102/html5/thumbnails/4.jpg)
Equilibrium conditions, 5-membered ring therefore get rapid elimination to thermodynamically-favoured enone isomer
Clickers:What product would be isolated after workup?
O
O
KOH (aq.)
O
D
C
B
A
O
O
HO
O
OH
![Page 5: Clickers: Which one of the following reactions would actually work as written?](https://reader037.fdocuments.in/reader037/viewer/2022090103/5a4d1baf7f8b9ab0599cc102/html5/thumbnails/5.jpg)
Clickers:Which of the following would least likely form a nucleophilic carbanion on treatment with a base?
O
NO2
CN
CCH
OH
A
B
C
D
E
![Page 6: Clickers: Which one of the following reactions would actually work as written?](https://reader037.fdocuments.in/reader037/viewer/2022090103/5a4d1baf7f8b9ab0599cc102/html5/thumbnails/6.jpg)
O-H 15 - 17; C-H approx 50!
Clickers:Which of the following would least likely form a nucleophilic carbanion on treatment with a base?
O
NO2
CN
CCH
OH
A
B
C
D
E
Approx. pKa
19 - 20
25
24 - 25
10 - 11