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

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

Clickers:What product would be isolated after workup?

O

O

KOH (aq.)

O

D

C

B

A

O

O

HO

O

OH

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

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

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