Choose the best set of reaction conditions

Br

H H

K OtButBuOH

HBr (aq)

100 oC

NaOH

EtOH/H2O

55 oC

A

B

C

Choose the best set of reaction conditions

Br

H H

K OtButBuOH

HBr (aq)

100 oC

NaOH

EtOH/H2O

55 oC

A

B

C

Hoffmann elimination: bulky strong base

Choose the best set of reaction conditions

A

B

C

Br

Br

Br

HO

NaOH, H2OEtOH

NaNH2, then H2O

NaOH, H2O

200 oC

Choose the best set of reaction conditions

A

B

C

Br

Br

Br

HO

NaOH, H2OEtOH

NaNH2, then H2O

NaOH, H2O

200 oC

SN2 displacement: low temperature, good nucleophile.

Choose the best set of reaction conditions

A

B

C

ClOH OH

H3O

100 oC

NaHCO3

H2O

100 oC

NaNH2, ether

Choose the best set of reaction conditions

A

B

C

ClOH OH

H3O

100 oC

NaHCO3

H2O

100 oC

NaNH2, ether

E1 elimination: polar solvent, high temperature, weak base

Choose the best set of reaction conditions

A

B

C

O

CH3 CH3

OH

CC

CH3

CH3

Br

Br

NaOH (aq.)

C CH3C Li

ether

C CH3C H

NaOH (aq.)

Choose the best set of reaction conditions

A

B

C

O

CH3 CH3

OH

CC

CH3

CH3

Br

Br

NaOH (aq.)

C CH3C Li

ether

C CH3C H

NaOH (aq.)

Acetylide (alkyne) anions are good SN2 nucleophiles but require non-aqueous conditions.

Choose the best set of reaction conditions

A

B

C

H3C

OH

CH3 H3C

O

CH3

CrO3, H3O+

Na2Oacetone,

Zn, HOAc

Choose the best set of reaction conditions

A

B

C

H3C

OH

CH3 H3C

O

CH3

CrO3, H3O+

Na2Oacetone,

Zn, HOAc

Chromium (VI) is used to oxidize alcohols to carbonyls.