E2 Mechanism Work through each problem before looking at the answer key below.

Consider only the E2 reaction. If more than one product is possible, indicate which is preferred.

CH3 CH3CH2ONa
H3C C OTs CH3CH2OH
CH3

CH3 CH3ONa
CH3OH
Cl hot

Cl CH3CH2ONa
EtOH
warm

CH3CH2ONa
70oC
Br EtOH
OK

Br (CH3)3COH

I CH3CH2ONa
EtOH
CH3

I ONa
CH3 CH3 (CH2)6CH2OH
warm
OTs
CH3CH2ONa
EtOH
warm
CH2CH3
CH3CH2ONa
EtOH
70oC
Br
CH3
 ANSWER KEY
Consider only the E2 reaction. If more than one product is possible, indicate which is preferred.

CH3 CH3CH2ONa CH2

H3C C OTs CH3CH2OH H3C C
CH3 CH3

CH3 CH3ONa CH3 CH3

CH3OH +
Cl hot preferred

Cl CH3CH2ONa
EtOH + + unlikely
preferred
warm

preferred
CH3CH2ONa
70oC +
Br EtOH
OK

Br (CH3)3COH

I CH3CH2ONa CH3 CH2

EtOH
+
CH3 preferred

I ONa CH2

CH3 CH3 (CH2)6CH2OH

warm
OTs
CH3CH2ONa
EtOH
warm
CH2CH3 CH2CH3
CH3CH2ONa
EtOH
70oC
Br only
CH3 CH3