williamson ether synthesis

i wanna produce ch3oet by william son ether synthesis
should i take ch3ona+eti or etona+ch3i
which give better yield???????

8 Answers

24
eureka123 ·

Williamson involves SN2 attack of alkoxide on alkyl halide............so for better reaction we have to identify better leaving group.
CH3I=super primary(as sky said)[3]
EtI=1°

so 2nd combination will give better yield.[1]

1
skygirl ·

for this u need to know the mechanism :)

see ... RNa has R- and Na+ .

this R- goes and attack R'I from behind ... and I- leaves..

so wat we can conclude??

>> R should be a good nucleophile..

>> I should be attached to such an alkyl chain where it will
not 'leave' n go away easily (like 3°) ... [since -I is a very very good leaving group]

now in the present case,

Et- is a better nucleophile than Me- .

so, it should be: CH3I and EtONa..

1
skygirl ·

@eureka...

u wrote : CH3I=3°

[7] [7] [7] [7]

typo i hope ??

1
voldy ·

no dude ,it's not even a primary halide , I think . well ther's only one C where 10 or 20 . I dunno might b wrong

1
skygirl ·

both are primary.. but..

the thing is that:

EtI will produce a more stable carbocation [hyperconjugation!]

so we will use CH3I and EtONa ...

1
skygirl ·

sorry ...its super-primary [3]

but think hyperconjugation here....

24
eureka123 ·

are yaar.........kya kar rahe ho....bhavnao ko samjho........[3]

1
skygirl ·

kiski bhavna?

aur kaunsi bhavna?

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