Anti or Syn

+ (i) Hg(OAc)2/HOH/THF ---> ??
(ii) NaBH4/NaOH

There will be anti addition of water or syn addition ??

11 Answers

39
Pritish Chakraborty ·

As the demercuration step involves radical reactions, the stereochemistry of this reaction is scrambled. It undergoes overall syn as well as overall anti addition.
The oxymercuration step is syn, though. But after demercuration, both anti and syn products are obtained.

11
Gone.. ·

thanks Pritish..this is what i wanted to confirm.

1
rickde ·

in OMDM (1) is is anti addition

in HYDroboration is syn addition

see the intermediates

1
rickde ·

@ pritish
why... the cyclic intermediate formed after oxymercuration will be attacked from the opp side by water....so shouldn't it be anti???????

39
Pritish Chakraborty ·

oh ya oxymercuration is anti....mercurinium bridged ion is formed which is attacked by water in SN2 type reaction(backside) leading to anti product...overall products are still syn and anti however!
thanks rickde :)

1
Parjanya ·

yeah Rickde is correct, i totally agree wid him

11
Gone.. ·

thanks guys [1]

1
ankit goel ·

ya i also think rickde is right

13
deepanshu001 agarwal ·

what wud hav bin d ans in case d substrate ws trans.....?

1
Parjanya ·

@ Deepanshu even if d substrate was trans d addition wud b same bt products wll b different
like wen der is anti addition wid d trans alkene d products formed r meso &
wen der is syn addition is der wid trans alkene d product formed is racemic

remember dis
cis alkene + syn addition = product is meso
cis alkene + anti addition = product is racemic
trans alkene + syn addition = product is racemic
trans alkene + anti addition = product is meso

13
deepanshu001 agarwal ·

@ parjanya
lady i knw tht
bt wt i ve heard is tht hydroboration exclusively gives syn addition product....
olso u wont get any meso products here ....

so i guess answrs here shud be d same bt i m nt sure

btw i lykd ur punchlyn......! awesum

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