Identifying the Electrophile in But-2-ene and Bromine Reaction

[chewchun]

Homework Statement

But-2-ene reacts with bromine in the presence of concentrated aqueous sodium nitrate to give the following compound
CH3-C(H)(ONO2)-C(H)(Br)-CH3

Which of the following statement is correct.
a.the electrophile is NO2+
b.Only 2,3-dibromobutane is formed.
c.Resultant solution shows optical activity.
d.Mechanism involves an initial electrophilic attack followed by nucleophilic attack

Homework Equations

The Attempt at a Solution

I know that B is out cause you can have -Br and -OH instead of just 2-Br.
C is also out because the compound can be attacked from both side(Trigonal planar)
A or D is correct.D makes sense to me but isn't NO2+ a electrophile. In this case i would presume NO2+ is somehow formed which attacks OH group...If not what is the case?

 

[AGNuke]

See, the halide molecule also polarize and form halide electrophile, in this case, Br⁺ can form. NaNO₃ cannot give NO₂⁺ ion, as it is obtained by "protonation" of nitric acid, which is not a simple task, considering nitric acid itself is very strong acid. That's what I feel.

 

[chemisttree]

Name these ions... NO₃^- and NO₂⁺

Which one is present in your proposed mixture?

 

[AGNuke]

CH3-C(H)(ONO2)-C(H)(Br)-CH3

Care to elaborate, as chemisttree asked?

UPDATE: I have formed on paper the compound H₃C-CH(ONO₂)-CHBr-CH₃, considering Nitrate group, albeit I am afraid I may have have bent some rules (which looks like the case, forming acid out of aqueous nitrate ions) And I have reached to following answers: C, D.

 

[chewchun]

CH3-C(H)(ONO2)-C(H)(Br)-CH3

Care to elaborate, as chemisttree asked?

UPDATE: I have formed on paper the compound H₃C-CH(ONO₂)-CHBr-CH₃, considering Nitrate group, albeit I am afraid I may have have bent some rules (which looks like the case, forming acid out of aqueous nitrate ions) And I have reached to following answers: C, D.

The answer was given to be D only.
The carbon is directly bonded to oxygen,and the oxygen directly bonded to NO2.So it seems to be O- and NO2+?And i presume the O- to be created from a alcohol group and the H+ is removed...
Answer is not C as the compound is trigonal planar and can be attacked from both sides,hence a racemic mixture..
But i don't understand how C(O)(NO2) is formed as it seems impossible to form NO2+ from this reaction...

 

[AGNuke]

Esterification I guess.