Alkyl Halides

Ques) Among the following, the compound which does not forms a white precipitate on treatment with NaI in acetone is :-
(a) CH3 CH2 I (b) CH3 CH2 C l (c) Ph CH2 C l (d) CH2 = CH - CH2 C l

C l dentoes chlorine

9 Answers

106
Asish Mahapatra ·

(a) ?

3
iitimcomin ·

a??? [just a guess!!!]

11
Tush Watts ·

yeah it's (a), but what's the reason ?????

3
iitimcomin ·

sry didnt see ur post asish ......

106
Asish Mahapatra ·

There's ethyl iodide,, so if it reacts with NaI it wont form anything. sincewe already have I there

11
Tush Watts ·

ok thanx Asish [1]

13
Avik ·

Doubt frm my side--- In this Halide Exchange rxn, how come I- being a weaker Nucleophile than Cl- , is able to replace it ??

1
Ankur ·

yeah you can say it's halide exchange method. And precipitate will only occur when a group other than AgI is formed like AgCl or AgBr, these are the only ppts (you must have done practicals, AgCl ppt is not soluble in AgNO3, AgBr is partially soluble while AgI is completely soluble).
Hope this clears!

11
Tush Watts ·

@ AVIK

The feasibility of this reacn is due to solubility of Na I in acetone and more nucleophilic character of I- ion . The reaction proceeds by SN 2 mechanism and is possible bcoz Na Cl and Na Br are precipitated in this reaction , as they are not soluble in weakly polar aprotic solvent.

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