haloform hickups !

why doesn't acetic acid respond to haloform test ?(you can also consider why acetamide and acetyl chloride don't respond to this test though all have keto methyl groups )

6 Answers

19
Debotosh.. ·

no answers expected???? confirm ??? i will answer myself !!

1
rickde ·

the -OH, -NH2, donate lp so the H are not so acidic

19
Debotosh.. ·

@rickde.....please elaborate !!!!

19
Debotosh.. ·

Due to the development of acetate ion the fourth OH- attack the system thereby inhibiting the reaction !!!(i hope you know that haloform involves use of 4 OH- ions)

11
Devil ·

l.p. reduces positive charge on c-atom.....

1
rickde ·

l.p reduces positive charge on the carbonyl carbon. now the +ve charge is responsible for making the H in CH3 acidic by stabilising the carbanion formed after removal of the H
as the + charge intensity decreases the carbanion becomes less stable making the H less acidic
thus the removal of H becomes more harder making the haloform reaction less feasible

also the removal of H is the rate determining step

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