Concept:Vicinal dibromides react with excess
NaNH2 to undergo double dehydrohalogenation, forming alkynes.
Hydration of terminal alkynes using
HgSO4 / dil
H2SO4 yields methyl ketones (
RCOCH3), which give a positive iodoform test but a negative Tollens test.
Explanation:Compound
P has the molecular formula
C9H10Br2.
Excess sodamide eliminates two molecules of
HBr from the vicinal dibromide, producing an alkyne
Q.
Upon adding dilute
HCl, the alkyne is protonated and obtained as the neutral compound
Q.
Treatment of
Q with
HgSO4 and dilute
H2SO4 adds water across the triple bond (Markovnikov addition).
For a terminal alkyne (
RC≡CH), the product is a methyl ketone (
RCOCH3).
This methyl ketone gives a positive iodoform test (due to the
CH3CO group) but a negative Tollens test (it is not an aldehyde).
Therefore,
Q must be a terminal alkyne, and
P must be a vicinal dibromide that can eliminate to form
C6H5CH2C≡CH (benzylacetylene).
Among the given options, only the structure
C6H5CH2CHBrCH2Br (option B) has two bromine atoms