Select the reagent that will yield the greater amount of substitution on reaction with `CH_3 -CH_2` - Br:
A
`CH_(3)CH_(2)OK` in dimethyl sulfoxide (DMSO)
B
`(CH_3)_2COK` in dimethyl sulfoxide (DMSO)
C
Both (a) and (b) will give comparable amounts ofsubstitution
D
Neither (a) nor (b) will give any amount ofsubstitution
Text Solution
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The correct Answer is:
A
Nucleophilicity `prop (1)/("size of "Nu^@)`
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Olefins can be halogenated in the allylic position by number of reagents of which N-bromo succinimide (NBS) is the most common. When this reagent is used the reaction is known as WohlZiegler bromination. Other N-bromoamides have also been used. To a much lesser extent allylic chlorination has been carried out with N-chloro-succinimide. N-Chloro-N-cyclohexyl benzene sulphonamide or t-hypochlorite when the allylic radical intermediate is unsymmetrical allylic rearrangement takes place so that the mixture of both possible products is obtained. CH_3 - CH_2 -CH = CH_2underset(hv)overset(NBS)(to) CH_3 - CH = CH - CH_2 - Br + CH_3 - undersetoverset(|)(Br)(C ) - CH = CH_2 NBS is also a highly regioselective brominating agent at other positions, including positions a to a carbonyl group.
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