In: Chemistry
Using 2-bromobutane as your starting material, write a generic equation for each condition indicating the expected products and show the two possible mechanisms for nucleophilic substitutions.
1-bromobutane (n-butyl bromide)
1-chlorobutane
3-bromopropene (allyl bromide)
2-chlorobutane
2-bromobutane (sec-butyl bromide)
2-chloro-2-methylpropane
2-bromo-2-methylpropane (t-butyl-bromide)
chlorobenzene
1-bromobutane(n-butyl bromide)=it will give SN2 mechanism beacause the degree of carbon is 1o . SN2 requires less crowded substrate and Polar aprotic solvent for substitution.
1-chlorobutane : it will give SN2 mechanism beacause the degree of carbon is 1o . SN2 requires less crowded substrate and Polar aprotic solvent for substitution.It will be slower than bromosubstitution because Br is better leavin group than Cl
3-bromopropene (allyl bromide) : It will give SN1and SN2 both , allylic substitution is favored
2-chlorobutane : it will give SN2 mechanism beacause the degree of carbon is 1o . SN2 requires less crowded substrate and Polar aprotic solvent for substitution.It will be slower than bromosubstitution because Br is better leavin group than Cl
2-bromobutane (sec-butyl bromide) : it will give SN2 mechanism beacause the degree of carbon is 1o . SN2 requires less crowded substrate and Polar aprotic solvent for substitution.It will be slower than bromosubstitution because Br is better leavin group than Cl
2-chloro-2-methylpropane : It will give SN1 best, beacause carbocation is the intermediate, so it will be more stable, greater is the stability greater is the rate of SN1
2-bromo-2-methylpropane (t-butyl-bromide): It will give SN1 best, beacause carbocation is the intermediate, so it will be more stable, greater is the stability greater is the rate of SN1
chlorobenzene : It will neither give SN1 nor SN2 , because of partial double bond character of halogen carbon bond in chlorobenzene