Using 2-bromobutane as your starting material, write a generic equation for each condition indicating the expected...

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

Solutions

Expert Solution

1-bromobutane(n-butyl bromide)=it will give SN2 mechanism beacause the degree of carbon is 1^o . SN2 requires less crowded substrate and Polar aprotic solvent for substitution.

1-chlorobutane : it will give SN2 mechanism beacause the degree of carbon is 1^o . 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 1^o . 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 1^o . 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

queen_honey_blossom answered 3 weeks ago

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