on the basis of my results arrange these halogen containing compounds in order o

Question

on the basis of my results arrange these halogen containing compounds in order of decreasing reactivity for 1) sn1 reactions 2) sn2 reactions

silver nitrate test results (SN1 mechanism)

1-chlorobutane: occured only slowly over hot water

2- chlorobutane: occured only slowly over hot water

2-chloro-2-methylpropane: cloudy. reaction occured

1-bromobutane: occured slowly but WITHOUT HOT WATER

2-bromobutane: cloudy, reaction occured

chlorobenzene: clear. NO REACTION

benzyl chloride: occured slowly but WITHOUT HOT WATER

3-chloro-1-butene: cloudy. reaction occured

bromocyclohexane: cloudy. reaction occured

bromocyclopentane: cloudy. reaction occurred.

beta-bromostyrene: This molecule doesn't undergo sn1 reaction, but im not sure how the addition reaction would look like.

ii) Sodium iodide test ( sn2 mechanism)

1-chlorobutane: reaction only occurs in hot water

2-chlorobutane: no reaction

2-chloro-2-methylpropane: no reaction

1-bromobutane: reaction occurs immediately

2-bromobutane: reaction only occurs in hot water

chlorobenzene: no reaction

benzyl chloride: reaction occurs immediately

3-chloro-1-butene: reaction occurs immediately

bromocyclohexane: no reaction

bromocyclopentane: reaction only occurs in hot water

beta bromostyrene: false sn2 reaction

Explanation / Answer

SN1 mechanism

3-chloro-1-butene > 2-chloro-2-methylpropane   > 2-bromobutane > bromocyclopentane > bromocyclohexane > 2- chlorobutane > 1-bromobutane > 1-chlorobutane > chlorobenzene > beta-bromostyrene

SN2 mechanism

1-bromobutane > 1-chlorobutane > 2-bromobutane > bromocyclopentane > benzyl chloride > 3-chloro-1-butene

Related Questions

Navigate

• Browse (All)
• Browse O
• Subjects

Integrity-first tutoring: explanations and feedback only — we do not complete graded work. Learn more.