Nucleophilic Substitution

[Soaring Crane]

1) Predict the relative reaction times from fastest to slowest for the following compounds with NaI in acetone: 1-chlorobutane, 1-bromobutane, 2-chlorobutane.

I am assuming that this is under SN2 reaction conditions with the solvent and compound given.


2-chlorobutane = secondary substrate = slowest
1-bromobutane = primary substrate = fastest (Br is larger than Cl)
1-chlorobutane = primary substrate = moderate rate

2) Indicate whether the following statements refer to SN1 or SN2 reactions.

tertiary alcohols - SN1??
sp2 planar like transition state - SN1?? I am unsure of this one.
reaction rate independent of the concentration and nature of nucleophile = SN1??
inversion and retention of stereochemistry - SN2??
primary and secondary alcohols - SN2???
carbocation intermediate - SN1 ??

Thanks.

[sicjeff]

You are correct in your assumptions. I performed a similar experiment just yesterday for my organic lab.