Question

Write the equation and mechanism of ONLY the THEORETICALLY fastest reaction that should have

occurred. Equation should be written with starting materials on one side and product on the other. Mechanism should have the species with arrows depicting movement of electrons with intermediates showing (where applicable)
You should have a total of 3 equations and 3 mechanisms
Use actual alkyl halide and reagent (no R-X and Nu)

Alkyl halides used in this Experiment
1-chlorobutane
1-bromobutane
2-chlorobutane
2-chloro-2-methylpropane
2-bromobutane
Bromobenzene

I) Reacting the 6 alkyl halides with sodium iodide in acetone.
II) Reacting the 6 alkyl halides with silver nitrate in ethanol
III) Reacting 2-chloro-2-methylpropane with silver nitrate in 50% ethanol: 50% water

Answer 1

The answer discusses the SN1 and SN2 reaction mechanisms for the fastest theoretical reactions involving various alkyl halides with sodium iodide in acetone and silver nitrate in ethanol, highlighting tertiary carbocations, backside nucleophilic attacks, and stereochemistry inversion.

Step-by-step explanation:

This answer provides insight into the theoretically fastest reaction mechanisms of alkyl halides with different reagents. The three theoretically fastest reactions to be considered, based on the alkyl halides provided, involve:

1. 2-chloro-2-methylpropane reacting with sodium iodide in acetone, which will proceed through an SN1 mechanism due to the highly substituted tertiary carbon, enabling the formation of a stable carbocation.
2. 1-bromobutane reacting with silver nitrate in ethanol, which is expected to undergo an SN2 mechanism, as it is a primary alkyl halide with a good leaving group and will favor a backside attack mechanism.
3. 2-chloro-2-methylpropane reacting with silver nitrate in a mixed solvent system (50% ethanol and 50% water), which again, due to steric hindrance and carbocation stability, favors an SN1 mechanism.

The balanced reaction equations and detailed mechanisms showing the electron movements for these reactions would outline the formation of products from the specific starting materials and would depict intermediates where applicable.

Each mechanism would reflect electron donation from the nucleophile (NaI or AgNO3) to the electrophilic carbon within the alkyl halides and the subsequent release of the leaving group (Cl or Br). In the case of SN1 mechanisms, the formation of a carbocation intermediate would be shown before the nucleophilic attack. For SN2 mechanisms, the nucleophile would attack the alkyl halide in a concerted step with inversion of stereochemistry.