Organic Chemistry Chapter 6 Part 2

WHat is the rate of the SN1 reaction

rate = k [alkyl halide] —> independent of the nucleophile

What are the steps of the SN1 reaction?

1. Formation of the carbocation

2. Attack of nucleophile

What is the occasional step 3 in SN1?

if the nucleophile is an uncharged molecule like water or alcohol, the positively charged product must lose a proton to give the final uncharged product

What is the rate limiting step in the SN1 reaction?

formation of the carbocation

What does the order of reactivity for alkyl halide degrees follow for SN1?

that of the stability of carbocations

3>2>1>CH3X

because the more stable carbocation requires less energy to form

What type of solvent is best for SN1?

polar protic solvent because it can solvate both ions strongly through hydrogen bonds

What happens to the structure of the compound after SN1?

you can get either R or S, forming racemic mixtures

What is the inductive effect>

where electron density is pushing into a position of less electron density

What are carbocations stabilized by?

inductive effect and hyperconjugation

WHat is hyperconjugation?

electrons that can be spread over the next few molecules of a molecule

What are the two different types of rearrangements?

hydride shift and methyl shift

What happens in the hydride shift?

the hydrogen on the adjacent carbon moves

What happens in the methyl shift?

the CH3 on the adjacent carbon moves

Why do rearrangements occur?

it can move the open position for bonding of the nucleophile to a more favorable 3 prime position.