Reactions of Alkyl Halides
Terms in this set (10)
What are the 4 reactions of alkyl halides other than Sn1, Sn2, E1, and E2?
reduction, coupling, dehydrohalogenation (elimination). metalation (substitution)
What are the reactants of reduction, coupling, dehydrohalogenation, and metalation?
Li, CuI→ something similar to CH₂CHCl
NaOH→ alcohol and heat
NaNH₂ → addition group
What can't you do an SN2 reaction on?
an sp² carbon; has to have an sp³
What are the 4 factors that affect Sn1 and SN2 reactions?
-nature of the reaction center
-nature of the nucleophile
-nature of the leaving group
Nature of the reaction center for Sn1 and Sn2
Sn2- can't do it on a tertiary carbon due to steric crowding
Sn1- can't do it if on a primary carbon due to carbocation stability
Nature of the nucleophile for Sn2 and Sn1
Sn2- as nucleophilicity increases, reaction rate increases and favors Sn2
Sn1- nucleophilic character does not matter
(nucleophilicity usually parallels base strength)
Nature of the leaving group for Sn2 and Sn1
Sn2- wants to have a negative charge
Sn1- charge doesn't matter
-good leaving groups accelerate the reaction
What is a good leaving group?
a stable anion or a weak base
Solvent character of Sn2 and Sn1
Sn2 and Sn1- polar solvents accelerate the reaction
Sn1 is not possible in a nonpolar solvent
Why does Sn1 have to have polar solvents?
polar solvents stabilize the carbocation