1) The reactions are either SN1, SN2, both or neither mechanisms. SN1 favors good leaving groups and SN2 favors primary/secondary carbons.
2) Bromide is a better leaving group than chloride, so the top reaction will be faster. For the sulfide reactions, the 3° carbon makes it an SN1 process occurring at the same rate.
3) Beta-branching retards the SN2 reaction on the lower substrate. SN2 is also faster in polar aprotic solvents like DMSO compared to protic solvents like methanol.
1) The reactions are either SN1, SN2, both or neither mechanisms. SN1 favors good leaving groups and SN2 favors primary/secondary carbons.
2) Bromide is a better leaving group than chloride, so the top reaction will be faster. For the sulfide reactions, the 3° carbon makes it an SN1 process occurring at the same rate.
3) Beta-branching retards the SN2 reaction on the lower substrate. SN2 is also faster in polar aprotic solvents like DMSO compared to protic solvents like methanol.
1) The reactions are either SN1, SN2, both or neither mechanisms. SN1 favors good leaving groups and SN2 favors primary/secondary carbons.
2) Bromide is a better leaving group than chloride, so the top reaction will be faster. For the sulfide reactions, the 3° carbon makes it an SN1 process occurring at the same rate.
3) Beta-branching retards the SN2 reaction on the lower substrate. SN2 is also faster in polar aprotic solvents like DMSO compared to protic solvents like methanol.
1) The reactions are either SN1, SN2, both or neither mechanisms. SN1 favors good leaving groups and SN2 favors primary/secondary carbons.
2) Bromide is a better leaving group than chloride, so the top reaction will be faster. For the sulfide reactions, the 3° carbon makes it an SN1 process occurring at the same rate.
3) Beta-branching retards the SN2 reaction on the lower substrate. SN2 is also faster in polar aprotic solvents like DMSO compared to protic solvents like methanol.
Question One For each of the f ollowing reactions, give the structure of the product and indicate whether the mechanism is likely to be SN1, SN2, both or neither.
SN1 CH3CH2OH Cl OCH2CH3
Br I NaI, Acetone SN2
Cl
NaOH No reaction
Br CH3SNa SCH3 SN2
Ph C C CH3CH2Br Ph SN2
Cl OH NaOH SN1 and/or SN2
Cl CH3CH2OH OCH2CH3 SN1 Question Two For each of the f ollowing pairs, which reaction, if either, will be f aster?
CH3OH Bromide is the better leaving
Br group. The top reaction will be OCH3 f aster.
CH3OH Cl OCH3
CH3S 3° substrate, so this is an SN1
Br SCH3 process. While the anionic sulf ide is a better nucleophile, the nucleophile is not involved in the rate determining step of SN1. CH3SH Br SCH3 Both reactions will occur at the same rate.
Br beta-Branching will NaCN CN retard the SN2 reaction of the lower substrate.
NaCN Br CN
Br NaCN CN DMSO
Br NaCN CN CH3OH SN2 reactions are f aster in polar aprotic solvents like DMSO.
