SN2, Sodium Iodide In acetone (NAI in Acetone SN1, Silver Nitrate in Ethanol (Ag

Question

SN2, Sodium Iodide In acetone (NAI in Acetone

SN1, Silver Nitrate in Ethanol (AgNO3 in EtOH)

With These:

2-bromobutane,= NO SN2 Reaction, but SN1 in 3 sec

1-bromobutane= SN2 56 sec

1-chlorobutane= NO RXN

2-chlorobutane,= NO RXN

bromocyclopentane, = SN1 in 1 sec

bromocyclohexane, =NO RXN

benzyl chloride, = SN2 in 1 sec, not really SN1 just cloudy

bromobenzene,= NO RXN

t-butylchloride=  SN1 in 1 sec

(a) Why each compound had the reactivity observed

(b) Reactivity in terms of structure

(c)Reactivity of compounds with similar structure

Explanation / Answer

The SN1 requires an ionization to give a carbocation. This can be favored with a good ionizing solvent like a water alcohol mixture.

The SN2 is a bit complicated because many strong nucleophiles are also strong bases. Things like HS- and CN- and I- are strong nucleophiles, but not too basic so give the SN2 reaction with a secondry substrate. Acetate ion, CH3C(O)O- also works, but is slower. OH-, CH3O- and other alkoxides are strong nucleophiles, but are also strong bases. The competing reaction with these is E2, not SN1. If 2-bromobutane reacts with hydroxide, any alcohol product will probably be from an SN2 reaction, but must of the product will probably be butenes from a competing E2 reaction

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