Let’s analyze each compound to determine whether it undergoes SN1 in AgNO3, SN2 in NaI, or both.
1-Chlorobutane
SN1 in AgNO3: 1-Chlorobutane is a primary alkyl halide. Primary alkyl halides generally do not undergo SN1 reactions because they form unstable carbocations. Therefore, 1-Chlorobutane is unlikely to react via SN1 in AgNO3.
SN2 in NaI: Primary alkyl halides are ideal for SN2 reactions due to less steric hindrance. Therefore, 1-Chlorobutane will undergo an SN2 reaction with NaI, where I- will replace the Cl-.
1-Bromobutane
SN1 in AgNO3: Similar to 1-Chlorobutane, 1-Bromobutane is also a primary alkyl halide and will not undergo SN1 reactions due to the instability of primary carbocations.
SN2 in NaI: 1-Bromobutane will undergo an SN2 reaction with NaI, where I- will replace the Br-.
2-Chlorobutane
SN1 in AgNO3: 2-Chlorobutane is a secondary alkyl halide. Secondary alkyl halides can undergo SN1 reactions, but the reaction is slower compared to tertiary alkyl halides. Therefore, 2-Chlorobutane may undergo SN1 in AgNO3, but the reaction will be slow.
SN2 in NaI: Secondary alkyl halides can also undergo SN2 reactions, but the reaction is slower compared to primary alkyl halides due to increased steric hindrance. Therefore, 2-Chlorobutane will undergo an SN2 reaction with NaI, but the reaction will be slower than with primary alkyl halides.
t-Butyl Chloride (t-BuCl)
SN1 in AgNO3: t-Butyl Chloride is a tertiary alkyl halide. Tertiary alkyl halides are ideal for SN1 reactions because they form stable carbocations. Therefore, t-Butyl Chloride will readily undergo SN1 in AgNO3.
SN2 in NaI: Tertiary alkyl halides are highly sterically hindered, making SN2 reactions very difficult. Therefore, t-Butyl Chloride will not undergo an SN2 reaction with NaI.
In summary:
- 1-Chlorobutane: SN2 in NaI
- 1-Bromobutane: SN2 in NaI
- 2-Chlorobutane: Both SN1 in AgNO3 (slow) and SN2 in NaI (slow)
- t-Butyl Chloride: SN1 in AgNO3